The H on orable M atthew F. K ennell y, Un it ed Stat es D is tr ic t  Cour tf or the N or the rnD i s t ri c tofI l l i noi s , s i t t i ng by des i gna t i on.



## In the 

# U n ited S ta tes Co urt o f Ap p ea ls

F o rth eS e v e n th C ir cu it
N o. 09

- 1443 U NI T ED S T A T E SOF A MERI CA, P la intif f-A pp ellee, v. K ERRY L. S MITH, D ef endant-Appellant.

A pp eal from the United S t ates Di strictC our t fo r the S outhernDi stricto f Illino is. No . 4:07- cr-40038- GPM- 1

— G . Patri ckMu rp hy, Judge .
A RGUED J AN UA RY 19, 2010

— D ECIDED A UGUS T 19, 2010

Befo re B AU ER a nd W OO D , C i r c u it Judges, an d K ENNELL Y, D i s t r i ctJudg e .  K E NN E LLY, D is t r i ctJudg e . Kerr y S m i th pl ed gui l ty to cr i m i na lc ha r g es pur su an t to a wri tt enpl ea a g r ee m en t a n d w a s s e nt e nc e d t o a n i n e t y - t wo mo n th p r i s o n t e r m. H e ap p ea ls, c on te n d in g th at th e d ist ric t c ou rterr on eo u sly2 N o. 09

- 1443 d ep riv ed h im of h is Six th A m en d m en t rig h t t o re ta in t h e c o u n s e lo fh i s c h o i c e . F o r th e r e a s o n s s t a t e d b e l o w, w e v acat e S m i th’s c onvict i on a nd r em and w i th i nstr ucti ons to perm i t hi m to withdraw his gui l ty ple a.

I. F AC TS I n Apr i l2 00 7, a g r an d j ur y i ndi ct ed Ker r y S m ith o n a charg e o fco nspir acy to dist ribute m ar ij u ana. S m i th r eta i ne d a tt o r ne y J o hn Ro g er s to r epr es en t hi m . The di st r i ctcou rt o r i g i na l l y s etthe c as e f o r t r i ali n mi d-J une 2007but l ate r continued the tr i alto S eptem ber20 07. I n J ul y 2 00 7, th e g r an d j ur y r etur ne d a s upe r se di ng i nd ict m ent. The super sedi ng i nd i ctm ent a dd ed char ges ofm oneyl aund er i ng, co ncealm ent o fi nfo rm ati on fro m th e S oci alS ecuri ty A dm i ni str ati on, and m aking f al se sta tem ents. The tr i alwas continued , but the r eco rd does not re fl ect that a new date was se t. Disc ove ryi n the case w as vol um i nous. In M ar ch 200 8, Sm ith ’ s c o u n se l R og er s filed a m ot ion to su p p re ss ev iden ce a nd a mot i o n t o s ev erc ha r g es . The c as e was put on hol d, how eve r, afterRoge rs r equeste d and th e j ud ge or dered a com petency evaluati on o fS m i th. The ev al uati on was co m ple ted i n J une 200 8. The docke t d oes not r efl ec t th at a ne w tr i alda te was s etb efo r e o r a fte r the co m pl et i o n o fthe e va l ua ti o n. On A u gu st 25, 20 08, S m i th fi l ed a m oti on a sking to su bs ti tu te a ne w re ta i ne d a tt o r ne y, Be au Br i ndl ey . The m oti on ci ted S m i th’ s co nsti tuti onalr i ght t o the c ounselN o. 09

- 1443 3 of his ch oice. Th e record doe s not reflect t h at th e cou rt had set a t ri aldate at that poi nt. Sm i th’ s m oti on t o substi tute counselwas cal l ed f or he aring on Sep tem ber 8, 2 0 0 8. Prior to the he aring, th ere w as sti l lno i nd i cati on that the di str ict c ou rt had seta tr i alda te
. At the he ar i ng, the di st r i ctc o ur t fi r st f o und Sm ith co m p et en t t o s ta n d tria l. The cour t then tur n ed to S m i th’ s m oti on t o substi tute B rin d ley as h is d efe n se co u n se l. T h e c ou rtinit ially sta ted thatit w as i ncl i ned to perm i t s ubsti tuti on o f cou ns el. I t stated , how ever, t ha t “th e case is goi ng to j ury tr i alN ov em b er 4 th. I ’ m go i ng to pi ck a j ury the F ri day bef o r e a nd i f you are not read y you ca n’t su bstitu te. So i t ’ s j u s t th a t s i mpl e . ” S e p t
. 8 , 2 0 0 8 T r . 4
. T h i s wa s th e fi rs t t i m e the co urt had m ade r efer en c e to a t ri aldate, an d as we h a v e n o t e d th e r e c o r d c o n t a i n s n o e a r l i e r me nt i o n th a tth e c o ur t h a d s e tth e c a s e f o r t r i a li n N o v e mbe r ( o r, f o r tha t m at te r, a ny o th er d ate)
. At o r ala r g um ent b ef or e us, the gov er nm ent c onceded thatno tr i al dat e ha d been se t pr i o r t o the S ept embe r 8 , 2 00 8 he ar i ng an d that there h ad been no ind ication th at th e cou rt i ntended to tr y the ca se i n N ove m ber20 08. A fter further disc ussi on, the dist ri ct court inqu i re d when Br i ndl ey ha d fi l ed th e pr o po se d m o ti o n s ubs ti tu
ti on o fco unsel

