# U ni te d S ta te s Co ur t of A pp ea ls

For the Eig hth Circu it

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No. 1 6- 40 08

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Uni te d S ta te s o f Am eri ca

ll ll ll ll ll ll ll ll ll ll l Pla in ti

ff - App el le e

v.

Ro be rt C arl Sh arp

ll ll ll ll ll ll ll ll ll ll l Defe nd

an t - Ap pe ll an t

__ __ __ __ __ __

App eal fro m

Uni te d S ta te s Di st ric t Co ur t

fo r th e Nor th ern Dis tri ct of I owa - Ced ar Ra pi ds

__ __ __ __ __ __

Su bm it te d: Sep te m

be r 21 , 20 17

Fil ed : J an ua ry

5, 2 01 8

__ __ __ __ __ __

Befo re SM ITH, Chi ef J ud ge , W OLLMAN and GRUENDER, Circu it Ju dg es

.

__ __ __ __ __ __

GRUENDER, Circ ui t J ud ge

.

Ro be rt Carl Sh arp pl ead ed gu il ty aft er a gr an d jury ret ur ne d a th ree- co un t

su pe rs ed in g in di ct m en t ch arg in g hi m wit h (1 ) co ns pi racy to m an uf act ur e an d

di st rib ut e a co nt ro ll ed su bs ta nc e, in vi ol at io n of 21 U.S.C. § 84 6; (2 ) po ss es si on wit h

in te nt to di st rib ut e a co nt ro ll ed su bs ta nc e, in vi ol at io n of 21 U.S.C. § 84 1( a)(1 ); an d

(3 ) po ss es si on wit h in te nt to di st rib ut e, an d a id in g a nd ab et ti ng th e po ss es si on wit hin te nt to di st rib ut e, a co nt ro ll ed su bs ta nc e, in vi ol a t i o n of 21 U.S.C. § 84 1( a)(1 ).

S h arp su bs eq ue nt ly fil ed a m ot io n to wit hd raw hi s gu il ty pl ea. The di st ri c t c o u r t 1

de ni ed th e m ot io n an d se nt en ced Sh arp to th irt y y ears ’ im pr i s o nm en t. He no w

ap pe al s th e jud gm en t, arg ui ng th at th e di st ric t co ur t ab us ed it s di sc ret io n in de nyin g

th e m ot io n a nd th at it pl ai nl y erre d in fai li ng to reco ns id er the m ot io n su a sp on te in

li gh t of ev id en ce pr es en te d at th e se nt en ci ng he ari ng

. Fo r th e reas on s th at fo ll ow, we

affi rm

.

I.

In 20 12

, Sh arp was rel eas ed fro m fed eral pr is on aft er se rv in g a s e n t e n c e fo r

po ss es si on wit h in te nt to di st rib ut e co cai ne ba se

. W hi le on su pe rv is ed rel eas e, he

be ga n m an uf

act ur in g an d se ll in g synth et ic can na bi no id s in Ill in oi s an d th en Io wa.

Sh arp pu rch as ed synth et ic -can na bi no id ch e mi c a ls in bu lk fro m va rio us

su pp li ers

, an d he an d hi s em pl oyee wou ld ap pl y th em to le afy s u b s t a n c e s

. The y

wou ld t h e n pa ck ag e an d la be l th es e “ he rb al in cen se ” pr od uc ts fo r sa le

. The

pa ck ag in g in cl ud ed a warn in g th at th e pr od uc ts were no t fit fo r hu m an co ns um pt io n,

ev en th ou gh Sh arp kn ew th at cu s t o mer s wou ld sm ok e th em

. Sh arp ad m it te d to

kn owi ng th at hi s pr od uc ts cau se d “ di so rie nt a t i o n ” a n d ha d “ no ot he r go od us e,”

al th ou gh he ad de d th at th ey di d no t pr od uc e “a e u p h o ric hi gh ” li ke m ari juan a.

Not ab ly, Sh a r p p ai d hi s em pl oyee in cas h, an d hi s em ai ls or de rin g a ch em ic al he

cal le d “ THJ-0 11 ” in cl ud ed th e h ead in g “ AB-FUBI NACA.”

