United States v. Martinez-Maldonado, 1st Cir. (2013)

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    United States Court of AppealsFor the First Circuit

    Nos. 12- 1289, 12- 1290

    UNI TED STATES OF AMERI CA,

    Appel l ee,

    v.

    J UAN BRAVO FERNANDEZ; HECTOR MART NEZ MALDONADO,

    Def endant s, Appel l ant s.

    APPEALS FROM THE UNI TED STATES DI STRI CT COURTFOR THE DI STRI CT OF PUERTO RI CO

    [ Hon. Franci sco A. Besosa, U. S. Di st r i ct J udge]

    Bef or e

    Howar d, Li pez, and Thompson,Ci r cui t J udges.

    Mar t i n G. Wei nber g, wi t h whom Davi d Z. Chesnof f , Chesnof f &Schonf el d, Ki mber l y Homan, J ose A. Pagan, and Pagan Law Of f i ceswer e on br i ef , f or appel l ant Br avo Fer nandez.

    Abbe Davi d Lowel l , wi t h whomChr i st opher D. Man and Chadbour ne& Par ke LLP wer e on br i ef , f or appel l ant Mar t nez Mal donado.

    Pet er M. Koski , Deput y Chi ef , Cr i mi nal Di vi si on, Publ i cI nt egr i t y Sect i on, Uni t ed St at es Depar t ment of J ust i ce, wi t h whomLanny A. Br euer , Assi st ant At t or ney Gener al , and Mar y Pat r i ceBr own, Deput y Assi st ant At t or ney Gener al , wer e on br i ef , f orappel l ee.

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    J une 26, 2013

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    LIPEZ, Circuit Judge. Thi s case pr esent s mul t i pl e i ssues

    of subst ant i al i mpor t ance, i ncl udi ng a quest i on of f i r st i mpr essi on

    i n t hi s ci r cui t on t he i nt er pr et at i on of t he f eder al pr ogr am

    br i ber y st at ut e, 18 U. S. C. 666. Def endant s ar e a Puer t o Ri co

    l egi sl at or and a Commonweal t h busi nessman who wer e char ged, i nter

    al i a, wi t h unl awf ul l y exchangi ng a t r i p t o Las Vegas t o at t end a

    pr i ze f i ght f or f avor abl e acti on on l egi sl at i on. A j ur y r et ur ned

    gui l t y ver di ct s agai nst bot h men, J uan Br avo Fer nandez ( "Br avo")

    and Hect or Mar t nez Mal donado ( "Mar t nez") , and t hey now chal l enge

    t hei r convi ct i ons on numer ous gr ounds. For emost i s t hei r

    cont ent i on t hat t he j ur y was al l owed t o convi ct on a gr at ui t y

    t heor y whi ch i s beyond the scope of 666.

    Unl i ke most ci r cui t s t o have addr essed t hi s i ssue, we

    concl ude t hat 666 does not cr i mi nal i ze gr at ui t i es. Because t he

    di str i ct cour t ' s i nstr uct i ons per mi t t ed t he j ur y t o f i nd gui l t on

    t he 666 count s based on a gr atui t y t heory, Def endant s'

    convi ct i ons on t hat count must be vacat ed. I n addi t i on, we

    concl ude t hat t he Doubl e J eopardy Cl ause, t hough f or r easons t hat

    di f f er f or each Def endant , ent i t l es bot h men t o acqui t t al on t hei r

    r espect i ve conspi r acy char ges.

    I.

    A. Factual Background

    We br i ef l y summar i ze t he r el evant f act s, r eser vi ng f or

    our anal ysi s a mor e det ai l ed di scussi on of t he f act s r el evant t o

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    each i ssue pr esent ed on appeal . We vi ew t he f act s i n t he l i ght

    most f avor abl e t o t he j ur y' s ver di ct s. See Uni t ed St at es v.

    Ci r esi , 697 F. 3d 19, 23 ( 1st Ci r . 2012) .

    From J anuar y 2005 unt i l ear l y 2011, Mar t nez ser ved i n

    t he Senat e of t he Commonweal t h of Puer t o Ri co. 1 When Mar t nez

    became a senat or he was ass i gned t o t he Publ i c Saf et y Commi t t ee,

    wher e he ser ved as chai r man. Br avo was t he presi dent of Ranger

    Amer i can, a pr i vat e f i r mt hat pr ovi des secur i t y ser vi ces, i ncl udi ng

    ar mor ed car t r anspor t at i on and secur i t y guar d st af f i ng.

    I n ear l y 2005, Br avo advocated f or t he passage of

    l egi sl at i on r el at ed t o t he secur i t y i ndust r y i n Puer t o Ri co. One

    of t hese bi l l s, Senat e Pr oj ect 410, addr essed i ssues per t ai ni ng t o

    secur i t y at shoppi ng mal l s, whi l e t he ot her , Senat e Pr oj ect 471,

    i nvol ved l i censi ng r equi r ement s f or ar mored car compani es. The

    gover nment pr oduced t est i mony at t r i al t hat t he passage of t hese

    bi l l s woul d have pr ovi ded subst ant i al f i nanci al benef i t s t o Ranger

    Amer i can. As chai r man of t he Publ i c Saf ety Commi t t ee, Mar t nez was

    i n a posi t i on t o exer ci se a measur e of cont r ol over t he

    i nt r oduct i on and pr ogr essi on of t he bi l l s t hr ough t he Commi t t ee and

    t he Senat e.

    1 The r ecor d does not speci f y t he dur at i on of Mar t nez' st enur e i n t he Puer t o Ri co Senat e. We t ake j udi ci al not i ce of t hef act t hat he r esi gned hi s seat i n ear l y 2011. See Fed. R. Evi d.201( b) ( al l owi ng a cour t t o t ake j udi ci al not i ce of a f act "notsubj ect t o r easonabl e di sput e because i t . . . can be accur at el yand readi l y det er mi ned f r om sour ces whose accur acy cannotr easonabl y be quest i oned") .

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    On May 14, 2005, pr omi nent Puer t o Ri can boxer Fl i x

    "Ti t o" Tr i ni dad was schedul ed t o f i ght Ronal d Lamont "Wi nky" Wr i ght

    at t he MGM Gr and Hot el & Casi no i n Las Vegas, Nevada. On Mar ch 2,

    Br avo pur chased f our t i cket s t o the f i ght at a cost of $1, 000 per

    t i cket . The same day, Mar t nez submi t t ed Senat e Proj ect 410 f or

    consi der at i on by t he Puer t o Ri co Senat e. On Apr i l 20, Mar t nez

    pr esi ded over a Publ i c Saf et y Commi t t ee hear i ng on Senate Pr oj ect

    471 at whi ch Br avo t est i f i ed. The next day, Br avo booked one r oom

    at t he Mandal ay Bay Hot el i n Las Vegas. On May 11, Mar t nez i ssued

    a Commi t t ee r epor t i n suppor t of Senate Proj ect 471.

    Br avo ar r anged f or f i r st - cl ass ai r l i ne t i cket s t o Las

    Vegas f or hi msel f , Mar t nez, and anot her senat or , J or ge de Cast r o

    Font . 2 I n Las Vegas, t he t hr ee men st ayed i n separat e r ooms at t he

    Mandal ay Bay f or t wo ni ght s. Br avo pai d f or Mar t nez' s r oom t he

    f i r st ni ght , and de Cast r o Font pai d f or Mar t nez' s r oomt he second

    ni ght . The men, al ong wi t h de Cast r o Font ' s assi st ant , went out t o

    di nner t he day bef or e t he f i ght , wi t h Br avo f oot i ng t he $495 bi l l .

    The men at t ended t he Ti t o Tr i ni dad f i ght t he next ni ght , usi ng t he

    $1, 000 t i cket s Br avo had pur chased.

    2 I n 2008, J or ge de Cast r o Font was i ndi ct ed on numerouscount s rel at i ng t o cor r upt i on by an el ect ed of f i ci al . See Uni t edSt at es v. De Cast r o- Font , 587 F. Supp. 2d 353, 355 ( D. P. R. 2008) .On J anuar y 29, 2009, de Cast r o Font pl ed gui l t y t o 21 count s of t hei ndi ct ment f i l ed agai nst hi m. He r ecei ved a sent ence of si xt ymont hs' i mpr i sonment . See Uni t ed St ates v. De Cast r o- Font , 08- CR-337- 01( FAB) , Doc. 353 (D. P. R. May 17, 2011) .

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    The day af t er t he f i ght , Br avo, Mar t nez, and de Cast r o

    Font f l ew f r om Las Vegas t o Mi ami , wher e they spent t he ni ght i n

    i ndi vi dual hotel r ooms at t he Mar r i ot t Sout h Beach. The r ooms wer e

    r eserved and pai d f or by Br avo at a t ot al cost of $954. 75. The

    next day, on May 16, t he thr ee r et ur ned t o Puer t o Ri co.

    On May 17, de Cast r o Font , act i ng as Chai r of t he

    Commi t t ee on Rul es and Cal endar s, schedul ed an i mmedi at e vot e on

    t he f l oor of t he Puer t o Ri co Senat e f or Senat e Pr oj ect 471. Bot h

    de Cast r o Font and Mar t nez vot ed i n suppor t of t he bi l l . The next

    day, Mar t nez i ssued a Commi t t ee repor t i n f avor of Senat e Pr oj ect

    410. On May 23, de Cast r o Font schedul ed an i mmedi at e vot e on t he

    f l oor of t he Senat e f or Senat e Pr oj ect 410. Agai n, bot h de Cast r o

    Font and Mar t nez vot ed f or t he bi l l .

    B. Procedural Background

    On J une 22, 2010, a grand j ur y retur ned an i ndi ct ment

    char gi ng Br avo and Mar t nez wi t h ( 1) vi ol at i ng 18 U. S. C. 371 by

    conspi r i ng t o ( a) commi t f eder al pr ogr ambr i ber y, and ( b) t r avel i n

    i nt er st at e commer ce i n ai d of r acket eer i ng; ( 2) vi ol at i ng 18 U. S. C.

    1952( a) ( 3) ( A) by t r avel i ng i n i nt er st at e commer ce wi t h the i nt ent

    t o "[ p] r omot e, est abl i sh, car r y on, and f aci l i t at e t he pr omot i on,

    est abl i shment , and car r yi ng on, " of unl awf ul acti vi t y, speci f i cal l y

    ( a) f eder al pr ogr am br i ber y i n vi ol at i on of 666, and ( b) br i ber y

    i n vi ol at i on of P. R. Laws Ann. , t i t . 33, 4360 and 4363; and ( 3)

    f eder al pr ogr am br i ber y i n vi ol at i on of 666. Mar t nez was

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    addi t i onal l y i ndi ct ed f or obst r uct i on of j ust i ce, i n vi ol at i on of

    18 U. S. C. 1512( b) ( 3) .

    The case went t o t r i al on Febr uary 14, 2011. On Mar ch 7,

    2011, a j ur y convi ct ed Br avo of conspi r acy t o t r avel i n i nt er st at e

    commer ce i n ai d of r acket eer i ng ( count one) , i nt er st at e t r avel i n

    ai d of r acket eer i ng wi t h t he i nt ent t o pr omot e br i ber y i n vi ol at i on

    of Puer t o Ri co l aw ( count t wo) , and f eder al pr ogr am br i ber y ( count

    f our ) . The j ur y f ound Mar t nez gui l t y of conspi r acy ( count one) ,

    but checked "No" as t o each potent i al obj ect of t he conspi r acy. He

    was al so convi ct ed of f eder al pr ogr am br i ber y ( count f i ve) . The

    j ur y acqui t t ed Mar t nez of i nt er st at e t r avel i n ai d of r acket eer i ng

    ( count t hr ee) and obst r uct i on of j ust i ce ( count si x) .