. Bri nd l ey sai d h e h ad fi l ed the m oti on seve ra lweeks ear l i er, and the cour t cl er k r epor ted that the m oti on had bee n fi l ed on Au gust 25. The di str i ct c o u r tth e n s t a t e d , “ T h i s m a t t e r h a s b e e n s e tf o r s o me t i me. Lind a , a nn o un c e the t r i a lda t e . ” T he c l e r ks t a t e d, “J ury sel ecti on N ove m ber 3r d; tr i al w i l lbe N ove m ber4th4 N o. 09

- 1443

W e not e thatthe dat e the c l er k a nno unc ed for j ur y s el ec t i on 1 w as a M o n d a y , not “the Fri day bef ore” the purp orte d tri al da t e a s the di s t r i c tc ou r th a d e a r l i e r s t a t e d. at 8:00 a.m .” Id. at6
. Br i ndl eyt o ld th e cou r t th athe 1 was s c h e d u l e d t o b e o n t r i a li n a mu l t i p l e - d e fe n d an t ra cket eer i ng co nspir acy case from O cto ber6 thro ugh the beginning of Decem ber

. The cour t then sai d, “Y ou don’thave any busi ne ss in thi s ca se. You don’ t hav e ti m e t o do i t. ” Id. at7. Th e f o l l o wi ngc o l l o qu y e ns ue d: M R. BR I NDLEY : M r. Sm ith h as a c on st itu ti onal

rig h t t o c h oic e o f co u n se l. THE COURT: N o , h e d o es n o t. He had a co ns t i t uti ona l r ight t o coun sel
. He doesn’ t havea con s t i t ut i onal r ightt o pi ckan y perso n h e w a nted
. I f thatwas the case , we w ou l d have Bre nd an Su lliva n or E d w ar d B e n n et t W ill i am s o r an y num bero fat torneys. You don’tnece ssa ri l y g et that. M R. BRIND LE Y: H e get s

— un d er the C ons ti tu ti o n,

Ibel i eve , yo ur Honor, h e g ets w h oe ve r h e ca n affo rd an d is wi l l i n gt o r e p r e s e n th i m. THE COUR T: Bu t he doesn’ t g e th i s schedule

.

And tha t’ s what we’ r e ta l k i ng about he re . Now , I ’ m te l l i ng y ou th at o n N ov em b er 4t h on [sic ] th isN o. 09

- 1443 5 ye ar , th is c a s e i s g oin g t o t ria l. No w i fy o u tel lme y o u c a n’ tdo it, yo u ca n ’ t d o it. B u t t h is c as e is go in g t o t ria l N ov em b er 4t h . It is not a sub j ect f or discu ssion or a to pi c up f o r de ba te
. Iha ve no th i ng butm att er s se t be twe enno w and then. M y s chedule i s what i t i s. T h i s i s th e t i me I ’ v e g o t t o t r y t he case . I ’ m go i ng to l et the three o fyo u disc us s it a nd deci de w hat y ou ar e g oi ng to do. Bu t y our case wa s a l r e a dy s e t i n Ch i c a g o . You ar e g o i ngto ha ve t o wor ka r o und that, o r w here veri t i s. N ow, the Cour t’ s in re c ess f or fi ve m i nutes. Id. Tr. 7-8 (em p ha sis add ed ). A fterthe fi ve m i nute r eces s, S m i th’ s o ri ginalr eta i ned co uns el, Ro g er s, r epo r ted th atS m i thdi d no t want Roger s t o continue to re prese nt hi m . Roge rs i nd i cate d that Sm i th had bee n opposed to Roge rs ’ earlier r equest f o r a c o m petency e xa m i na ti o n a nd tha t th ei r r el at i o nshi p had d ete ri or ate d as a r esul t. The co urt perm i tte d Roger s t o w i thdraw and st ruck hi s a pp ear ance. The cour t, ad d ressing S m i th, r epeate d that the cas e w as set for tria l on N ovem ber 4

— l es s th ant wo months h en c e. The cour t t ol d Sm i th that“[ i ] fyo ur l aw yercan6 N o. 09

- 1443 b e h er e a n d rep re se n t y ou th at is fin e w ith t h e C o u r t. If he can’ t, Iwil lappoi nt a l aw yerf oryo u w ho wil lbe re ady o n N ovem b er4th. S o i t’ s r eal l y up to M r. Bri nd l ey w hethero r not he i s g oi ng to rep re se nt yo u i n the m atter
. ” Id. at9. Bri nd l ey re peated that he had l ong b ee n set for tr i a l in t h e o th er ca se an d w as th er efo re u n av aila b le on N ove m ber4. The cour t deni ed Sm i th’ s m oti on t o substi tute counsel an d st at ed, “[ t] he Cou r t wi l l appo i nt co uns el for th e defe nd ant a nd yo u w ill hear fro m us s hor tl y. ” Id. at10
. Sm i th the n ask ed t h at hi s o ri gi nalat torney, Roge rs , con tinu e to repre s e n t h im , bu t the cou rt de nied Sm ith’s re quest. The co urt al so denie d Sm i th ’s re quest ( thro ugh Br i ndl ey ) f o r a c o nt i nua nc e. W e quo te the c o l l o quy fro m the hear i ng: THE COU RT: M r. Sm ith

. . . [ d] o y o u ha ve the m eans and app ar ently enough m ea ns t o hi r e pr i va te c o unsel. S o i fyo u