Acco rd in g to Sh arp

, he an d an ot he r in cen se de al er na m ed Had i Sh arai ri hi red

at to rn ey Jo el Sch wart z fo r ad vi ce ab ou t wha t pr od uc ts were le ga l to se ll an d to en su re

The Hon or ab le Lin da R. Rea de

, Uni te d St at es Dis tri ct Ju dg e fo r th e Nor th ern 1

Dis tri ct of Io wa, ad op ti ng th e rep or t an d reco m m en da ti on of th e Hon or ab le Jo n St ua rt

Sco le s, Uni te d St at es Mag is tra te Ju dg e fo r th e Nor th ern Dis tri ct of Io wa, no w ret ire d.

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-th at th ey co m pl ie d wit h al l fed eral an d st at e la ws

. Sh arp al so st at ed th at Sch wart z

fai le d to warn hi m th at th e go ve r n men t ha d sc he du le d AB-FUBI NACA as a

co nt ro ll ed su bs ta nc e. Sh arp sa i d t h a t he in fo rm ed Sch wart z of th is ov ers ig ht an d

co m pl ie d wit h Sch wa r t z ’s i n st ru ct io n to di sp os e of al l pr od uc ts th at co nt ai ne d th e

ch em ic al

. Sh arp al so cl ai m ed th at he se nt Sch wart z a sa m pl e of a su bs ta nc e th at he

be li ev ed was THJ-0 11 fo r te st in g al on g wit h a $9 00 m on ey or de r. Sh arp m ai nt ai ne d

th at whe n he as ke d fo r th e res ul ts

, Sch wart z res po nd ed “ th at he co ul d no lo ng er ha ve

pr od uc ts tes te d.”

Sch wart z’s reco ll ect io n of th e at to rn ey -cl ie nt rel at io ns hi p di ffer ed

. Dur in g th e

he ari ng on Sh arp ’s m ot io n to wit hd raw hi s gu il ty pl ea, Sch wart z te st ifi ed th at Sh arp

so ug ht rep res en ta ti on “ fo r a po te nt ia l fu tu re cri m in al cas e” aft er a pr ev io us en co un te r

wit h la w en fo rcem en t— no t ad vi ce a b o u t h o w to se ll synth et ic dr ug s le ga ll y

.

Sch wart z ex pl ai ne d t ha t h e warn ed Sh arp “ th at ev erythi ng synth et ic al ly tha t ca us es

im pa irment of th e br ai n ei th er w a s l i s t e d or was an an al og or wou ld be so on

th erea fte r.” As a res ul t, he in fo rm ed Sh arp th at “ if he were ch arg ed wit h so m et hi ng

,

he wou ld be a care er of

fen de r an d th is was to o da ng ero us a ga m e fo r hi m to pl ay an d

he sh ou ld st op .”

Non e t he le ss

, Sch wart z ack no wled ge d th at he di d of fer Sh arp ad vi ce on

whe th er cert ai n su bs ta nc es were le ga l. In pa rti cu la r, in res po ns e to a qu ery fro m

Sh arp

, Sch wart z se arch ed fo r THJ -0 11 on th e web si te of th e Dru g Enfo rcem en t

Age nc y an d on Goo gl e. Alt ho ug h he di d no t fin d an y th in g in di cat in g th at it was

il le ga l, he d id no t i nf

or m Sh arp th at th e su bs ta nc e was th eref or e le ga l. And th ou gh

Sch wart z co ul d no t reca ll sp eci fic al ly ad vi si ng Sh arp th at it was il le ga l, he

ne ve rth el es s warn ed hi m th at “ ev erythi ng th at ’s se ll in g as synth et ic s ei th er is no w or

w i l l s o on be il le ga l on ce th e Gov ern m en t fin ds th at y ou ha ve it .” Sch wart z al so

ad vi se d Sh arp th at he was vi ol at in g FDA reg ul at io ns by se ll in g m is br an de d pr od uc ts

.

In ad di ti on

, Sch wart z te st if i e d t h a t h e ha d no reco ll ect io n of Sh arp gi vi ng hi m a

-3

-sa m

pl e fo r te st in g an d th at

, if Sh arp ha d, he wou ld ha ve de st ro y ed it be cau se “ I’m no t

go in g t o h av e so m et hi ng th at m ig ht be an il le ga l n arco ti c in m y off ic e.”