    The t r i al cour t gr ant ed Br avo' s mot i on f or j udgment of

    acqui t t al on count t wo, f i ndi ng t hat t he r epeal of t he Puer t o Ri co

    br i ber y l aws bef or e t he t r i p t ook pl ace made i t i mpossi bl e f or

    Br avo t o sat i sf y t he " t her eaf t er " el ement 3 of a Tr avel Act

    vi ol at i on. I t i ni t i al l y "di smi ssed" Mar t nez' s convi cti on on count

    one because t he j ur y rej ect ed bot h pot ent i al obj ect s of t he

    conspi r acy, but t hen " r ei nst at ed" t he convi ct i on t he next day, and

    event ual l y di smi ssed i t wi t hout pr ej udi ce. On March 1, 2012, t he

    di st r i ct cour t sent enced bot h def endant s t o 48 mont hs of

    3 See i nf r a Par t V.

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    i mpr i sonment . Br avo r ecei ved a f i ne of $175, 000 and Mar t nez a

    f i ne of $17, 500. 4

    C. Issues on Appeal

    Bot h Def endant s chal l enge t hei r subst ant i ve 666

    convi ct i ons on numer ous gr ounds. Mar t nez chal l enges on doubl e

    j eopar dy gr ounds t he di st r i ct cour t ' s deci si on t o r ei nst at e hi s

    conspi r acy convi ct i on and t hen di smi ss i t wi t hout pr ej udi ce. Br avo

    al so chal l enges hi s conspi r acy convi ct i on, ar gui ng, among ot her

    t hi ngs, t hat t he j udgment of acqui t t al on t he Tr avel Act count

    r equi r es t he ent r y of j udgment of acqui t t al on t he conspi r acy

    count , as 666, gi ven t he f i ndi ngs by t he j ur y, cannot ser ve as an

    obj ect of t he conspi r acy t o vi ol at e t he Tr avel Act .

    II.

    Def endant s r ai se sever al chal l enges t o t he scope of t he

    f eder al pr ogr ambr i ber y st at ut e, 18 U. S. C. 666, and, i dent i f yi ng

    cer t ai n el ement s of t he st at ut e, t hey al so cl ai m t hat t he

    ci r cumst ances of t hi s case do not sat i sf y any of t hose el ement s.

    We revi ew t he quest i ons of l aw r ai sed i n thei r argument s de novo,

    4 Br avo and Mar t nez bot h f i l ed mot i ons f or bai l pendi ngappeal bef or e t he di st r i ct cour t , and bot h mot i ons wer e deni ed.Mar t nez began ser vi ng hi s sent ence on March 1, 2012, whi l e Br avo

    began ser vi ng hi s on May 7, 2012. Br avo began ser vi ng hi s sent encel ater because of some heal t h i ssues. Def endant s subsequent l ybr ought t hei r mot i ons f or bai l pendi ng appeal bef or e us, and, i near l y March 2012, both wer e deni ed. Fol l owi ng oral argument i nNovember 2013, we r ecei ved Def endants' r enewed mot i ons f or bai lpendi ng appeal on December 11, 2012. They wer e grant ed on J anuar y2, 2013.

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    Uni t ed St at es v. Pl ace, 693 F. 3d 219, 227 ( 1st Ci r . 2012) ; t o t he

    ext ent t hat t hei r cl ai ms chal l enge t he suf f i ci ency of t he

    government ' s evi dence, we agai n empl oy de novo r evi ew, appr ai si ng

    t he pr oof i n t he l i ght most f avor abl e t o t he ver di ct , Uni t ed St at es

    v. Rodr guez- Vl ez, 597 F. 3d 32, 38 ( 1st Ci r . 2010) .

    A. Agents

    Sect i on 666 r equi r es t he government t o show t hat t he

    i ndi vi dual r ecei vi ng or sol i ci t i ng t he br i be was "an agent of an

    or gani zat i on, or of a St at e, l ocal , or I ndi an t r i bal gover nment , or

    any agency t her eof . " 18 U. S. C. 666( a) ( 1) . The t er m "agent " i s

    def i ned as " a per son aut hor i zed t o act on behal f of anot her per son

    or a government and, i n t he case of an organi zat i on or government ,

    i ncl udes a ser vant or empl oyee, and a par t ner , di r ect or , of f i cer ,

    manager , and r epr esent at i ve. " I d. 666( d) ( 1) . Def endant Mar t nez

    mai nt ai ns t hat he coul d not be convi ct ed under 666( a) ( 1) ( B)

    because he was not an agent of t he Commonweal t h of Puer t o Ri co.

    Def endant Br avo ar gues t hat because nei t her Mar t nez nor de Cast r o

    Font were agents of t he Commonweal t h, he cannot be gui l t y of

    br i bi ng t hem pur suant t o 666( a) ( 2) .

    1. The Scope of the Agency

    At t he out set , we r ej ect any not i on t hat st at e

    l egi sl at or s ar e cat egor i cal l y exempt f r ompr osecut i on under 666.

    I ndeed, t he pl ai n l anguage of t he st at ut e i ncl udes a

    "r epr esent at i ve" of a "gover nment " i n t he l i st of posi t i ons t hat

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    f al l under t he st at ut e' s def i ni t i on of "agent , " 18 U. S. C.

    666( d) ( 1) , and t her e i s no mor e cl assi c gover nment " r epr esent at i ve"

    t han a l egi sl at i ve br anch of f i cer . See Uni t ed St at es v. Li pscomb,

    299 F. 3d 303, 333 ( 5t h Ci r . 2002) ( "Congr ess cl ear l y sought t o

    appl y 666 t o l egi sl at i ve- br anch of f i ci al s. ") ; Uni t ed St at es v.

    Suni a, 643 F. Supp. 2d 51, 67 ( D. D. C. 2009) ( acknowl edgi ng t hat "a

    l egi sl at or who mi suses hi s l egi sl at i ve aut hor i t y t o f aci l i t at e

    cor r upt pr act i ces af f ect i ng agency pr ogr ams t hat r ecei ve f eder al

    f unds may wel l f al l wi t hi n t he ambi t of 666") .

    Def endant s' mor e nuanced ar gument i s t hat t he government

    f ai l ed t o suf f i ci ent l y speci f y t he ent i t y f or whi ch Mar t nez and de

    Cast r o Font were agent s. They mai nt ai n t hat Mar t nez may onl y be

    appr opr i at el y cl assi f i ed as a r epr esent at i ve ( and t hus an agent ) of

    t he Puer t o Ri co Senat e, and not - - as t he i ndi ct ment al l eged - - of

    t he Commonweal t h as a whol e. Thi s di st i nct i on i s si gni f i cant ,

    Def endant s cl ai m, because t he Puer t o Ri co Senate i t sel f had no

    connect i on wi t h, or cont r ol over , t he f eder al f unds i dent i f i ed by

    t he t wo government wi t nesses, and wi t hout such a connect i on t he

    government cannot show t hat " t he organi zat i on, government , or

    agency r ecei ves, i n any one year per i od, benef i t s i n excess of

    $10, 000 under a Feder al pr ogr am. " 18 U. S. C. 666( b) . I f t he

    $10, 000 t hr eshol d i s not met , t hen t he act i ons of t he agent s of t he

    non- qual i f yi ng or gani zat i on, gover nment , or agency - - or t he

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    act i ons of ot her s wi t h r espect t o t hose agent s - - cannot i mpl i cat e

    666.

    Once agai n we need go no f ur t her t han t he pl ai n l anguage

    of t he st atut e t o concl ude that Mar t nez and de Cast r o Font may be

    pr oper l y consi der ed "agent s" of t he Commonweal t h of Puer t o Ri co.

    Among t he f i ve t ypes of ent i t i es f or whi ch one may be an agent

    wi t hi n t he meani ng of 666 i s a st at e government . 5 See 18 U. S. C.

    666( a) ( 1) , ( 2) ( r ef er r i ng t o "an agent of an or gani zat i on, or of

    a St at e, l ocal , or I ndi an t r i bal gover nment , or any agency

    t her eof ") . The Puer t o Ri co Senat e i s a const i t uent par t of t he

    Commonweal t h government , cr eat ed by t he Puer t o Ri co Const i t ut i on.

    See P. R. Const . ar t . I I I , 1. I t s member s ar e t hus par t of t he

    l i mi t ed cat egor y of gover nment of f i ci al s who r epr esent t he "St at e"

    as a whol e, unl i ke empl oyees of l ocal i t i es or of agenci es at ever y

    l evel of gover nment . As such, t hey easi l y f al l wi t hi n t he concept

    of "an agent of . . . a St at e . . . gover nment . " Mar t nez and de

    Cast r o Font wer e t hus pr oper l y consi der ed agent s of t he

    Commonweal t h of Puer t o Ri co under 666.

    At t r i al , t he Associ at e Di r ect or f or t he Of f i ce of Budget

    and Management t est i f i ed t hat dur i ng 2005 - - t he year of t he

    5 Under 666, t he def i ni t i on of "Stat e" i ncl udes " a St at e oft he Uni t ed St ates, t he Di st r i ct of Col umbi a, and any commonweal t h,t er r i t or y, or possessi on of t he Uni t ed St at es. " 18 U. S. C. 666( d) ( 4) ( emphasi s added) . Because "St at e" i s a t er m of ar t i n 666, we shal l r ef er t o Mar t nez and de Cast r o Font as "St at esenat or s. "

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    charged conduct - - t he Commonweal t h r ecei ved over $4. 7 bi l l i on i n

    f eder al f unds. Because Mar t nez and de Cast r o Font are agent s of

    t he Commonweal t h, t he evi dence was suf f i ci ent t o show t hat t hey are

    agent s of a "gover nment . . . [ t hat ] r ecei ves, i n any one year

    per i od, benef i t s i n excess of $10, 000 under a Feder al pr ogr am. " 18

    U. S. C. 666( b) .

    2. Agent Control of Expenditures

    Def endants ar gue t hat bei ng an "agent " under 666 must

    i ncl ude an el ement beyond mer el y r epr esent i ng t he ent i t y. Fr ami ng

    t hei r ar gument par t i al l y i n const i t ut i onal t er ms, t hey asser t t hat ,

    t o est abl i sh t he r equi si t e l i nk t o Congr ess' s aut hor i t y t o

    l egi sl ate under t he Necessary and Proper Cl ause, an "agent " under

    666 "must be ' aut hor i zed t o act on behal f of [ t he ent i t y] wi t h

    r espect t o i t s f unds. ' " Uni t ed St at es v. Whi t f i el d, 590 F. 3d 325,

    344 ( 5t h Ci r . 2009) ( quot i ng Uni t ed St at es v. Phi l l i ps, 219 F. 3d

    404, 411 ( 5t h Ci r . 2000) ) ; see al so Sabr i v. Uni t ed St at es, 541

    U. S. 600, 605 ( 2004) ( descr i bi ng Congr ess' s aut hor i t y under t he

    Necessary and Proper Cl ause) . Def endant s mai nt ai n t hat t he

    gover nment f ai l ed t o adduce any evi dence at t r i al est abl i shi ng t hat

    ei t her Mar t nez or de Cast r o Font , act i ng as senat or s, had t he

    aut hor i t y t o cont r ol t he expendi t ur e of f unds by any ent i t y

    r ecei vi ng f eder al f unds, and t hat t he senat or s t her ef or e do not

    qual i f y as "agent s" f or pur poses of 666.

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    We di sagr ee. Nei t her t he st atut ory l anguage nor

    const i t ut i onal pr i nci pl es l ead t o such a r est r i ct ed under st andi ng

    of t he pr ovi si on. As t he El event h Ci r cui t r ecent l y not ed when

    pr esent ed wi t h thi s ar gument , " [ n] owher e does t he st at ut or y t ext

    ei t her ment i on or i mpl y an addi t i onal qual i f yi ng r equi r ement t hat

    t he per son be aut hor i zed t o act speci f i cal l y wi t h r espect t o t he

    ent i t y' s f unds. " Uni t ed St at es v. Keen, 676 F. 3d 981, 989- 90 ( 11t h

    Ci r . 2012) . The st at ut e mer el y r equi r es that t he i ndi vi dual be

    "aut hor i zed t o act on behal f of anot her per son or gover nment . " 18

    U. S. C. 666( d) ( 1) . I n i nt er pr et i ng t he t ext of a st at ut e, "we

    wi l l not depar t f r om, or ot her wi se embel l i sh, t he l anguage of a

    st at ut e absent ei t her undeni abl e t extual ambi gui t y, or some ot her

    ext r aor di nar y consi der at i on, such as t he pr ospect of yi el di ng a

    pat ent l y absur d r esul t . " Pr i t zker v. Yar i , 42 F. 3d 53, 67- 68 ( 1st

    Ci r . 1994) ( ci t at i ons omi t t ed) ; cf . Sal i nas v. Uni t ed St at es, 522

    U. S. 52, 57- 58 ( 1997) . Def endant s f ai l t o show t hat any absur d

    r esul t woul d f ol l ow f r om a r eadi ng l oyal t o t he pl ai n meani ng of

    the statute.