— Iwi l lg o a head and app oi nt yo u a l aw yerf or N ove m ber 4th and i f yo u can g ets o m eo ne dow n her e o fy o ur own choo si ng be f or e then, that w i l lbe fi ne. MR
. S MI T H: I f Mr
. B r i n d l e y c a n’ t de f e n d me Istil l w an t to go w ith Roge rs th en . T H E C O U R T : S o met i mes that

— so m et i m es that’ s ki nd o fl i ke dati ng. Once yo u get

— o n c e yo u g e tth r o wnN o. 09

- 1443 7

o utthe f r o ntdo o r y o u mi g ht n otw an t t o c om e in

— M R. SM I TH : Ij ust e xplaine d t o b ot h o f them a se co nd a g o . Imean, i fhe coul dn ’ t t ake o verthe case I

— THE COUR T: W el l , I’ l l take a no the r b ri ef re cess . I ’ l lbe out in fi ve m i nutes. Idon ’t know h o w M r. Roge rs feel s about that. H e d oesn ’t w an t to do it. H e’s o u t. T ha t’s w ha t Ithou gh t. So th at be in g t h e c as e, w e’ll

— M R. BR I NDLEY : You r H on or , j ust f or the re co r d, f o r p ur po s e s o fth e r e c o r d, M r . S m i thwoul d r eque sta conti nuance so thatIbe al l owed to t a k e th e c a s e s i n c e I a m t he counselo fhi s pre fer ence. THE COUR T: There’ s t wo t hi ngs a bout that. You’r e no t in thi s ca se. M R. BR I NDLEY : Th a tIu nd e r s t a nd

. THE COUR T: So I ’ l l t al k t o hi m abo ut that. Your m oti on t o subst itu te i s deni e d. M R. B RI N DL EY : W oul d you i nquir e ofM r. S m i th th en . THE COUR T: Yo u a r e e xc us e d.8 N o. 09

- 1443 M R
. BR I N D L E Y : T ha nk you, your H onor. TH E C OU RT: You ar e wel com e. N ow, M r. S m i th. Ias sum e that

— the Cou rtdoes n’to rdi nari l y g et i nvol ved in the fi nanci alsi tuati ons, but I w oul d thi nk y ou have a r efund c o m i ng . I fy o u wan t to re tain i nd ependent counsel y o u c ando tha t. I n the mean ti m e, I ’ m go i ng to ge t a pp oi nted counselo n yo ur ca se an d I urge y o u to co o per at e wi th th i s p erson. N ove m ber4th w hat y ou n ee d to kn ow an d if yo u w ou ld check w i th peopl e that hav e b ee n in m y c ou rt, th is c as e is g o i ng to t r i al

. S o j us t do the best you can, I guess . You have m ade

— Ithinky o u ha v e ma de so m e dec i si o ns tha t y o u mi g ht fin d qu es t i on ab le, bu t y ou w ill geta f ai r tr i al

. A nd i f you can g ets o m eo ne he r e qui ck ly, the Court w ou l d ser i ousl y c onsi der l et tingthe m s ubs ti tu te in. Id. at10

- 12. La t e r tha t s a me da t e , the c o ur t e nt e r e d a n or der a ppo i n t i n ga n e w a t t o r n e y, R o n a l d J e n k i n s , t o r e p r e s en t S mi th

. J e n k i n s fi r s ta p p e a r e d b e f o r e t he co ur to n S e p t e mber 1 2 , 2 0 0 8
. He s t a t e d tha th e h a d fi r s ts po k e n t o S m i thN o. 09

- 1443 9 j us t be f o r e th e he ar i ng . J en kins al so i ndi ca te d tha t he w oul d be r ea dy to pr o ce ed o n th e tr i al dat e the cou rt had set. On Septem ber29 , 20 08, S m i th ent er ed a gui l ty ple a t o allo fthe charg es i n the superse ding i nd i ctm ent. T h is w as exactly three weeks a fterthe cour t had deni ed S mi th ’ s r e q u e s tt o a l l o w B r i n d l e y to r e p r e s e n th i m, and about tw o and one- hal fweeks afterJ enki ns fi rs t ap p ea re d

. Sm i th pl ed gu ilty pursuant to a wri tte n ple a a gr eem ent. The pl ea agr eem ent di d not incl ud e a ny wri tte n affi r m at i o n tha t S m i thwas a ct i ngv o l unt ar i l y whenhe si gned the agr eem ent. I t did , ho w eve r, i ncl ud e a st ate
m ent that S m i th “i s fully s ati sfi ed w i th the r epres entati on he has r ecei ved fro m hi s co unsel

. ” Pl ea A gr. ¶ I I I
. 1. The ple a a gr eem ent a l so i ncl ud ed the f ol l owing ter m s: 1. The De fen dan t unde r st an ds th atb y pl ead in g g ui l ty, he i s wai vinga l la ppel l at e i ss ue s tha t m i g ht ha ve b ee n a va i l ab l e i fhe ha d ex erci se d hi s r i g ht to tria l.