In e arl y 20 14

, la w en fo rcem en t be ga n in ve st ig at in g Sh arp ’s act iv it ie s.

I n v e s ti ga to rs se nt a co nf id en ti al so ur ce to m ak e pu rch as es at Sh arp ’s st or e

. A n

em pl oyee to ld th e so ur ce th at Sh arp was no t in an d “ pr ob ab ly to ok [th e he rb al

in cen se ] wit h hi m .” The em pl oyee sa id th at

, w i t h “ rai ds ha pp en in g ev eryw he re,”

Sh arp was “

jus t be in g sm art .” A su bs eq ue nt co nt ro ll ed pu rch as e pr ov id ed pr ob ab le

cau se th at Sh arp was se ll in g co nt ro ll e d s u b s ta nc es

, an d la w en fo rcem en t of fic ers

ex ecu te d se arch warra nt s on hi s res id en ce, hi s ve hi cl e, a st or ag e un it th at he acq ui red

un de r a fal se na m e, an d h is em pl oyee’s res id en ce. The y fo un d pro du ct s con ta in in g

AB-FUBI NACA, whi ch is a Sch ed ul e I co nt ro ll ed su bs ta nc e, as well as $ 88 ,66 3 i n

cas h p ro ceed s from th e can na bi no id s. The gr an d jury th en ret ur ne d t he th ree- co un t

su pe rs ed in g i nd ic tm en t.

Ju st be fo re tri al was to be gi n, Sh arp pl ead ed gu il ty to al l th ree co un ts wit ho ut

a pl ea ag reem en t. Dur in g th e pl ea co ll oq uy, Sh arp ad m it te d hi s in vo lv em en t in an d

kn owl ed ge of a co ns pi racy to m an uf act ur e an d di st rib ut e AB-FUBI NACA (Co un t 1)

.

Fo r th e po ss es si on wit h in te nt to di st rib ut e co un ts (Co un ts 2 an d 3)

, ho wev er, Sh arp

in si st ed th at he th ou gh t th at he was d i s t r i b u t in g THJ-0 11 rat he r th an ABFUBINACA. Nev ert he le ss

, he pl ead ed gu il ty to Co un ts 2 a n d 3 u nd er a th eo ry of

wil lfu l bl in dn es s. Se e Glo ba l-T ech App li an ces

, In c. v. SEB S.A.

, 56 3 U.S. 75 4, 76 9

(2 01 1)

.

In Decem be r 20 15

, Sh arp ret a i n e d ne w co un se l an d m ov ed to wit hd raw hi s

gu il ty pl ea. Fo ll owi ng an ev id en ti ary he ari ng at whi ch bo t h S h a r p an d Sch wart z

te st ifi ed

, th e m ag is t r at e jud ge is su ed a rep or t an d reco m m en da ti on co nc lu di ng th at

Sh arp ’s m ot io n sh ou ld be de ni e d

. The di st ric t co ur t ov erru le d Sh arp ’s ob jecti on s,

ad op te d th e m ag is tra te jud ge ’s rep or t an d reco m m en da ti on

, an d de ni ed Sh arp ’s

-4

-m ot io n to wit h d r a w hi s gu il ty pl ea. Fo ll owi ng an ev id en ti ary he ari ng

, Sh arp was 2

se nt en ced to th irt y

y ears ’ im pr is on m en t.

II

.

W e rev ie w th e de ni al o f a mo t io n to wit hd raw a gu il ty pl ea fo r an ab us e of

di sc ret io n. Uni te d St at es v. Van Dor en

, 80 0 F

. 3d 99 8, 10 01 (8 th Ci r. 20 15 ). A

de fen da nt m ay wit hd raw a pl ea of gu il ty be fo re th e co ur t im po se s a se nt en ce if “ th e

de fen da nt can sh ow a fai r an d jus t reas on fo r req ue st in g t h e w it hd rawal .” Fed

. R.

Cri m

. P. 11 (d )(2 )(B)

. “ W hi le th e st an da rd is li be ral

, th e de fen da nt ha s no au to m at ic

rig ht to wit hd raw a pl ea.” Uni te d St at es v. Heid

, 65 1 F.3 d 85 0, 85 3 (8 th Ci r. 20 11 ).

A de fen da nt be ars th e bu rd en of es ta bl is hi ng a fai r an d jus t reas on

. Uni te d St at es v.