    The Supr eme Cour t ' s and t hi s ci r cui t ' s 666

    j ur i spr udence suppor t t he concl usi on t hat t he st at ut e i ncor porat es

    no embel l i shment on t he concept of "agent . " I ndeed, t he Supr eme

    Cour t has r epeat edl y r ej ect ed const r uct i ons of 666 t hat woul d

    i mpose l i mi t s beyond t hose set out i n the pl ai n meani ng of t he

    st at ut e. I n Sal i nas, f or exampl e, t he Cour t r ej ect ed a def endant ' s

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    at t empt t o r ead i nt o t he st at ut e an ext r a- t extual r equi r ement of

    pr oof t hat " t he br i be i n some way af f ect ed f eder al f unds, f or

    i nst ance by di ver t i ng or mi sappr opr i at i ng t hem, bef or e t he br i be

    vi ol at es 666( a) ( 1) ( B) . " 522 U. S. at 55- 56. I n r eachi ng i t s

    concl usi on, t he Cour t poi nt ed t o the "enact ment ' s expansi ve,

    unqual i f i ed l anguage, bot h as t o t he br i bes f or bi dden and the

    ent i t i es cover ed. " I d. at 56. Seven year s l at er , i n Sabr i v.

    Uni t ed St at es, t he Cour t r ej ect ed a si mi l ar ar gument t hat t he

    st at ut e requi r es proof of a "nexus" bet ween a br i be or ki ckback and

    some f eder al money. I t not ed t hat whi l e "not ever y br i be or

    ki ckback of f er ed or pai d to agent s of gover nment s cover ed by

    666( b) wi l l be t r aceabl y ski mmed f r omspeci f i c f eder al payment s,

    or show up i n t he gui se of a qui d pr o quo f or some der el i ct i on i n

    spendi ng a f eder al gr ant , " t he absence of such l i nks does not

    "por t end[ ] . . . enf or cement beyond t he scope of f eder al i nt er est ,

    f or t he r eason t hat cor r upt i on does not have t o be t hat l i mi t ed t o

    af f ect t he f eder al i nt er est . " 541 U. S. at 605- 06; see al so Fi scher

    v. Uni t ed St at es, 529 U. S. 667, 677- 79 ( 2000) ( adopt i ng br oad

    r eadi ng of "benef i t s" under 666( b) i n l i ght of st at ut or y l anguage

    "r eveal [ i ng] Congr ess' expansi ve, unambi guous i nt ent t o ensur e t he

    i nt egr i t y of or gani zat i ons par t i ci pat i ng i n f eder al assi st ance

    pr ogr ams" ) .

    We pr evi ousl y addr essed t he scope of 666( d) ( 1) ' s

    def i ni t i on of "agent " i n Uni t ed St at es v. Sot omayor - Vzquez, 249

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    F. 3d 1 ( 1st Ci r . 2001) . Dr awi ng l ar gel y f r om t he Supr eme Cour t ' s

    i nt er pr et at i on of t he st at ut e i n Sal i nas, we hel d t hat "an

    expansi ve def i ni t i on of ' agent ' i s necessar y t o f ul f i l l t he pur pose

    of 666, i . e. , t o pr ot ect t he i nt egr i t y of f eder al f unds. " I d. at

    8. I n suppor t of t hi s r eadi ng, we quot ed at l engt h f r om t he

    di ssent i n Uni t ed St at es v. Phi l l i ps:

    [ T] he expansi ve st at ut or y def i ni t i on [ i n 666( d) ( 1) ] r ecogni zes t hat an i ndi vi dual canaf f ect agency f unds despi t e a l ack of power t oaut hor i ze t hei r di r ect di sbur sement .Ther ef or e, t o br oadl y pr ot ect t he i nt egr i t y off eder al f unds gi ven t o an agency, 666appl i es t o any i ndi vi dual who repr esent s t heagency i n any way, as r epr esent i ng or act i ngon behal f of an agency can af f ect i t s f undseven i f t he act i on does not di r ect l y i nvol vef i nanci al di sbur sement .

    I d. at 8 ( quot i ng Phi l l i ps, 219 F. 3d at 422 n. 3 ( Gar za, J . ,

    di ssent i ng) ) . We t hus hel d t hat "an out si de consul t ant wi t h

    si gni f i cant manager i al r esponsi bi l i t y" coul d be an "agent " of a

    gover nment ent i t y. I d.

    I n keepi ng wi t h our own precedent and t hat of t he Supreme

    Cour t , we concl ude t hat embr aci ng an appr oach f ai t hf ul t o t he pl ai n

    l anguage of 666 i s appr opr i at e her e. Even i f t he of f i ci al s

    accept i ng br i bes do not have t he abi l i t y t o cont r ol t he expendi t ur e

    of an ent i t y' s f unds, "i t cannot be deni ed t hat t hei r f r audul ent

    conduct poses a t hr eat t o t he i nt egr i t y of t he ent i t y, whi ch i n

    t ur n poses a t hr eat t o t he f eder al f unds ent r ust ed t o t hat ent i t y. "

    Keen, 676 F. 3d at 990; see al so Uni t ed St ates v. Hi nes, 541 F. 3d

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    833, 835- 36 ( 8t h Ci r . 2008) . Such conduct " r ai se[ s] t he r i sk

    [ t hat ] par t i ci pat i ng or gani zat i ons wi l l l ack t he r esour ces

    r equi si t e t o pr ovi de t he l evel and qual i t y of car e envi si oned by

    t he pr ogr am. " Fi scher , 529 U. S. at 681- 82; cf . Sabr i , 541 U. S. at

    606 ( "Money i s f ungi bl e, br i bed of f i ci al s ar e unt r ust wor t hy

    st ewar ds of f eder al f unds, and cor r upt cont r act or s do not del i ver

    dol l ar - f or - dol l ar val ue. ") . Nar r owi ng t he scope of 666( d) ( 1) ' s

    def i ni t i on of "agent " woul d be "i nconsi st ent not onl y wi t h t he

    expansi ve, unqual i f i ed l anguage t hat Congr ess has el ect ed to use,

    but al so wi t h Congr ess' cl ear obj ect i ve of ensur i ng t he i nt egr i t y

    of ent i t i es r ecei vi ng subst ant i al sums of f eder al f unds. " Keen,

    676 F. 3d at 991 ( ci t at i on omi t t ed) ( i nt er nal quot at i on mar ks

    omi t t ed) . We t her ef or e decl i ne t o do so.

    These concer ns about f i nanci al i nt egr i t y al so doom

    Def endant s' const i t ut i onal ar gument . " [ I ] n det er mi ni ng whet her t he

    Necessar y and Pr oper Cl ause gr ant s Congr ess t he l egi sl at i ve

    aut hor i t y t o enact a par t i cul ar f eder al st at ut e, we l ook t o see

    whet her t he st at ut e const i t ut es a means t hat i s r at i onal l y rel at ed

    t o t he i mpl ement at i on of a const i t ut i onal l y enumer at ed power . "

    Uni t ed St at es v. Comst ock, 130 S. Ct . 1949, 1956 ( 2010) . I n

    r ej ect i ng a di f f er ent Necessary and Pr oper Cl ause chal l enge t o

    666 i n Sabr i , 6 t he Supreme Cour t wr ot e:

    6 The def endant i n Sabr i argued that 666 coul d not beconst i t ut i onal l y appl i ed "because i t f ai l s t o r equi r e pr oof of anyconnect i on between a br i be or ki ckback and some f ederal money. "

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    Congr ess has aut hor i t y under t he Spendi ngCl ause t o appr opr i ate f eder al moneys t opr omot e t he gener al wel f ar e, Ar t . I , 8, cl .1, and i t has cor r espondi ng aut hor i t y undert he Necessar y and Proper Cl ause . . . t o seet o i t t hat t axpayer dol l ar s appr opr i at ed under

    t hat power are i n f act spent f or t he gener alwel f ar e, and not f r i t t er ed away i n gr af t or onproj ect s under mi ned when f unds ar e si phonedof f or cor r upt publ i c of f i cer s ar e der el i ctabout demandi ng val ue f or dol l ars.

    541 U. S. at 605.

    We have no hesi t at i on i n concl udi ng t hat "measur es t o

    pol i ce t he i nt egr i t y of ent i t i es r ecei vi ng f eder al f unds f al l under

    t he scope of t hi s power , " Keen, 676 F. 3d at 991, even absent

    evi dence of an agent ' s aut hor i t y t o act speci f i cal l y wi t h r espect

    t o t he cover ed ent i t y' s f unds. "Congr ess does not have t o si t by

    and accept t he r i sk of oper at i ons t hwar t ed by l ocal and st at e

    i mpr obi t y. " Sabr i , 541 U. S. at 605. To accept t hat t her e can onl y

    be harmf ul ef f ect s of such di shonest conduct when t he act or has

    aut hor i t y t o cont r ol t he expendi t ur e of t he ent i t y' s f unds woul d be

    nai ve; t o accept t hat t he pr ohi bi t i on of such conduct by such

    i ndi vi dual s i s not "r at i onal l y rel at ed" t o Congr ess' i mpl ement at i on

    of i t s const i t ut i onal l y enumer at ed power s woul d be an undul y

    r est r i ct i ve appl i cat i on of t hat st andar d. The Supr eme Cour t has

    st at ed t hat t o f al l wi t hi n t he scope of t he f eder al i nt er est , "[ i ] t

    i s cer t ai nl y enough t hat t he st at ut es condi t i on t he of f ense on a

    t hr eshol d amount of f eder al dol l ar s def i ni ng t he f eder al i nt er est ,

    541 U. S. at 604.

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    such as t hat provi ded [ i n 666] . " I d. at 606. We see no basi s

    f or depar t i ng f r om t hat vi ew her e.

    B. The Transactional Element

    For a br i be t o f al l wi t hi n t he pur vi ew of 666, i t must

    be made " i n connect i on wi t h any busi ness, t r ansact i on, or ser i es of

    t r ansact i ons of [ t he cover ed] or gani zat i on, gover nment , or agency

    i nvol vi ng anythi ng of val ue of $5, 000 or mor e. " 18 U. S. C.

    666( a) ( 1) ( B) , ( a) ( 2) . Thi s r equi r ement has been r ef er r ed t o as

    t he " t r ansact i onal el ement " of 666. Uni t ed St at es v. Robi nson,

    663 F. 3d 265, 270 ( 7t h Ci r . 2011) . Def endant s poi nt out t hat a

    ci r cui t spl i t exi st s as t o how t he $5, 000 t hr eshol d i n t he

    t r ansact i onal el ement i s met , but ar gue t hat under ei t her appr oach

    t he gover nment ' s evi dence was i nsuf f i ci ent . Taki ng t hi s

    oppor t uni t y to cl ar i f y the cor r ect st andar d, we concl ude t hat under

    t he pr oper appr oach t he evi dence was suf f i ci ent t o sat i sf y t he

    $5, 000 t hr eshol d and t he t r ansact i onal el ement gener al l y.