. . . 2. The De fen dan t i s awar e th at Ti tl e 18 , Ti tl e 28 , a nd oth er prov isi ons of th e U nited States C od e aff ord eve rydefendant l im i ted r i ghts to conte st a co nvi ctio n an d /or se n te n c e. A c kn ow le d g in g a ll th is, an d in ex ch an g e f o r the r ec o m m en dat i o ns a nd c o nc es si o ns m ade b y the Go ve r nm en t i n thi s pl ea a g r ee m en t, the D efe n d an t k n ow i n g l y a n d vo lu n ta rily w aiv es h is r i g htt o c o nt es t an y a spe cto fhi s co nv i cti on and se ntence thatco uld be co ntest ed und erTitle 18 o r T i t l e 2 8 , o r u n d e r a n y o th e r pr o vi s i o n o ffe d e r a ll a w,10 N o. 09

- 1443 except that i fthe sente nce i m posed i s in ex cess o f th e S en te nc i ng Gui del i ne s as det er m i ne d by the Cou r t (ora ny a ppl i cabl e st atut o r y min i m um , whi ch

eve r i s g re ate r) , the Defe nd ant r ese rv es the r i gh t to ap p ea l th e re as on ab len es s o f th e s en te n c e. . . . 3. Defen dan t’ s wai ve r o fhi s ri g htt o a ppea lo r b r i ng col l ate ra lchal l enges shal lnot a pp l y t o: 1) any subseque ntc ha ng e i n the i nt er pr et at i o n o fthe l aw b y the U ni ted S tat es Suprem e Cour t o r the Unite d States C ou rtofA p p ea ls for th e Se ve n th C irc u it, w h ich is decl ar ed retr oac ti ve by thos e Cour ts, and w hi ch r en der s th e Defen dan t ac tu al l y i nno ce nto fthe charg es cove re d here i n, and 2) appeals base d up on S e nt e nc i ngGu i de l i ne a men dment s wh i c h a r e ma de r e t r o a c t i v e b y th e U n i t e d S t a t e s S e n t e n c i n gC o mm iss ion (se e U .S.S.G . § 1B 1.1 0). . .
. Pl ea A gr . ¶¶ I I I
. 1- 3. Dur i ngthe g ui l typl ea c o ll oquy, a tt o r ne y J en k i ns sta ted thathe ha d revi ew ed the fi l e that he had re cei ved fro m S m i th’ s prior c ou nseland had m et w i th Sm i th “fora si gni fi cant peri od ofti m e o ne day” to re vi ew ev i den ce . S ept. 2 9, 2 00 8 Tr
. 5
. J en k i ns s ta te d tha t o n the F r i dayb efo r e th e g ui l typl ea he ar i ng, he had a pho ne c all w i th S m i th, wh o w as i n custo dy pend i ng trial. J en k i ns had metwi thS m i tha g ain the mor ni ngo fthe gui l ty ple a. Aft e r qu e s t i o n i n gS mi th, th e c o u r tf o u n d h i m c o mpe t e nt
. T he c o ur te l i c i t e d S mi th’ s a g r e e men ttha th e h a d, i n the c o ur t’ s wor d s, “p lenty o ft i m e” t o di sc us s th e ca se wi thJ en k i ns a nd tha t he was s at i sfi ed wi thJ en k i nsN o. 09

- 1443 11

as a law ye r. Id. at7- 8. The co urt asce rt ai ne d that S m i th unde r st o o d th e r i g ht s he woul d g i ve up bypl ea di ng gu ilty

. Id. a t 8- 10
. A fter di sc us singthe e l ement s o fthe offe n se s c h ar ge d an d th e p os sib le p en alt ies , i d. at10

- 14 & 15

- 17, the cour t a ske d Sm i th wh etheranyo ne had thr eat
ened orf or ced hi m to pl ead g u ilty, and Sm i th sa i d no. Id. a t 14
. Thi s was the onl yr efer en ce t o v o l unt ar i ne ss ; the cour t di d not a sk Sm i th wh etheran y p ro m i ses had bee n m ade to hi m and did notdi re ctl y a sk w hetherh e was ac tin g v olu n ta rily o r of h is fre e w ill. See F ed. R. Cr i m . P. 11(b)(2) (requ iring cou rt to “ad d ress th e d efen d a nt perso n ally in o p en co u rtan d d et er m in e t h at th e p le a is v o l u n t a r y a n d d i d n o tr e s u l t fr o m f o r c e , th r e a t s , o r p r o mises ( oth er than prom ises i n a p lea agreem en t)). ” Th ere w as als o a br ief, th ou gh ob liqu e, r e f e r e n c e t o th e a p p ellat e w aiv er , w h ich w e w ill d i s c u ss sh or tly

. Id. a t 17
. The cou rt eli cited from Sm ith a statem en t tha t the m a tters sta te d i n a s epara tel y- fi l ed sti pu l ati on o ff acts were tr ue. Id. a t 18
. Af te r s o m e fur th erdi sc us si o n, th e c o ur t f o und th at Sm ith ’s p lea w as kn ow in g a n d vo lu n ta ry . Id. at20
. I n Feb ruar y 2 009, the dist ri ct c ourti m posed a pri son sente nce o fni nety- tw o m onths. S m i th fi l ed a no ti ce o f a p p e a l

. T h e g o v e r n me n t mo v e d t o d i s mi s s th e a p p e a l

. We c o ns o l i da t e d the mo t i o n wi th a r g ume nto n the me r i ts and dir ecte d the par ti es to add re ss i n thei r m er i ts bri ef s whether Sm i th’ s guil ty ple a was vo l untary
.

III. D I SC US SI ON Sm ith co n te n d s t h at th e d ist ric t c ou rtvio lat ed h is Six t h A m en d m en t rig h t t o c ou n se l w h en it d en ied h is12 N o. 09

- 1443

m otion to su bstitu te B rin d ley as trial cou ns el. Be fore a d d ressing th e m erits, w e con side r the gove rnm en t’s c on te n tio n th at Sm ith w aiv ed h is rig h t t o a p p ea l.