    1. Value of Bribe or Transaction?

    I n det er mi ni ng how t o cal cul ate the $5, 000 r equi r ement ,

    some cour t s have suggest ed that a cour t shoul d l ook t o t he val ue of

    t he br i be act ual l y of f er ed or pai d. See Uni t ed St at es v. Abbey,

    560 F. 3d 513, 521 ( 6t h Ci r . 2009) ( st at i ng t hat " 666 cont ai ns

    . . . a r equi r ement t hat t he i l l egal gi f t or br i be be wor t h over

    $5, 000") ; Uni t ed St ates v. Spano, 401 F. 3d 837, 839 ( 7t h Ci r . 2005)

    ( " [ T]o est abl i sh a case under 666, t he gover nment need onl y pr ove

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    t hat an agent . . . was of f er ed or accept ed a br i be wor t h $5000 or

    mor e . . . . " ) ; Uni t ed St at es v. LaHue, 170 F. 3d 1026, 1028 ( 10t h

    Ci r . 1999) ( st at i ng t hat 666 "prohi bi t s t he unl awf ul accept ance

    of anythi ng of val ue of $5, 000 or mor e" ) . Ot her cour t s, however ,

    have hel d t hat t he $5, 000 r equi r ement " r ef er s t o t he val ue of t he

    ' busi ness, t r ansacti on, or ser i es of t r ansacti ons, ' not t he val ue

    of t he br i be. " Uni t ed St at es v. McNai r , 605 F. 3d 1152, 1185 n. 38

    ( 11t h Ci r . 2010) ; see al so Uni t ed St at es v. Duval l , 846 F. 2d 966,

    976 ( 5t h Ci r . 1988) ( "[ I ] t i s cl ear t hat t he $5000 f i gur e qual i f i es

    t he t r ansact i ons or ser i es of t r ansact i ons t hat t he r eci pi ent of

    t he br i be car r i es out i n exchange f or r ecei vi ng ' anyt hi ng of

    val ue. ' " ) .

    I n our vi ew, t he st atut ory l anguage i s unambi guous and

    pl ai nl y r equi r es t he l at t er r eadi ng. Appl i ed t o t he pr esent case,

    666( a) ( 1) ( B) pr ohi bi t s a gover nment agent f r om accept i ng or

    agr eei ng t o accept "anyt hi ng of val ue" f r om anot her i ndi vi dual

    " i nt endi ng t o be i nf l uenced or r ewar ded i n connect i on wi t h any

    busi ness, t r ansact i on, or ser i es of t r ansact i ons" of t hat

    gover nment " i nvol vi ng anyt hi ng of val ue of $5, 000 or more. " 18

    U. S. C. 666( a) ( 1) ( B) ( emphasi s added) . Sect i on 666( a) ( 2)

    pr ohi bi t s of f er i ng, gi vi ng, or agr eei ng t o gi ve "anyt hi ng of val ue"

    t o an i ndi vi dual wi t h t he "i nt ent t o i nf l uence or r ewar d" a

    gover nment agent " i n connect i on wi t h any busi ness, t r ansact i on, or

    ser i es of t r ansact i ons" of t hat gover nment " i nvol vi ng anyt hi ng of

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    val ue of $5, 000 or mor e. " I d. 666( a) ( 2) ( emphasi s added) . The

    t hi ng accept ed or agr eed t o be accept ed i n 666( a) ( 1) ( B) - - and

    t he t hi ng gi ven or of f er ed i n 666( a) ( 2) - - i s t he br i be. Thus,

    t he br i be can be "anythi ng of val ue" - - i t need not be wor t h

    $5, 000. The $5, 000 el ement i nst ead r ef er s t o t he val ue of t he

    "busi ness" or " t r ansact i on" sought t o be i nf l uenced by t he br i be.

    " I n ot her wor ds, t he subj ect mat t er of t he br i be must be val ued at

    $5, 000 or mor e; t he br i be i t sel f need onl y be ' anyt hi ng of val ue. ' "

    Robi nson, 663 F. 3d at 271.

    We not e, however , t hat t he val ue of t he br i be may be

    r el evant i n det er mi ni ng t he val ue of t he br i be' s obj ect i ve. I n

    Uni t ed St at es v. Mar mol ej o, 89 F. 3d 1185 ( 5t h Ci r . 1996) , f or

    exampl e, t he cour t l ooked t o t he val ue of br i bes wher e t he subj ect

    mat t er of t he br i bes consi st ed of "i nt angi bl e i t ems. " The

    def endant s i n Marmol ej o wer e t wo l ocal l aw enf orcement of f i cer s who

    had agr eed t o per mi t conj ugal vi si t s bet ween an i nmate and hi s wi f e

    ( and hi s gi r l f r i end) i n exchange f or a mont hl y payment of $6, 000

    and $1, 000 per conj ugal vi si t . I d. at 1191. The cour t not ed t hat

    "[ t ] he t r ansact i ons i nvol ved somet hi ng of val ue - - conj ugal vi si t s

    t hat [ t he pr i soner ] was wi l l i ng t o pay f or , " i d. at 1193 - - and i t

    l ooked t o " t r adi t i onal val uat i on met hods" t o est i mat e t hat val ue,

    i d. at 1194. The cour t concl uded t hat t he pr i soner ' s wi l l i ngness

    t o pay $6, 000 per mont h pl us $1, 000 per vi si t set t he market val ue

    f or t he conj ugal vi si t s, and i t t hus f ound t hat t he t r ansact i ons

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    between t he pr i soner and the t wo def endant s " i nvol ved somethi ng of

    val ue of $5, 000 or mor e. " I d. at 1194 ( i nt er nal quotat i on mar ks

    omi t t ed) .

    Hence, wher e t he subj ect mat t er of t he br i be i s a "t hi ng

    of val ue" wi t hout a f i xed pr i ce, cour t s may l ook t o the val ue of

    t he br i be as evi dence of t he val ue of t he "busi ness, t r ansact i on,

    or ser i es of t r ansact i ons. " That col l at er al use does not al t er t he

    pr oposi t i on t hat t he br i be i t sel f need onl y consi st of "anyt hi ng of

    val ue. "

    2. "Business or transaction" requirement

    Def endant s mai nt ai n that t he enactment of Senate Pr oj ect s

    410 and 471 shoul d not be consi dered t o be "i n connect i on wi t h any

    busi ness, t r ansacti on, or ser i es of t r ansacti ons . . . i nvol vi ng

    anyt hi ng of val ue of $5, 000 or more" under 666. They of f er

    sever al j ust i f i cat i ons f or t hi s posi t i on. We f i nd none of t hem

    per suasi ve.

    Fi r st , Def endant s f ocus on t he " i n connect i on wi t h"

    l anguage. Thei r at t ack i s anchor ed i n a Fi f t h Ci r cui t case, Uni t ed

    St at es v. Whi t f i el d, whi ch i nvol ved t wo st at e j udges who wer e

    convi ct ed of accept i ng br i bes f r om an at t or ney i n exchange f or

    f avorabl e r ul i ngs i n hi s cases. 590 F. 3d at 335. The gover nment

    argued, and t he cour t assumed, t hat t he j udges wer e "agent s" of t he

    Admi ni st r at i ve Of f i ce of t he Cour t s ( "AOC") , a Mi ssi ssi ppi st at e

    agency t hat r ecei ved over $10, 000 i n f ederal f unds and was "char ged

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    wi t h assi st [ i ng] i n t he ef f i ci ent admi ni st r at i on of t he nonj udi ci al

    busi ness of t he cour t s of t he st at e. " I d. at 344 ( emphasi s added)

    ( ci t at i on omi t t ed) ( i nt er nal quot at i on mar ks omi t t ed) . The cour t

    hel d, however , t hat t he j udges' r ul i ngs wer e not made " i n

    connect i on wi t h" t he busi ness or t r ansact i ons of t he AOC, as t hey

    wer e made whi l e the j udges wer e per f or mi ng pur el y j udi ci al dut i es.

    I d. at 346- 47. Her e, Def endant s mai nt ai n t hat t he f eder al f unds

    i dent i f i ed by t he government went t o the Puer t o Ri co Depar t ment s of

    Educat i on and Tr easur y, and because t here i s no nexus between t he

    Depar t ment s of Educat i on and Tr easur y and t he act of l egi sl at i ng

    Senate Pr oj ect s 410 and 471 i n t he Puer t o Ri co Senate, t he

    l egi sl at i on was not " i n connect i on wi t h" t he busi ness or

    t r ansact i ons of t he f eder al l y f unded ent i t y.

    What ever t he mer i t s of Whi t f i el d' s " nexus" r equi r ement ,

    t hey ar e not i mpl i cated i n t hi s case, as we have deter mi ned t hat

    Mar t nez and de Cast r o Font wer e agent s of t he Commonweal t h of

    Puer t o Ri co, whi ch r ecei ves f eder al f unds. When t he j udges i n

    Whi t f i el d wer e act i ng i n t hei r capaci t y as j udi ci al deci si onmaker s,

    t hey wer e not act i ng wi t hi n t hei r scope as agent s of t he AOC, as

    t he AOC was speci f i cal l y l i mi t ed t o t he nonj udi ci al busi ness of t he

    cour t s. By cont r ast , when Mar t nez and de Cast r o Font wer e act i ng

    i n t hei r capaci t y as l egi sl at or s, t hey wer e per f or mi ng t he pr eci se

    f unct i ons t hat member s of a st at e l egi sl at i ve body per f or m as

    agent s of a st at e gover nment . The l egi sl at i ve act s t hat

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    const i t ut ed t he subj ect of t he br i bes had a di r ect "connect i on wi t h

    t he busi ness, t r ansact i on, or ser i es of t r ansact i ons" of t he

    Commonweal t h of Puer t o Ri co.

    Second, Def endant s argue t hat t he passi ng of Senat e

    l egi sl at i on cannot be consi der ed "busi ness" or a "t r ansact i on"

    under 666. The t hr ust of t hei r ar gument i s t hat t he t er ms

    "busi ness" and " t r ansact i on" shoul d be const r ued nar r owl y t o

    encompass onl y commer ci al conduct , and "t he Senat e does not conduct

    busi ness or f i nanci al t r ansact i ons thr ough l egi sl at i ng. "

    I n Sal i nas, t he Supr eme Cour t r ej ect ed a def endant ' s

    si mi l ar at t empt t o i mpose a nar r owi ng const r uct i on on 666. 522

    U. S. at 57. Ther e, t he def endant ar gued t hat f eder al f unds must be

    af f ect ed t o vi ol at e 666( a) ( 1) ( B) . I d. at 56. Looki ng t o t he

    l anguage of t he st at ut e, t he Cour t concl uded t hat t he wor d "any, "

    whi ch pr ecedes t he busi ness or t r ansact i on cl ause, under cut s t he

    at t empt t o i mpose t he def endant ' s nar r ow i nt er pr et at i on. I d. at

    56- 57. The Cour t ' s emphasi s on t he expansi ve l anguage i n

    666( a) ( 1) ( B) i n Sal i nas suggest s t hat t he cour t s shoul d avoi d

    i mposi ng nar r owi ng const r uct i ons on t hat l anguage. Fur t her more,

    such a r eadi ng woul d f or ecl ose l ar ge swat hs of gover nment act i vi t y

    t hat , t hough t echni cal l y "non- commer ci al , " coul d be pr of i t abl e f or

    unscr upul ous i ndi vi dual s t o at t empt t o i nf l uence. Thi s nar r ow

    const r uct i on woul d be cont r ar y t o Congr ess' s i nt ent . See i d. at 56

    ( ci t i ng 666' s " expansi ve, unqual i f i ed l anguage, bot h as t o t he

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    br i bes f or bi dden and t he ent i t i es cover ed, " as evi dence of

    l egi sl at i ve i nt ent t o const r ue st at ut e br oadl y) . Recent l y

    conf r ont i ng t hi s argument , t he Sevent h Ci r cui t st at ed:

    The "busi ness" of a f eder al l y f unded"or gani zat i on, gover nment , or agency" i s notcommonl y "busi ness" i n t he commerci al sense oft he wor d. An i nt er pr et at i on t hat nar r owl yl i mi t s t he scope of t he t r ansact i onal el ementt o busi ness or t r ansact i ons t hat ar ecommer ci al i n nat ur e woul d have t he ef f ect ofexcl udi ng br i bes pai d t o i nf l uence agent s ofst at e and l ocal gover nment s. Thi s cont r adi ct st he expr ess st at ut or y t ext .

    Robi nson, 663 F. 3d at 274; see al so Marmol ej o, 89 F. 3d at 1191- 92.

    We agr ee, and hol d that t he busi ness or t r ansact i on cl ause i n 666

    does not l i mi t t he st at ut e' s r each t o pur el y commer ci al conduct .

    Thi r d, Def endant s f ocus on t he wor d " i nvol vi ng, " 7 and

    posi t t hat i n or der t o sat i sf y 666, t he pr of i t t hat Ranger

    Amer i can woul d st and t o gai n f r om t he passage of t he Senate

    Proj ect s woul d "have t o have been a par t of or a necessary

    consequence of t he l egi sl at i on or have been i ncl uded i n i t s scope

    t o sat i sf y t he $5, 000 r equi r ement . " Because t he l egi sl at i on i t sel f

    was " r evenue- neut r al " and gave nothi ng di r ect l y t o Ranger Amer i can,

    Def endant s mai nt ai n t hat nei t her of t he Senat e Pr oj ect s " i nvol ved"

    7 See 18 U. S. C. 666( a) ( 1) ( B) ( pr ohi bi t i ng an agent f r om,i nt er al i a, accept i ng or agr eei ng t o accept anyt hi ng of val ue" i nt endi ng t o be i nf l uenced or r ewar ded i n connect i on wi t h anybusi ness, t r ansact i on, or ser i es of t r ansact i ons of suchor gani zat i on, gover nment , or agency i nvol vi ng anythi ng of val ue of$5, 000 or more") ( emphasi s added) .

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    pr ospect i ve r evenues f or Ranger Amer i can ( and, by ext ensi on,

    Br avo) .

    We f i nd no suppor t i n t he case l aw or t he st at ut or y

    l anguage f or t hi s unnecessar i l y r est r i ct i ve i nt er pr et at i on of

    666. Even i f l egi sl at i on i s r evenue- neut r al on i t s f ace, i t i s

    suf f i ci ent i f t he di r ect and f or eseeabl e ef f ect of t hat l egi sl at i on

    woul d be t o gi ve t he i ndi vi dual of f er i ng t he br i be a par t i cul ar

    desi r ed r esul t - - assumi ng, of cour se, t hat t he t r ansact i on

    i nvol ved somet hi ng of val ue of $5, 000 or more. Her e, t he

    gover nment pr esent ed evi dence t hat t he f oreseeabl e ef f ect of t he

    passage of Senat e Pr oj ect 471 woul d be a change i n the ar mor ed car

    ser vi ce i ndust r y, whi ch i n t ur n woul d r esul t i n f i nanci al benef i t s

    t o Ranger Amer i can and Br avo f ar exceedi ng $5, 000. Thi s i mpact i s

    suf f i ci ent t o sat i sf y the "i nvol vi ng" r equi r ement of 666. 8

    3. Sufficiency of the Evidence

    Wi t h t he appr opr i at e under st andi ng of t he st at ut e i n

    mi nd, we can easi l y rej ect Def endant s' suf f i ci ency chal l enge as t o

    t he $5, 000 r equi r ement . Mi guel Por t i l l a, t he pr esi dent of Capi t ol

    8 For t he r easons di scussed above, we al so r ej ect Def endant s'cl ai mt hat i t woul d somehow vi ol ate t he Due Pr ocess Cl ause t o appl y 666 t o st at e senat or s who r ecei ve br i bes i n connect i on wi t h

    l egi sl at i on pendi ng bef or e t hem. Such pr osecut i ons f al l squar el ywi t hi n t he pl ai n t er ms of 666. See Uni t ed St at es v. Counci l man,418 F. 3d 67, 84- 85 ( 1st Ci r . 2005) ( r ej ect i ng def endant ' s ar gumentt hat cour t engaged i n "unf or eseeabl y expansi ve i nt er pr et at i on" ofcri mi nal st at ut e, as act s al l eged const i t ut e "' conduct t hat . . .t he st at ut e . . . has f ai r l y di scl osed t o be wi t hi n i t s scope. ' "( quot i ng Uni t ed St at es v. Lani er , 520 U. S. 259, 266 ( 1997) ) ) .

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    Secur i t y - - a company wi t h whi ch Ranger Amer i can compet ed - -

    t est i f i ed t hat Senate Pr oj ect 471, whi ch sought t o amend Law 108, 9

    woul d have f or ced Ranger Amer i can' s onl y compet i t or s i n t he armored

    car pr ot ect i on busi ness t o cl ose down, t her eby ensur i ng t hat Ranger

    Amer i can woul d have an ef f ect i ve monopol y on t hat sect or of t he

    secur i t y i ndust r y i n Puer t o Ri co. Nest or Medi na, t he f or mer

    gener al manager of Loomi s Puer t o Ri co - - a subsi di ary of Loomi s

    U. S. , an ar mor ed car ser vi ce - - t est i f i ed t hat Loomi s cont r ol l ed

    r oughl y 35% of t he ar mor ed car servi ce i ndust r y, Ranger Amer i can

    52%, and Br i nks t he r emai nder . Medi na st at ed t hat Loomi s Puer t o

    Ri co net t ed $1. 5 mi l l i on i n pr of i t s i n 2005, and t hat t her e woul d

    t her ef or e be an ext r a $1. 5 mi l l i on i n addi t i onal pr of i t s avai l abl e

    f or ot her armored car compani es t o capt ur e i f Loomi s wer e to l eave

    t he mar ket . 10 Because, accor di ng t o Por t i l l a' s t est i mony, Ranger

    Amer i can woul d have been t he onl y company l ef t i n that market , i t

    9 Por t i l l a t est i f i ed t hat Law 108 r egul at es t he l i censi ng ofsecur i t y agenci es i n Puer t o Ri co.

    10 Def endant s t ake i ssue wi t h cer t ai n of t he di st r i ct cour t ' sevi dent i ary r ul i ngs as t o Medi na' s t est i mony. These ar gument s donot af f ect our suf f i ci ency anal ysi s f or t wo r easons. Fi r st ,Def endant s woul d have suf f er ed no pr ej udi ce by t hi s t est i mony.Por t i l l a' s t est i mony - - whi ch i s not chal l enged by Def endant s - -al one pr ovi des suf f i ci ent evi dence on t hi s i ssue. Any er r or wi t hr espect t o t he admi ssi on of Medi na' s t est i mony woul d t her ef ore be

    har ml ess. Second, r evi ewi ng t he di st r i ct cour t ' s evi dent i ar yr ul i ngs under t he pr oper st andar d, see Uni t ed St at es v. Appol on,695 F. 3d 44, 60 ( 1st Ci r . 2012) , we cannot say t hat t he di st r i ctcour t abused i t s di scr et i on i n per mi t t i ng Medi na t o t est i f y onr edi r ect about hi s vi ews r egar di ng Senat e Pr oj ect 471 and i t spot ent i al i mpact on Loomi s, nor i n i t s deci si on denyi ng r ecr oss ofMedi na.

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    i s r easonabl e to concl ude t hat Br avo' s company woul d st and to

    capt ur e a subst ant i al por t i on of t hat pr of i t . Thi s t est i mony

    pr ovi ded suf f i ci ent evi dence f or a r easonabl e j ur y t o concl ude t hat

    Senat e Pr oj ect 471 was wor t h $5, 000 or mor e t o Br avo.

    III.

    Def endant s chal l enge t he di st r i ct cour t ' s j ur y

    i nst r uct i ons as t o t he 666 count s on sever al gr ounds. We need

    r each onl y Def endant s' cont ent i on t hat t he cour t ' s i nst r uct i ons,

    r ei nf or ced by t he gover nment ' s cl osi ng ar gument , per mi t t ed t he j ur y

    t o f i nd t hem gui l t y of of f er i ng and r ecei vi ng a gr at ui t y, r at her

    t han a br i be. Thi s cl ai mnecessar i l y encompasses t he ar gument t hat

    666 does not i n f act cr i mi nal i ze gr at ui t i es, a quest i on of f i r st

    i mpr essi on i n t hi s ci r cui t and an i ssue t hat has gener at ed

    consi der abl e debat e i n the cour t s and among comment at or s.

    "We revi ew de novo pr eserved cl ai ms of l egal er r or i n

    j ur y i nst r uct i ons, but we r evi ew f or abuse of di scr et i on cl ai med

    er r or s i n i nst r ucti ons' f or m or wor di ng. " Uphof f Fi guer oa v.

    Al ej andr o, 597 F. 3d 423, 434 ( 1st Ci r . 2010) . I n our r evi ew, "we

    l ook t o t he chal l enged i nst r uct i ons i n r el at i on t o t he char ge as a

    whol e, aski ng whet her t he char ge i n i t s ent i r et y - - and i n t he

    cont ext of t he evi dence - - pr esent ed t he r el evant i ssues t o the

    j ur y f ai r l y and adequat el y. " Dr umgol d v. Cal l ahan, 707 F. 3d 28, 53

    ( 1st Ci r . 2013) ( quot i ng Sony BMG Musi c Ent m' t v. Tenenbaum, 660

    F. 3d 487, 503 ( 1st Ci r . 2011) ) ( i nt er nal quot at i on mar ks omi t t ed) .

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    Even i f we f i nd t hat a cour t ' s i nst r uct i ons wer e er r oneous, we wi l l

    vacat e onl y i f we det er mi ne t hat t he er r or was prej udi ci al "based

    on a r evi ew of t he r ecord as a whol e. " Mass. Eye & Ear I nf i r mary

    v. QLT Phot ot her apeut i cs, I nc. , 552 F. 3d 47, 72 ( 1st Ci r . 2009) .

    We begi n by r evi ewi ng t he i nst r uct i ons. Because we agr ee

    t hat t hey al l owed a gr at ui t i es t heor y of gui l t , we t hen consi der

    t he scope of 666.

    A. The Instructions

    1. Background

    Three of t he di st r i ct cour t ' s t hi r t y- si x j ur y

    i nst r ucti ons ar e r el evant her e. The f i r st i s J ur y I nst r ucti on 20,

    t i t l ed "Br i ber y Concer ni ng Pr ogr ams Recei vi ng Feder al Funds, 18

    U. S. C. 666( a) ( 2) . " Thi s i nst r uct i on concer ns Def endant Br avo. I t

    expl ai ns t hat

    Def endant Br avo i s accused of cor r upt l y

    gi vi ng, of f er i ng, or agr eei ng t o gi ve t hi ngsof val ue t o def endant Mar t nez and/ or J or ge deCast r o- Font , wi t h i nt ent t o i nf l uence orr eward def endant Mar t nez and/ or deCast r o- Font i n connect i on wi t h a busi ness,t r ansacti on, or ser i es of t r ansacti ons of t heCommonweal t h of Puer t o Ri co governmenti nvol vi ng more than $5, 000.

    Much of t he l anguage t hat f ol l ows t hi s i nt r oduct i on t r acks t he

    l anguage of t he st at ut e and i s not pr obl emat i c. For i nst ance,

    par agr aphs t wo t hr ough f our of J ur y I nst r uct i on 20 st at e t he

    f ol l owi ng:

    For you t o f i nd def endant Br avo gui l t y ofbr i ber y, you must be convi nced t hat t he

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    Government has proven each of t he f ol l owi ngt hi ngs beyond a r easonabl e doubt :

    Fi r st , t hat def endant Br avo gave,of f er ed, or agr eed t o gi ve any t hi ng of val uet o any per son;

    Second, t hat def endant Br avo di d so

    cor r upt l y wi t h t he i nt ent t o i nf l uence orr ewar d an agent of t he Puer t o Ri co gover nmenti n connect i on wi t h any busi ness, t r ansact i on,or ser i es of t r ansact i ons of t he Puer t o Ri cogover nment . . . .

    Thi s same t ype of st at ut e- t r acki ng l anguage i s f ound i n

    t he second r el evant i nst r ucti on, J ur y I nst r ucti on 21, t i t l ed

    "Br i ber y Concer ni ng Progr ams Recei vi ng Feder al Funds, 18 U. S. C.

    666( a) ( 1) ( B) . " Thi s i nst r uct i on concer ns t he 666 char ges

    agai nst Def endant Mar t nez. Par agr aphs t wo t hr ough f i ve st at e:

    For you t o f i nd def endant Mar t nez gui l t y ofbr i ber y, you must be convi nced t hat t heGovernment has proven each of t he f ol l owi ngt hi ngs beyond a r easonabl e doubt :

    Fi r st , t hat def endant Mar t nez was anagent of t he Commonweal t h of Puer t o Ri cogovernment whose dut i es i ncl uded t hose of anel ect ed Senat or of t he Commonweal t h of Puer t oRi co, as char ged;

    Second, t hat def endant Mar t nezsol i ci t ed, demanded, accept ed or agr eed t oaccept any t hi ng of val ue f r omanot her per son;

    Thi r d, t hat def endant Mar t nez di d socor r upt l y wi t h t he i nt ent t o be i nf l uenced orr ewarded i n connect i on wi t h some busi ness,t r ansact i on or ser i es of t r ansact i ons of t hePuer t o Ri co gover nment . . . .