A . A pp el l at e W ai ver The go ve rn m ent has notar gued, ei theri n i ts m oti on to dism i ss ori n i ts bri ef, thatsi m plybyplea d ing guil ty, Sm i th waiv ed any conte nti on that the di str i ct c ourtvi ol at ed hi s S i xth Am en dm en t r i g ht s. T he po i nti s thus l i k e l y f o r fe i t e d. F o r fei tu r e as i de, a ny s uchc o nt en ti o n wo ul d b e l ac k i ng inm er it. It is tr u e t h a t a n u n c on d itio n al g u ilty p lea ty p ical l y wai ves non-j uri sdic ti onaldefects in the pro

c ee d in gs be low

. Se eTol l e t tv. He nde rson , 41 1 U.S
. 25 8, 267 (1973 ). T he Sup rem e C ou rt has recen tly held, how ever, th at t he er ro neous depri vati on o fthe ri ght t o counsel o fc ho i c e i n v i o l a t i o n o fthe S i xth Am e nd men ti s a “ s t r uctura ler ro r” i n a c ri m inalpro ceedi ng and i s no t s ubj ect to harm l ess er ro r anal ysis. U n ited S ta tes v. G o nz a lez -Lo pez , 548 U
. S. 14 0, 15 0- 52 ( 2006 )
. The Courtst ate d that [ d]iffer ent a tto rney s wil lpursue differ ent s tr ate gi es. And the c hoice o fa tt o r ne y wi l la ffec t whethe r a nd o n wha t te r m s th e defend an t co o per at es wi ththe pros ecuti on, pl ea bar gains, o r d ecides i nstea d to go to tr i al

. In l i ght of these m yr i ad aspect s o fr epres entatio n, th e e rro n eo u s d en ial of c o u n se l be ar s d ire c tly on the fra m ew or k w i thi n w hi ch the tr i al p ro ceeds, o r ind eed on whethe ri t pr o ce eds a t al l

. . . . M an y counsel ed deci si ons, i ncl ud i ng tho se i nvol vi ng pl eaN o. 09

- 1443 13 bar gains and coo perat i on with the gov er nm ent, d o not ev en co n c er n th e c on d u c t o f th e t ria l atall. Id. at15 0. Re l y i ngo n G o nz a lez -Lo pez , th e F ifth C irc u it re c en tly he l d that a de fe nd a nt ’ s g ui l t y p l e a do e s n o tp r e c l ud e hi m fro m c hal l engi ng o n appeal a denia lo fhi s r i ght t o c ou n se l of c h oic e. U nited Sta tes v. Sa nc hez -G uerrero , 54 6 F. 3d 328, 33 2 ( 5th Ci r. 20 08 ). W e a gr ee. A s the Fi fth Cir cui t s tat ed, “i t i s obvi ous that the choi ce o fco unsel m ay ser i ousl y i m pact a defe nd ant’ s deci si on to pl ead gui l ty. ” Id. “ I fa d efend an t i s er r o ne o us l y de ni ed th e counselo fhi s cho i ce, i t i s a st ructur aler ror in t he tr i al th atb r i ng s i nt o que st i o n the v o l unta ry a nd i nt el l i g en t chara c te r of the gui l ty ple a i tse l f

. ” Id. Un d e r th e c i r c u msta nces, S m i th’ s guil ty ple a does notam ount t o a waiv er o fh i s S i x th A me n d me n tc h o i c e - o f

- c o u n s e lc l a i m. The go ver nm en t argues that Sm i th waiv ed the ri ght t o ap p ea l v i a the appel l ate waive r i n hi s pl ea agr eem ent. T h er e is n o q u es tio n th at a d efe n d an t m ay w aiv e h is rig h t t o a d ire c t ap p ea l as p ar t o f a p lea ag re em en t. See, e.g., Jo nes v. U nited Sta tes , 1 67F
. 3d 11 42 , 11 44 ( 7th Ci r . 1 99 9)
. But ap p ella te w aiv er s are n otblin d ly en for c ed

. See, e.g., U nited Sta tes v. R ho des , 3 30 F
. 3d 94 9, 9 52 ( 7th Ci r . 2 00 3)
. “ To deter m i ne i fa defe nd ant knew an d u nd er sto od the ple a agr eem ent, we m ust e xam i n e th e l anguage o fthe ple a agr ee m en t i ts el fa nd a l so l o o kt o the pl ea c o l l o quy between the defe nd ant and the j u d ge . ” U nited Sta tes v. Chapa , 60 2 F
. 3d 865, 86 8 ( 7th Ci r. 20 10) ( ci ti ng U n i ted Sta tes v. Sura , 511 F.3d 654 , 661 (7th C ir. 2007)).14 N o. 09

- 1443 The appell ate waive r i tse l fw as re aso nabl y c l ear . That, h ow eve r, i s not the end of the i nquir y. I f i t w as , Ru le 11 ( b) ’ s r equirem en t th atthe di st r i ctc o ur t addr es s th e d efe n d an t p er so n ally w ou ld be a d ea d let te r. Turningto the dist ri ct c ourt ’s col l oquy with Sm i th re ga rd in g t h e a p p ella te w aiv er , w e c on c lu d e t h at it fell shor t o fwh at the l aw r equi re s. Fe deralRule o fCri m i nal Pro cedure 11 w as am ended effecti ve Decem ber1, 19 99 “t o re flec t t h e in c re as in g p ra c tic e o f inc lu d in g p ro visi ons i n ple a a gr eem ents w hi ch r eq uir e the defendant to w aive cer tain appell ate r i ghts. ” F ed. R. Cri m . P. 11 , 19 99 advi sor y c om m i tt ee note s. The newly- add ed prov i si on st at es tha t th e di st r i ctc o ur t “musti nf o r m the de fen dan t of, an d d et er m in e t h at t h e d e fen d an t u n d er st an d s . . . th e te r m s o fa ny pl ea - agree m en t pr o vi si o n wai vingthe rig h t t o ap p ea l or to co llat er ally at ta c k t h e s en te n c e.” Fe d . R. C rim . P. 11 (b )(1) (N ). T h e d ist ric t c ou rterr ed by fail i n g d u rin g t h e p lea co ll oquy t o a dv i s e S mi th o fthe t e r ms o fthe a pp e l l a te w ai verand deter m i ne wh ethe r he underst oo d that pr ovis ion
. See Su ra , 5 11 F
. 3d at6 61

- 62
. S m i thdi d n ot ar g ue th i s o m issi o n b efo r e th e di st r i ctc o ur t, s o we r ev i ew the p oin t fo r p lain err or . U ni t e d S t at e s v. Vonn , 53 5 U.S
. 55 , 59 (20 02 ); Su ra , 51 1 F
. 3d a t 65 8. S peci fi cal l y, S m i th m ust show that hi s s ubstanti alr i ghts w er e a ffec te d and that the e rro r ser i ousl y a ffecte d the f ai rnes s, i ntegr i ty, o r p u b lic re p u ta tio n of th e c ou r t p ro c ee d in g. Vonn , 535 U
. S. at 62- 63. W e con clud e tha t Sm ith h a s m ad e the nec essary s ho wi ng . Fi r s t, S mi th’ s s ub s t a nt i a lr i g ht s we r e a ffe c t e d;N o. 09

- 1443 15 th e vi o l at i o n o f hi s S i xth Am en dm en t r i g ht s o cc ur r ed an d w as com p let e (a s we w i l ldi scuss) atthe ti m e the di str i ct c o ur tde ni e d his mo t i o n t o s ub s t i t ut e c o un s e l

. S e c o nd , th e er r o r ha d a s i g ni fi ca nte ffect on the f ai r ne ss o fthe proce edi ngs. The r i ght t o counseli s o ne o fthe bed rock el em ents prot ecting the f ai rnes s o fthe advers ar y pr oc es s. Se e, e . g., S trick l and v. Was hi ngt on , 46 6 U.S
. 66 8, 68 4 (1 98 4)
. The S upr eme Co ur t m ade i t cl ea r i n Go nzal e zLo pez th at “t h e rig h t t o s ele c t c ou n s e l of on e’s ch oic e . . . ha s been re g ar ded as the r o o t m ea ni ngo fthe c o ns ti tu
ti onalguar antee ” co ntai ned i n the Si xth A m end m en t. G o nz a lez -Lo pez , 54 8 U.S
. at14 7- 48. We th e r e f o r e c o n s i d e r w h e th e rth e t r i a lc o u r tc o mpl i ed wi thRul e 11 ( b) ( 1) ( N ) ’ s r eq uir ement s. Dur i ngthe cour se ofthe gui l ty ple a co l l oqu y, the c ourtdi d not expla i n, quote , o r ev en sum m ar i ze the a pp el l ate waive r to Sm ith . N or d i d i t e l i ci t fro m S m i th a sta tem ent that re aso nabl y c an be const rued as ind icati ng awarene ss that he was gi vi ng up hi s r i gh t to appeal fro m r ulings th e cou r t h a d prev iously m ad e. R ath er, the cou rt re fer re d to th e p lea ag re em en t’s ap p ella te w aiv er on ly oblique ly, and i n a brief que stion n ot to Sm ith him self, butt o the a tt o r ne y the c o ur t ha d a ppo i nt ed to r epr es en t h i m: TH E CO U RT: N o w n o t h av in g re ad all of th is

agr eem ent i s there a

— i s there an appeal waive r i n her e? M R
. J E N K I N S: Y es, sir. THE COU RT: A nd th e te r m s of th a t w a iv e r are

w hat?16 N o. 09

- 1443 MR
. J E NK I NS : Basi cal l y, yo ur Ho no r , t hat e ver ythi ng i s wai ved w i th the e xcepti on o f the r eas onabl eness o fthe sente nce. TH E C OU RT: A l lr i ght. M R. J EN K I N S: A nd he c an’ t withd ra w hi s pl ea. TH E C OU RT: You und er sta nd that ? M R
. SM I T H : Y es, you r H onor. Se pt. 29 , 20 08 Tr. 17
. This w as i nadequ ate , and i t di d n ot c om portwith the r equi re m ents ofRule 11 ( b) ( 1) ( N )
. A ll t h at w as st at ed i n the r ec o rd

— b y cou ns el, not th e cou rt

— w as th at“ ev ery th i ngi s wai ve d w ith th e ex ce pti o n o fthe reason ablen ess of the sen ten ce,” and t ha t Sm ith “can ’t w i th d ra w hi s pl ea. ” The di str i ct c ourt, wh i ch bas ed on i ts o wn co m m en ts a ppar en tly ha d no t r ev i ewe d the ter m s o ft he appel l ate waive r, di d not e xplain the substa nce o fthe w ai verto S m i th, as Rule 11 ( b) ( 1) ( N ) r equi re s. The Rule does not re quir e a d et ail ed descr i pti on