    However , cer t ai n par t s of t hese t wo i nst r uct i ons i ncl ude

    l anguage t hat does not t r ack t he st atut e. Among t hese are

    par agr aph t en of J ur y I nst r uct i on 20 and par agr aph el even of J ur y

    I nst r uct i on 21. Par agr aph t en st at es:

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    When consi der i ng t he Fi r st and Secondel ement s above, I i nst r uct you t hat adef endant i s not r equi r ed t o have gi ven,of f er ed, or agr eed t o gi ve a thi ng of val uebef or e t he busi ness, t r ansact i on, or ser i es oft r ansact i ons. Rat her , t he Government may

    pr ove t hat def endant Br avo gave, of f er ed, oragr eed t o gi ve t he t hi ng of val ue bef ore,af t er , or at t he same t i me as t he busi ness,t r ansacti on, or ser i es of t r ansacti ons.Ther ef or e, t he government does not need t opr ove t hat def endant Br avo gave, of f er ed, oragr eed t o of f er t he t r i p t o Las Vegas bef or edef endant Mar t nez per f or med any of f i ci alacti on or ser i es of acts.

    ( Emphases added. ) Par agr aph el even of J ur y I nst r uct i on 21 appears

    t o have a pur pose si mi l ar t o that of par agr aph t en of J ur y

    I nst r uct i on 20, t hough par agr aph el even i s concer ned wi t h t he

    t i mi ng of Def endant Mar t nez' s sol i ci t at i on, demand, accept ance, or

    agr eement t o accept t he t hi ng of val ue:

    When consi der i ng t he Second and Thi r del ement s above, I i nst r uct you t hat adef endant i s not r equi r ed t o have accept ed orr ecei ved a t hi ng of val ue bef or e t he busi ness,t r ansacti on, or ser i es of t r ansacti ons.Rat her , t he Gover nment may prove t hatdef endant Mar t nez sol i ci t ed, demanded,accept ed, or agr eed t o accept t he t hi ng ofval ue bef or e, af t er , or at t he same t i me ast he busi ness, t r ansact i on, or ser i es oft r ansact i ons. Ther ef ore, t he Gover nment doesnot need t o pr ove t hat def endant Mar t nezsol i ci t ed, demanded, accept ed or agr eed t oaccept t he t r i p t o Las Vegas bef ore def endantMar t nez per f or med any of f i ci al act or ser i es

    of act s.( Emphases added. )

    The f i nal r el evant i nst r uct i on i s J ur y I nst r uct i on 22,

    t i t l ed si mpl y "Br i ber y. " Thi s i nstr uct i on stat es i n f ul l :

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    I have used t he wor d "br i ber y" i n t hesei nst r ucti ons. Br i ber y r equi r es t hat t hegovernment prove beyond a r easonabl e doubt t heexi st ence of a qui d pr o quo or , i n pl ai nEngl i sh, an agr eement t hat t he t hi ng of val uet hat i s gi ven t o t he publ i c of f i ci al i s i n

    exchange f or t hat publ i c of f i ci al pr omi si ng t oper f orm of f i ci al act s f or the gi ver . I t i snot suf f i ci ent t hat t he t hi ng of val ue i s madet o cur r y f avor because of t he of f i ci al ' sposi t i on or t hat t her e i s some connect i on i nt i me or pl ace wi t h an of f i ci al act t hat i spr omi sed t o t he gi ver ; r ather t her e must be anagr eement t hat t he t hi ng of val ue was of f er edby def endant Br avo and accept ed by Senat orMar t nez i n exchange f or a pr omi se t o per f or man of f i ci al act .

    Def endant s mai nt ai n t hat t he di st r i ct cour t ' s di r ect i ons

    i n J ur y I nst r uct i ons 20 and 21 al l owed t he j ur y t o convi ct Mar t nez

    and Br avo of a gr at ui t y of f ense. They argue t hat a per mi ssi bl e

    const r uct i on of J ur y I nst r uct i on 20 coul d r ead as f ol l ows:

    [ T] he Government may pr ove t hat def endantBr avo . . . of f er ed . . . t he t hi ng of val ue. . . af t er . . . t he busi ness, t r ansact i on,or ser i es of t r ansact i ons. Ther ef or e, t hegovernment does not need t o pr ove t hatdef endant Br avo . . . of f er ed . . . t he t r i pt o Las Vegas bef ore def endant Mar t nezper f or med any of f i ci al act i on or ser i es ofact s.

    Si mi l ar l y, J ur y I nst r uct i on 21 coul d be r ead t o st at e:

    [ T] he Government may pr ove t hat def endantMar t nez . . . agr eed t o accept t he t hi ng ofval ue . . . af t er . . . t he busi ness,

    t r ansacti on, or ser i es of t r ansacti ons.Ther ef or e, t he Gover nment does not need t opr ove t hat def endant Mar t nez . . . agr eed t oaccept t he t r i p t o Las Vegas bef ore def endantMar t nez per f or med any of f i ci al act or ser i esof act s.

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    Def endant s ar gue that i f Br avo had not of f er ed Mar t nez anythi ng

    bef or e Mar t nez per f or med an of f i ci al act , and Mar t nez had

    t her ef or e not accept ed ( or even agr eed t o accept ) anythi ng f r om

    Br avo bef or e per f or mi ng t hat act , any subsequent of f er of a t hi ng

    of val ue f r om Br avo t o Mar t nez cannot be const r ued as a br i be.

    I nst ead, t he of f er woul d mer el y be an of f er of a r ewar d f or an act

    t aken by Mar t nez i n t he past . Thi s, Def endant s mai nt ai n, i s an

    of f er of a gr at ui t y, not a br i be.

    The gover nment does not expl i ci t l y addr ess t hi s

    pot ent i al l y pr obl emat i c const r uct i on of par agr aph t en of J ur y

    I nst r uct i on 20 and par agr aph el even of J ur y I nst r uct i on 21. I t

    ar gues t hat t he t i t l es of t hose i nst r uct i ons - - "Br i ber y Concer ni ng

    Progr ams Recei vi ng Feder al Funds, 18 U. S. C. 666( a) ( 2) " and

    "Br i ber y Concer ni ng Progr ams Recei vi ng Feder al Funds, 18 U. S. C.

    666( a) ( 1) ( B) " - - make cl ear t hat t he j ur y must f i nd br i ber y, not

    a mer e gr at ui t y. Addi t i onal l y, t he gover nment poi nt s t o t he

    unambi guous qui d pr o quo l anguage of J ur y I nst r uct i on 22, whi ch, i t

    cl ai ms, l eaves no doubt t hat t he j ur y was r equi r ed t o f i nd br i ber y

    t o convi ct Def endant s of vi ol at i ng 666.

    Rel at edl y, Def endant s mai nt ai n t hat t he ef f ect of t he

    al l eged er r or s i n J ur y I nst r uct i ons 20 and 21 was magni f i ed by

    cer t ai n st atement s made by t he gover nment dur i ng i t s cl osi ng

    argument . Def endant s poi nt t o t he government ' s st at ement t o t he

    j ur y t hat

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    i t doesn' t mat t er when i t was of f er ed or wheni t was accept ed . . . . These i nst r uct i onscl ar i f y t hat - - t hat i t doesn' t mat t er i f t het r i p was of f er ed bef or e of f i ci al act s wer et aken, at t he same t i me of f i ci al act s wer et aken, or af t er of f i ci al act s wer e t aken,

    because t he cr i me i s of f er i ng or accept i ng t het r i p wi t h i nt ent t o i nf l uence or r ewar d.

    ( Emphasi s added. ) Thi s l anguage, Def endant s posi t , suggest s t hat

    t he government need onl y pr ove a "connect i on" between t he of f i ci al

    act s and t he of f er of t he Las Vegas t r i p, r at her t han a causal

    r el at i onshi p. Def endant s ar gue t hat t he gover nment essent i al l y

    t ol d t he j ur or s t hat t hey coul d convi ct Mar t nez and Br avo of

    vi ol at i ng 666 i f t hey f ound t hat a mer e gr at ui t y - - as opposed t o

    a br i be - - was of f er ed by Br avo and accept ed by Mar t nez.

    2. Analysis

    The Supr eme Cour t expl ai ned t he di st i nct i on between

    br i bes and i l l egal gr at ui t i es i n Uni t ed St at es v. Sun- Di amond

    Gr ower s of Cal i f or ni a, 526 U. S. 398 ( 1999) :The di st i ngui shi ng f eat ur e of each cr i me i si t s i nt ent el ement . Br i ber y r equi r es i nt ent"t o i nf l uence" an of f i ci al act or "t o bei nf l uenced" i n an of f i ci al act , whi l e i l l egalgr at ui t y requi r es onl y that t he gr at ui t y begi ven or accept ed " f or or because of " anof f i ci al act . I n ot her wor ds, f or br i ber yt her e must be a qui d pr o quo - - a speci f i ci nt ent t o gi ve or r ecei ve somet hi ng of val uei n exchange f or an of f i ci al act . An i l l egal

    gr at ui t y, on t he ot her hand, may const i t ut emer el y a r eward f or some f ut ur e act t hat t hepubl i c of f i ci al wi l l t ake ( and may al r eadyhave det er mi ned t o take) , or f or a past actt hat he has al r eady t aken.

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    I d. at 404- 05 ( t hi r d emphasi s added) ( const r ui ng t he gener al

    f eder al br i ber y and gr at ui t y st at ut e, 18 U. S. C. 201) ; see al so

    Uni t ed St ates v. Mar i ano, 983 F. 2d 1150, 1159 ( 1st Ci r . 1993)

    ( not i ng i n a 666 case t hat " [ t ] he essent i al di f f er ence bet ween a

    br i be and an i l l egal gr at ui t y i s t he i nt ent i on of t he br i be- gi ver

    t o ef f ect a qui d pr o quo") . As t he Ei ght h Ci r cui t has not ed,

    " [ t ] he cor e di f f er ence bet ween a br i be and a gr at ui t y i s not t he

    t i me the i l l egal payment i s made, but t he qui d pr o quo, or t he

    agr eement t o exchange [ a t hi ng of val ue] f or of f i ci al act i on. "

    Uni t ed St at es v. Gr i f f i n, 154 F. 3d 762, 764 ( 8t h Ci r . 1998) .

    Al t hough t he t i mi ng of t he payment may not pr ovi de a concl usi ve

    answer as t o whet her t hat payment i s a br i be or a gr at ui t y, t he

    t i mi ng of t he agr eement t o make or r ecei ve a payment may: one

    cannot agr ee t o per f orm an act i n exchange f or payment when t hat

    act has al r eady been per f ormed. Ther ef ore, i f t he agr eement t o

    exchange a t hi ng of val ue f or an act i s made af t er t hat act has

    been per f or med, t hat agr eement cannot be proper l y vi ewed as an

    agr eement t o of f er or accept a br i be.

    Wi t h t hi s di st i nct i on i n mi nd, i t i s cl ear t hat par agr aph

    t en of J ur y I nst r uct i on 20 and par agr aph el even of J ur y I nst r uct i on

    21 t ol d t he j ur y t hat Br avo coul d be convi ct ed under 666 f or

    agr eei ng t o gi ve Mar t nez a gr at ui t y, and t hat Mar t nez coul d be

    convi ct ed under 666 f or agr eei ng t o accept t he same. Par agr aph

    t en expl ai ns t hat f or a convi ct i on under 666, t he gover nment need

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    not pr ove t hat Br avo of f er ed or agr eed to gi ve Mar t nez anythi ng of

    val ue bef or e t he t r ansact i on t hat was t he subj ect of t he "payment "

    t ook pl ace, and t hat i t i s suf f i ci ent f or convi ct i on t o show t hat

    Br avo "of f er ed, or agr eed t o gi ve t he t hi ng of val ue . . . af t er

    . . . t he . . . t r ansacti on. " Si mi l ar l y, par agr aph el even suggest s

    t hat t he government need not prove t hat Mar t nez accept ed or agr eed

    t o accept t he t hi ng of val ue bef ore he per f ormed t he act t hat was

    t he subj ect of t he "payment , " and t hat i t i s suf f i ci ent t o show

    t hat Mar t nez "agr eed t o accept t he t hi ng of val ue . . . af t er

    . . . t he t r ansact i on. "

    Thi s vi ew of t he r equi r ements of 666 was r ei nf or ced by

    t he gover nment ' s cl osi ng ar gument . Li ke t he cour t ' s j ur y

    i nst r uct i ons, si gni f i cant por t i ons of t he gover nment ' s cl osi ng

    argument wer e consi st ent wi t h a br i ber y t heory under 666.