— a st at ementtha t m ade i t cl ea r S m i thwas g i vingup an y ri ght he m i ght ha ve t o app ealdeci si ons the c ourthad m ade, hi s co nvi cti on, and hi s s entence would have suffi ced

—b u t t h e c ou rtga ve Sm ith n o e x p lan at ion atall. The cour t’ s f ai l ure to provi de Sm i th anyexpl anati on o r descri pti on of the appell ate w ai ver w as not cured by its vague questi on t o Sm i th, “You underst and that?” “That” i s m os t reaso nabl y unders too d as r efer ring to wh at Sm ith ’ s c o u n se l ha d j u st sa id

— that Sm i th had ag re ed h e “ c an ’t w i th d ra w h is p lea .” W e c an n otrea so n ab lyN o. 09

- 1443 17

con clud e from this briefex ch an ge th at Sm ith un d erstood , or even said h e un d erstood , the ap p ell ate w aiver. N ot eve rydevi ati on fro m Rule 11 ( b) ’ s r equi re m ents re nd er s a n appell ate waiver unenfo rce abl e. In thi s ca se, how eve r, the re cor d ofthe ple a co l l oquy does not r efl ec t th atS m i thunde r st o o d th e a ppel l at e r i g ht s he w as gi vi ngu p. Mo r e t o the p o i nt, the r e c o r d d o e s n ot re flec t a n u n d er st an d i n g t h a t Sm ith w as giv in g u p h is rig h t t o a p p e a l f ro m th e d ist ric t c ou rt ’s d en ial of h is defe nse c ounselo fchoi ce. Given the cour t’ s f ai l ure to m eetthe re quir em ents ofRule 11 (b )(1) ( N ) and the fund am en ta lna tu r e o fthe unde r l y i ngr i g hta t i ss ue , the pl e a a g r e e men t ’ s a pp e l l a t e wa i v e r do e s no t pr ec l ud e Sm ith from cha ll en ging on d irect app eal the cou rt’s al l ege d denialo fhi s r i ght t o counselo fhi s cho i ce.
B. D enia l ofChoice ofCoun sel Turningto the m er i ts, we c on c l ud e that S m i th was den i ed hi s S i xth Am end m en t r i g htt o hi s ch o i ce o fc o unse l

. The S i xth Am en dm en t “ guar an te es a de fen dan t th e ri ght t o be r epres ented byan o ther w i se quali fi ed att or ney w hom thatdefendant can a ff or d to h ire .
. . . ” Capl i n & D rysd a le, Ch a rtered v. U nited Sta tes , 491 U
. S. 617, 624 (1989 ). The const i tuti on “ com m an d s . . . thatthe accused be d efe n d ed by th e c ou n se l he be liev es to be th e b e s t .” G o nz a lez -Lo pez , 54 8 U.S
. at14 6. Thi s r i g ht, o f co ur se , i s no t wi th o utl i m i ts
. Am o ng othe r thi ngs, tr i alcou rt s have the a uthor i ty to est abl i sh cr i te r i a f o r a dm i tt i ngl awy er s to pra ct i ce , and a de fen dan t18 N o. 09

- 1443

m ay not dem and that a courth onorh i s w ai vero fco nfl i ctfre e re p re se n ta tio n . Se ei d. at 151- 52 ( ci ti ng Whea t v. U nited Sta tes , 48 6 U.S
. 1 53 , 1 59- 60 ( 1988 ) )
. Court s a l so have an int er es t in en su rin g t h at tria ls “a re co n d u c te d w ith in the ethi calst andards o fthe profess i on a nd thatl ega l proce edi ngs a p p ea r f ai r to al lwh o obs er ve them

. ” Whe at, 48 6 U. S
. a t 16 0 ( quo te d i n G o nz a lez -Lo pez , 548 U
. S. at 152)). Mo r e d i r e c t l y p e r t i n e n tt o S mi th ’ s c a s e , th e S u p r e me C ou rth as “re c og n ize d a tr ial c ou rt ’ s w i d e la tit u d e in b a l a nc i ngthe r i g htt o c o un s e lo fc ho i c e a g a i ns tthe nee ds of fa irn es s a n d ag ain st th e d em an d s o f its ca l en d ar .” G o nz a lez -Lo pez , 548 U
. S. at 152 (citations om it t ed ). The re cor d i n thi s c as e, however, does notsupport a con ten tion th at th e d em an d s o f th e d istri ct cou rt’s c a l e nd a r j us t i fi e d de ny i ng S mi th’ s r e qu e s t t o have Bri nd l ey re prese nt hi m . The di str i ct c ourt based i ts rul i ng en tir ely on i ts deter m i nati on t o tr y the cas e o n N ov em b er 4, 20 08 , a d at e o n w h ich B rin d ley w as u n av ailabl e due to a previ ousl y- settrialdate i n another cour t. B u tth e r e c o r d r e fl e c t s t h a tt h e c o u r th a d n o ts e ta N o v e mber4 tr i aldate, o r f ort h at m att erany tr i aldate, pri or to Bri nd l ey’ s appearance i n cour t on the m oti on to s ubsti tute. The tr i aldate w as not setunti lthe date Bri nd l ey appeared