    However , i n emphasi zi ng t hat " i t doesn' t mat t er i f t he t r i p was

    of f er ed . . . af t er of f i ci al act s wer e t aken, " t he gover nment

    i nvi t ed t he j ur y t o f i nd gui l t based on a gr at ui t y t heor y of

    l i abi l i t y.

    Whi l e t he l anguage i n J ur y I nst r uct i on 22 cor r ect l y

    st at es t he r equi r ement s f or a br i ber y convi ct i on, i t was not

    suf f i ci ent t o of f set t he f l at l y cont r ar y l anguage i n J ur y

    I nst r uct i ons 20 and 21. Thi s i s par t i cul ar l y so because t he

    gr at ui t i es t heor y was of f er ed i n t he i nst r uct i ons on t he 666

    count s t hemsel ves, wher eas t he cor r ect br i ber y l anguage was i n a

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    subsequent gl obal i nst r uct i on t hat appl i ed t o bot h t he Puer t o Ri co

    and f eder al br i ber y count s.

    I mpor t ant l y, t he evi dence pr esent ed at t r i al coul d

    suppor t a f i ndi ng t hat t he "payment " Br avo gave and Mar t nez

    r ecei ved const i t ut ed a gr at ui t y. The evi dence showed t hat Mar t nez

    suppor t ed t he Senat e Pr oj ect s af t er t he Las Vegas t r i p - - he vot ed

    i n suppor t of bot h bi l l s wi t hi n a week of r et ur ni ng - - whi ch i s

    consi st ent wi t h a qui d pr o quo, and t her ef or e wi t h a br i ber y

    t heor y. However , he f i r st t ook act i ons i n suppor t of Senat e

    Pr oj ect s 410 and 471 - - such as submi t t i ng t he bi l l s t o t he Senat e

    - - weeks or mont hs bef or e the t r i p t o Las Vegas, whi ch i s

    consi st ent wi t h a gr at ui t y t heor y. Hence, t he j ur y r easonabl y

    coul d have f ound t hat t he t r i p was a rewar d f or t hat pr i or conduct ,

    r at her t han t he qui d pr o quo f or Mar t nez' s l at er suppor t of t he

    bi l l s.

    Al t hough t he i nst r uct i ons al l owed t he j ur y t o convi ct

    Br avo and Mar t nez of vi ol at i ng 666 by gi vi ng or accept i ng

    gr at ui t i es, t her e r emai ns t he mor e di f f i cul t quest i on of whet her

    t hi s i nst r uct i on was l egal l y er r oneous. We have never deci ded

    whet her 666 cr i mi nal i zes gr at ui t i es i n addi t i on t o br i bes, as t he

    i ssue has never been squarel y bef ore us. We now t ur n t o t hat

    quest i on.

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    B. Section 666

    1. Statutory Context

    We or di nar i l y begi n wi t h t he pl ai n l anguage of a st at ut e

    i n assessi ng i t s meani ng. See Uni t ed St ates v. Lachman, 387 F. 3d

    42, 50 ( 1st Ci r . 2004) . Her e, however , much of t he r el evant

    l anguage or i gi nat es i n anot her pr ovi si on, 18 U. S. C. 201, and i t

    i s t her ef or e usef ul t o t ake a st ep back and pl ace 666 i nt o

    st at ut or y cont ext bef or e l ooki ng at i t s speci f i c l anguage.

    Sect i on 666 "was born as t he st epchi l d of another

    st at ut e, 18 U. S. C. 201. " J ust i n Wei t z, Not e, The Devi l i s i n t he

    Det ai l s: 18 U. S. C. 666 af t er Ski l l i ng v. Uni t ed St at es, 14 N. Y. U.

    J . Legi s. & Pub. Pol ' y 805, 816 ( 2011) . Sect i on 201 cr i mi nal i zes

    br i bes and gr at ui t i es on t he par t of f eder al of f i ci al s. The

    st at ut e separ at es t he cr i mes of i l l egal br i bes and i l l egal

    gr at ui t i es i nt o t wo sect i ons: 201( b) out l aws t he of f er i ng of

    br i bes t o publ i c of f i ci al s, as wel l as t he accept ance of br i bes by

    t hose of f i ci al s, whi l e 201( c) out l aws t he of f er i ng and accept ance

    of i l l egal gr at ui t i es. 18 U. S. C. 201( b) , ( c) .

    The scope of 201 i s l i mi t ed t o t hose "act i ng f or or on

    behal f of t he Uni t ed St at es. " As the Senat e Repor t f or 666

    not ed:

    Wi t h r espect t o br i ber y, 18 U. S. C. 201gener al l y puni shes cor r upt payment s t o f eder alpubl i c of f i ci al s, but t her e i s some doubt ast o whether or under what ci r cumst ances per sonsnot empl oyed by t he f eder al gover nment may beconsi der ed as a "publ i c of f i ci al " under t he

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    def i ni t i on i n 18 U. S. C. 201( a) as anyone"act i ng f or or on behal f of t he Uni t ed St at es,or any depar t ment , agency or branch ofgover nment t her eof , i ncl udi ng t he Di st r i ct ofCol umbi a, i n any of f i ci al f unct i on. " Thecour t s of appeal s have di vi ded on t he quest i on

    whet her a per son empl oyed by a pr i vateor gani zat i on r ecei vi ng Feder al moni es pur suantt o a program i s a "publ i c of f i ci al " f orpur poses of sect i on 201.

    S. Rep. No. 98- 225, at 369 ( 1983) , r epr i nt ed i n 1984 U. S. C. C. A. N.

    3182, 3510. Spur r ed by t he Supr eme Cour t ' s pendi ng consi derat i on

    of t he meani ng of 201 i n Di xson v. Uni t ed St ates, 465 U. S. 482

    ( 1984) , whi ch sought t o r esol ve whet her 201 appl i ed t o st ate and

    l ocal of f i ci al s, Congr ess creat ed 666 as par t of t he

    Compr ehensi ve Cr i me Cont r ol Act of 1984 ( "CCCA") , Pub. L. No.

    98- 473, 98 St at . 1837 ( 1984) . Accordi ng t o t he Senate Repor t , t he

    pur pose of 666 was t o "augment t he abi l i t y of t he Uni t ed St ates

    t o vi ndi cat e si gni f i cant acts of t hef t , f r aud, and br i ber y

    i nvol vi ng Feder al moni es whi ch ar e di sbur sed t o pr i vat e

    organi zat i ons or St ate and l ocal gover nment s pur suant t o a Feder al

    progr am. " 11 S. Rep. No. 98- 225 at 369; 1984 U. S. C. C. A. N. at 3510.

    Si gni f i cant l y, t he Senat e Repor t st at ed t hat 666 was t o be

    i nt er pr et ed "consi st ent wi t h t he pur pose of t hi s sect i on t o pr ot ect

    t he i nt egr i t y of t he vast sums of money di st r i but ed t hr ough Feder al

    11 Sect i on 666 has a separ at e pr ovi si on t hat cover s t hef t andf r aud. See 18 U. S. C. 666( a) ( 1) ( A) . That pr ovi si on i s noti mpl i cat ed i n t hi s case.

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    pr ogr ams f r om t hef t , f r aud, and undue i nf l uence by br i ber y. " S.

    Rep. No. 98- 225 at 370; 1984 U. S. C. C. A. N. at 3511 ( emphasi s added) .

    As or i gi nal l y enact ed as par t of t he CCCA, t he 1984

    ver si on of 666 di f f er ed somewhat f r om t he cur r ent l aw. For

    i nst ance, what i s now 666( a) ( 2) was or i gi nal l y 666( c) , whi ch

    r ead i n r el evant par t :

    ( c) Whoever of f er s, gi ves or agr ees t o gi ve anagent of an or gani zat i on or of a St at e orl ocal gover nment agency . . . anythi ng ofval ue f or or because of t he r eci pi ent ' sconduct i n any t r ansact i on or mat t er or anyser i es of t r ansact i ons or mat t er s i nvol vi ng$5, 000 or mor e concer ni ng t he af f ai r s of suchor gani zat i on or St ate or l ocal gover nmentagency, shal l be i mpr i soned not more t han t enyear s or f i ned not mor e than $100, 000 . . . .

    18 U. S. C. 666( c) ( 1984) ( emphasi s added) . Sect i on 666 was

    amended i n 1986 as par t of t he Cr i mi nal Law and Pr ocedure Techni cal

    Amendment s Act of 1986 ( "CLPTA") , Pub. L. No. 99- 646, 100 St at .

    3592 ( 1986) . The House Repor t not ed t hat " t he enact ment of t he

    CCCA came dur i ng t he f i nal weeks of t he 98t h Congr ess, and, due t o

    demandi ng t i me const r ai nt s, t he CCCA cont ai ned a number of

    ambi gui t i es and t echni cal def ect s. " H. R. Rep. No. 99- 797, at 16

    ( 1986) , r epr i nt ed i n 1986 U. S. C. C. A. N. 6138. The pur pose of t he

    CLPTA was " t o el i mi nat e these techni cal def ect s and t o make mi nor

    subst ant i ve r evi si ons. " I d. Wi t h r espect t o 666 speci f i cal l y,t he House Repor t cl ar i f i ed t hat sect i on 42 of t he CLPTA amended the

    st at ut e " t o avoi d i t s possi bl e appl i cat i on t o accept abl e commer ci al

    and busi ness pr act i ces. " I d. at 30. The Repor t expl ai ned f ur t her :

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    anyt hi ng of val ue t o a publ i c of f i ci al "wi t h i nt ent . . . t o

    i nf l uence" an of f i ci al act, i d. 201( b) ( 1) ( A) , and on a publ i c

    of f i ci al who agr ees t o accept a t hi ng of val ue "i n r et ur n f or

    . . . bei ng i nf l uenced i n t he per f or mance of any of f i ci al act , " i d.

    201( b) ( 2) ( A) . As the Supr eme Cour t not ed i n Sun- Di amond,

    201( b) ' s i nt ent l anguage i mpl i es t hat " f or br i ber y t her e must be

    a qui d pr o quo - - a speci f i c i nt ent t o gi ve or r ecei ve somet hi ng of

    val ue i n exchange f or an of f i ci al act . " 526 U. S. at 404- 05.

    The second r el evant al t er at i on i s t he addi t i on of t he

    wor d "cor r upt l y" t o t he begi nni ng of 666( a) ( 1) ( B) and ( a) ( 2) .

    Congr ess nei t her expl ai ned t he r eason f or t hi s change nor def i ned

    t he t er m. However , t hi s i s another i nst ance wher e t he l anguage of

    666 was amended i n a way that br ought t he st at ut e cl oser t o

    201' s br i ber y pr ovi si on. Sect i on 201( b) ( 1) puni shes one who

    "cor r upt l y gi ves, of f er s or pr omi ses anyt hi ng of val ue t o any

    publ i c of f i ci al , " i d. 201( b) ( 1) ( emphasi s added) , and puni shes a

    publ i c of f i ci al who "cor r upt l y demands, seeks, r ecei ves, accept s,

    or agr ees t o r ecei ve or accept anyt hi ng of val ue, " i d. 201( b) ( 2)

    ( emphasi s added) . The word "cor r upt l y" does not appear i n

    201( c), t he gr at ui t i es pr ovi si on.

    Wi t h thi s backgr ound i n mi nd, we now anal yze t he t ext and

    st r uctur e of t he st at ut e.