— aft er th e m ot ion t o s u b st itu te h is a p p e a r an ce ha d b e e n o n fi l e f o r t wo we e k s . ( As we ha v e i n d i c a t e d , th e g o v e r n me n t s t a t e d a t o r a la r g um ent b ef or e us that pri orto the hearin g on the m oti on to su b st itu te , no tria l d at e h ad be en se t.) W e al s o n o t e th a tb a s e d o n th e r e c o r d , th e r e i s s o me questi on wh etherthe d istri ct c ourtco rr ectly unders too dN o. 09

- 1443 19 th e s c o p e o fS mi th ’ s r i g h tt o c o u n s e lo fh i s c h o i c e . As quoted ear l i er, after Bri nd l ey ar gued that “M r. Sm i th ha s a con stitut ional ri gh t t o choice of coun sel, ” the cou rt r epl i ed, “ N o , he do es no t. He h ad a co ns ti tu ti o na lr i g ht to counsel. H e doe sn’ t hav e a co nsti tuti onalr i ght t o pickany perso n he wanted. ” S ept . 8 , 2008 Tr. 7. That st atem en t i s i nc o ns i st en t wi th G o nz a lez -Lo pez and i ts Suprem e Cour t for ebea rs . Though the cour t fol l owed th is w ith a st at em en t a llu d in g t o t h e c ou rt ’s s c h ed u le and counsel ’ s a vai l abi l i ty, the cour t’s com m ents, ta ken as a w hole, refl ect th at it did n ot give sufficient con side rat i o n t o S m i th ’ s S i xth Am en dm en t r i g htto ret ain the counselo fhi s cho i ce. The re cor d al so m ake s cl earthatthe dist ri ct c ourtw as u n w illing to en te rt ain an y s or t o f a c on tin u a n c e a t a ll. Speci fi cally, t h e courtst ate d that “ thi s ca se i s g oi ng to tr i al N ove m ber 4th. I t i s not a subj ect f or disc us sio n o r a t opi c up f ordebate

. ” S ep t. 8, 20 08 Tr. 8. W hen Brin dl eya tt empte d t o b r i ngup th e to pi c ag ain, the cour t decl i ned to c on si der i t, sa yi ng tha t “ [ y] ou’ re not inth is c as e” an d th at “I’ll ta lk to h im [Sm ith ] ab ou t t h at .” Id. a t 11
. ButwhenBr i ndl eyf o l l ow ed up b y a sk i ngthe cour t t o i nquir e o fS m i th, the cour t di d not do so, tel l i ng Brind l ey, “You a re excuse d.” Id. Ad he r en ce t o a t r i alda te o nc e se t i s a wor thy g o al, b ut a d istri ct cou rt’s sche d ule, th ou g h a significant cons iderati on, does notauto m atical l y t rum p al lo theri nter est s. See U nited Sta tes v. M iller, 327 F.3d 598 , 6 0 1 ( 7 t h C ir. 2003 )
. In thi s ca se, no tr i aldate had been s et pri orto Bri nd l ey’ s a pp ear ance o n the m oti on t o su b st i tute. Fo r20 N o. 09

- 1443

Althougha defen dantwho ha s be enim pro per l y de ni ed the 2 counsel ofh is choice need not s how prej ud ic e, w e note that Sm ith p led gui l t y ( i n a c as e thatha d bee n pe ndi ng for ne a r l y e i gh t e e n m on ths ) a m e r e thr e e we e ks a ft e r Br i nd l ey w as d en ied p erm ission to sub stitute, Sm ith’s en suin g requ est to r ei nst ate his origi nal att orney w as overruled, and ap pointed c o u n s e l w a s f o r c e d u p o n h i m. th is r eason , all ow ing him to s u b stitut e as Sm ith’s counselw ou l d not hav e a dvers el y i m pacted any date th e cou rt had prev iously set. T he cou rt’s des ire to try the c ase o n N ove m ber4 does not j usti fy its d eni alo f Sm i th’ s r i ght t o counselo fhi s cho i ce. W e a l so r ej ect the g ove rnm ent’ s a rgum ent that S m i th w as tr yi ng to m ani pu l ate the sched u le by s eek i ng to substi tute Bri nd l ey’ s app ear ance. Thi s a rgum ent l acks a nys up po r ti n the r e c o r d. Ag a i n, n o t r i a lda t e h a d b een s e tp r i o r t o t he h e a r i n go nth e mo t i o n t o s u b s t i t u t e . As a r esul t, ther e is no bas i s t o concl ud e that S m i th was tr yi ng to st al lthe dispos i ti on o fthe case . W e fi nd thatthe dist ri ct cou rt er ro neousl y deni ed Sm i th hi s co nsti tuti onalr i ght t o hi s cho i ce ofdefense co uns el

. Und er G o nz a lez -Lo pez , S m i th i s no t r equi re d to p ro ve th at h e w as p rej u d ice d by th e v iola tio n . H e is 2 e nt i t l e d t o h a v e h i s g ui l t y p l e a v a c a t e d.

III. C ON CLU SI ON Forthe f or ego i ng reas ons, we vacat e S m i th’ s co nvi cti on an d sen ten ce and rem an d his case to th e d istri ct c o u rtN o. 09

- 1443 21

w i th i nstr ucti ons to perm i t S m i th to w i thdraw his gui l ty p lea . The g ove rnm ent’ s m oti on t o dism i ss the a pp eal i s de ni e d. Ci r c ui tR ul e 3 6 s ha l la pp l y o n r e man d.

8- 19- 10