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    2. The Meaning of 666

    The t ext of 666 has r emai ned l ar gel y unchanged si nce

    t he 1986 amendment s. Today, t he st at ut e r eads i n r el evant par t :

    ( a) Whoever . . . - -

    ( 1) bei ng an agent of an or gani zat i on, or of aSt at e, l ocal , or I ndi an t r i bal gover nment , or anyagency t her eof - -

    . . . .

    ( B) cor r upt l y sol i ci t s or demands f or t hebenef i t of any per son, or accept s or agr eest o accept , anythi ng of val ue f r omany per son,i nt endi ng t o be i nf l uenced or r ewar ded i nconnect i on wi t h any busi ness, t r ansact i on, orser i es of t r ansact i ons of such or gani zat i on,gover nment , or agency i nvol vi ng anyt hi ng ofval ue of $5, 000 or more; or

    ( 2) cor r upt l y gi ves, of f er s, or agr ees t o gi veanyt hi ng of val ue t o any per son, wi t h i nt ent t oi nf l uence or r ewar d an agent of an or gani zat i on orof a St at e, l ocal or I ndi an t r i bal gover nment , orany agency ther eof , i n connect i on wi t h anybusi ness, t r ansact i on, or ser i es of t r ansact i ons

    of such organi zat i on, government , or agencyi nvol vi ng anythi ng of val ue of $5, 000 or mor e;

    shal l be f i ned under t hi s t i t l e, i mpr i soned not mor e t han10 year s, or bot h.

    18 U. S. C. 666( a) . One of t he most conspi cuous di f f er ences

    between t he t ext s of 666 and 201 concerns t he i nt ent el ement :

    whi l e 666 pr ohi bi t s one f r om cor r upt l y of f er i ng a t hi ng of val ue

    wi t h i nt ent t o " i nf l uence or r ewar d" an agent , and pr ohi bi t s anagent f r om cor r upt l y sol i ci t i ng or demandi ng a t hi ng of val ue wi t h

    i nt ent t o be "i nf l uenced or r ewar ded, " t he br i ber y pr ovi si on

    appl i cabl e t o f eder al of f i ci al s, 201( b) , does not i ncl ude t he

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    al t er nat i ve "r ewar d": i t pr ohi bi t s one f r om cor r upt l y of f er i ng a

    t hi ng of val ue wi t h i nt ent t o "i nf l uence" an act , and pr ohi bi t s an

    of f i ci al f r omcor r upt l y sol i ci t i ng a t hi ng of val ue wi t h an i nt ent

    t o be " i nf l uenced. " The wor d " r ewar d" i n 666 i s open t o ( at

    l east ) t wo di f f er ent i nt er pr et at i ons. 12

    Under t he f i r st i nt er pr et at i on, when a payor i nt ends t o

    i nf l uence an of f i ci al ' s f ut ur e act i ons, t he payment const i t ut es a

    br i be; when a payor i nt ends t o r ewar d t he of f i ci al ' s past conduct

    ( or f ut ur e conduct t he of f i ci al i s al r eady commi t t ed t o t aki ng) ,

    t he payment const i t ut es a gr at ui t y. Uni t ed St at es v. Ander son, 517

    F. 3d 953, 961 ( 7t h Ci r . 2008) . Sever al ci r cui t s have adopt ed t hi s

    r eadi ng of t he l anguage. I d. ; Uni t ed St at es v. Gani m, 510 F. 3d

    134, 150 ( 2d Ci r . 2007) ( " [ A] payment made t o ' i nf l uence' connotes

    br i bery, wher eas a payment made t o ' r eward' connotes an i l l egal

    gr at ui t y. " ) ; Uni t ed St at es v. Zi mmer man, 509 F. 3d 920, 927 ( 8t h

    Ci r . 2007) ( ci t i ng 666( a) ( 1) ( B) ' s "i nf l uenced or r ewar ded"

    l anguage i n suppor t of f i ndi ng t hat "Sect i on 666( a) ( 1) ( B) pr ohi bi t s

    bot h t he accept ance of br i bes and t he accept ance of gr at ui t i es

    i nt ended t o be a bonus f or t aki ng of f i ci al act i on") ; Uni t ed St at es

    v. Agost i no, 132 F. 3d 1183, 1195 ( 7t h Ci r . 1997) .

    Under t he second i nt er pr et at i on, t he word " r eward" does

    not cr eat e a separ at e gr at ui t y of f ense i n 666, but r at her ser ves

    12 Unf or t unat el y, t he l egi sl at i ve hi st or y cont ai ns no cl uesabout why t hi s wor d was added i n t he 1986 amendment s.

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    ' cor r upt l y' shoul d be i nt er pr et ed t o cover gr at ui t i es, when under

    201 any payment made ' cor r upt l y' i s a br i be, not an i l l egal

    gr at ui t y. " I d. ( emphasi s added) . I f t he i ncl usi on of t he wor d

    "r eward" i n 666 does no more t han cl ar i f y t hat t he payment of a

    br i be can occur af t er t he act t hat i s t he subj ect of t he br i be i s

    compl et ed ( so l ong as t he agr eement t o pay t he br i be f or t he act or

    act s i s made bef or e t he act or act s t akes pl ace) , t he st at ut e st i l l

    appl i es onl y t o br i ber y, and t he use of t he wor d "cor r upt l y" i n

    666 woul d compor t wi t h the use of t he same wor d i n 201( b) : any

    payment made "cor r upt l y" i s a br i be. 13 Cf . Ander son, 517 F. 3d at

    13 The Second Ci r cui t t ook a di f f er ent vi ew of "cor r upt l y, " i nkeepi ng wi t h i t s pr i or concl usi on t hat 666 cover s gr at ui t i es. I nUni t ed St at es v. Bahel , t he Second Ci r cui t r ej ect ed t he def endant ' sar gument t hat t he j ur y char ge shoul d have speci f i ed t hat t hegovernment needed t o pr ove t hat he "' had been "cor r upt ed" at t het i me he act ed i n hi s of f i ci al busi ness. ' " 662 F. 3d 610, 638 ( 2dCi r . 2011) ( emphasi s added) . I nst ead, t he cour t concl uded t hat " i n

    t he case of a gr at ui t y, t he cor r upt i nt ent r equi r ed under Sect i on666 r ef er s t o an i ndi vi dual ' s st ate of mi nd at t he t i me the paymenti s r ecei ved. " I d. ( emphasi s added) . Thi s i nt er pr et at i on of"cor r upt l y" i s at odds wi t h t hat of t he Four t h Ci r cui t i n J enni ngs,whi ch woul d appear t o requi r e t he cor r upt i nt ent at t he t i me t heagent engages i n t he act t hat i s t he subj ect of t he r ewar d. Whi l eBahel ' s def i ni t i on of "cor r upt l y" suppor t s t he Second Ci r cui t ' si nt er pr et at i on of 666 as cri mi nal i zi ng gr at ui t i es as wel l asbr i bes, t he quest i on r ai sed i n J enni ngs r emai ns: i f "cor r upt l y" i nf act means not hi ng more than a l ack of an i nnocent mot i ve at t het i me one r ecei ves payment , why does 201 - - t he st at ut e upon whi ch 666 i s based - - f ai l t o i ncl ude t hat l anguage i n i t s gr at ui t y

    pr ovi si on when i t i s i ncl uded i n 201' s br i ber y pr ovi si on? I nother words, al t hough t he Second Ci r cui t pr ovi des an avenue bywhi ch the word "cor r upt l y" coul d be gi ven i ndependent meani ngwi t hout cabi ni ng 666 t o br i ber y, t hat i nt er pr et at i on woul d seemt o vi t i at e t he i ndependent meani ng of t he same word i n 201 - -agai n, an i mpor t ant consi der at i on gi ven t hat 666 was based on 201.

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    961 ( "Unl i ke a gr at ui t y, a br i be i s a payment made wi t h ' a cor r upt

    pur pose, such as i nduci ng a publ i c of f i ci al t o par t i ci pat e i n a

    f r aud or t o i nf l uence hi s of f i ci al acti on. ' " ( quot i ng U. S. S. G.

    2C1. 1 cmt . backgr ound) ) .

    Anot her cr i t i cal di f f er ence bet ween 666 and 201 i s

    t he maxi mum penal t y aut hor i zed under t he st at ut es. One who

    vi ol at es 201( b) , t he br i ber y pr ovi si on, may be f i ned, "or

    i mpr i soned f or not mor e t han f i f t een year s, or bot h. " 18 U. S. C.

    201( b) ( emphasi s added) . For a vi ol at i on - - any vi ol at i on - - of

    666, t he st at ut e pr ovi des a puni shment of a f i ne, a t er m of

    i mpr i sonment of "not more t han 10 years, " or bot h. I d. 666( a)

    ( emphasi s added) . An even more st r i ki ng di f f er ence i n penal t i es,

    however , exi st s bet ween 666 and 201' s gr at ui t y subsect i on, t he

    l at t er of whi ch cal l s f or a t er m of i mpr i sonment of "not mor e t han

    t wo years, " i d. 201( c) ( emphasi s added) - - meani ng t hat 666

    aut hor i zes a t er m of i mpr i sonment f i ve t i mes l onger t han t hat

    al l owed by 201' s gr at ui t i es pr ovi si on.

    Thi s dr amat i c di scr epancy i n maxi mum penal t i es between

    666 and 201( c) makes i t di f f i cul t t o accept t hat t he st at ut es

    t ar get t he same t ype of cri me - - i l l egal gr at ui t i es. The

    di f f er ence i n sent ences cont empl ated by 201( b) and 666 i s bot h

    l ess dramat i c and mor e under st andabl e: 201( b) t ar get s ( pr i mar i l y)

    f eder al of f i ci al s, whi l e 666 t ar get s non- f eder al of f i ci al s who

    happen t o have a connect i on t o f eder al f unds. I t i s r easonabl e t o

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    assume t hat t he f eder al gover nment vi ewed cor r upt f eder al of f i ci al s

    i nvol ved i n t he r ecei pt of br i bes as mor e cul pabl e. 14

    The di st i nct penal t i es f or br i bes and gr at ui t i es

    cont ai ned i n 201 hi ghl i ght s an obvi ous yet i mpor t ant st r uct ur al

    di f f er ence bet ween 666 and 201: 666 does not have separ at e

    br i ber y and gr at ui t y subsect i ons. For t hose ci r cui t s t hat have

    f ound t hat 666 cr i mi nal i zes gr at ui t i es, t wo subsect i ons of 666

    do t he same work as f our subsect i ons of 201. We t hi nk i t

    unl i kel y t hat Congr ess woul d condense t wo di st i nct of f enses i nt o

    t he same subsect i on i n 666 when t he st at ut e upon whi ch i t i s

    based has separat e subsect i ons f or each of f ense. See Geor ge D.

    Br own, St eal t h St at ut e - - Cor r upt i on, t he Spendi ng Power , and t he

    Ri se of 18 U. S. C. 666, 73 Not r e Dame L. Rev. 247, 310 (1998)

    ( "Congr ess di d not . . . enact a mi r r or i mage of 201 f or

    nonf eder al of f i ci al s. Sect i on 201 cont ai ns separ at e subsect i ons to

    deal wi t h br i ber y and gr at ui t i es. Sect i on 666 does not . I t i s a

    mi st ake t o at t empt t o r ead t he t wo st at ut es as equal i n r each. " ) .

    Fur t her more, i f Congr ess di d choose t o condense br i bes and

    gr at ui t i es i nt o a si ngl e pr ovi si on i n 666, i t woul d be odd t o do

    so by mer el y pl uggi ng sl i ght l y modi f i ed l anguage f r om 201( b) , i t s

    br i ber y pr ovi si on, i nt o t he st at ut e. Sur el y t he wor d "gr at ui t y" - -

    14 The l egi sl at i ve hi st or y of 666 sheds no l i ght on t her eason f or t hese di f f er ences i n penal t i es.

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    whi ch i s, of cour se, ment i oned nowher e i n t he t ext or l egi sl at i ve

    hi st or y of 666 - - was not f or ei gn t o Congr ess i n 1986.

    Al t hough 666 was enact ed t o suppl ement 201, we can

    easi l y hypot hesi ze at l east t wo r easons why Congr ess may have

    chosen t o suppl ement onl y 201' s pr ohi bi t i on of br i ber y. Fi r st ,

    br i bes ar e si mpl