Cr uz

, 64 3 F.3 d 63 9, 64 2 (8 th Ci r. 20 11 ). W e co nc lu de th at th e di st ric t co ur t di d no t

ab us e it s d is cret io n i n d en y in g S ha rp ’s m ot io n t o wi th dr aw hi s g ui lt y pl ea.

A. Confl ic t of

int eres t an d in effe cti ve as si st an ce o f co uns el

Sh arp fir st arg ue s th at th e di st ri c t c o u r t ab us ed it s di sc ret io n in refu si ng to

al lo w hi m to wit hd raw hi s gu il ty pl ea be cau se hi s la wy er ha d a co nf li ct of in te res t an d

pr ov id ed hi m in effe ct iv e as s i s t a n c e of co un se l. In pa rti cu la r, Sh arp arg ue s th at

Sch wart z h ad a co nf

li ct of i nt eres t b ecau se he was a vi ta l fa ct wit ne ss as t o S ha rp ’s

men s re a

. Se e Uni te d S t a t e s v

. M er li no

, 34 9 F.3 d 14 4, 15 2 (3 rd Ci r. 20 03 )

(ex pl ai ni ng th at th e po ss ib il it y of c o u n s e l’s “ be in g cal le d as a wit ne ss was a

. . .

so ur ce of po te nt ia l co nf

li ct

, as it is of

te n im pe rm is si bl e fo r an at to rn ey to be bo th an

a d v o c a t e an d a wit ne ss ”). In th is ci rcu it

, it is un cl ear whe th er th is so rt of al le ge d

co nf li ct of in te res t req ui res a de fen da nt to sh ow de fic ie nt pe rfo rm an ce an d pr ejud ic e

At t he he ari ng , Ha di Sh arai ri te st ifi ed ab ou t a le tt er Sh arp wrot e u rg in g h im 2

to m ak e fal se st at em en ts

. In ad di ti o n

, S h a rp in tro du ced reco rd in gs of se ve ral

co nv ers at io ns he ha d wi th Sch wart z whe n S ha rp was i n jai l awa it in g t ria l.

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-un de r St ri ckl an d v. W as hi ng to n

, 46 6 U.S. 66 8, 68 7 (1 98 4)

, or whe th er it is su ffi ci en t

fo r a de fen da nt to sh ow th at a co nf li ct of in te res t “ad ve rs el y affe ct ed hi s la wy er’s

pe rfo rm an ce,” s e e C

a b a n v. Uni te d St at es

, 28 1 F.3 d 77 8, 78 1- 84 (8 th Ci r. 20 02 )

(q uo ti ng Cu

yl er v. Su ll iv an

, 44 6 U.S. 33 5, 34 8 (1 98 0) ). W e ne ed no t ch oo se be twee n

th e St ri ckl an d an d Cu

yl er st an da rd s b ecau se Sh arp ’s cla im fai ls un de r bo th

.

Und er Cu yl er

, Sh arp m

us t id en ti fy “ so m e act ua l an d de m on st rab le a d ve rs e

effe ct on th e cas e, no t m erel y an ab st ract or th eo ret ic al on e.” Se e Co v e y v

. Uni te d

St at es

, 37 7 F.3 d 90 3, 90 8 (8 th Ci r. 20 04 ). He m us t sh ow th at “ th e co nf

li ct cau se d th e

at to rn ey ’s c ho ic e.” Se e id

. Acco rd in g to Sh arp , S ch wart z co ul d ha ve te st ifi e d th at

Sh arp th ou gh t th e su bs ta nc e was THJ-0 11 an d th at he in ve st ig at ed whe th er it was on

th e dr ug sc he du le s. Sh arp m ai nt ai ns th at Sch wart z’s t e s t i mo ny wou ld ha ve

es ta bl is he d th at he di d no t sa ti sf y th e tw o el em en ts of wil lfu l bl in dn es s: “ (1 ) th e

de fen da nt m

us t su bjec ti ve ly be li ev e th at th ere is a hi gh pr ob ab il it y th at a fact ex is ts

an d (2 ) th e de fen da nt m

us t ta ke de li be rat e act io ns t o a v o i d l e arn in g of th at fact .”

Glo ba l-T ech , 56 3 U.S. at 76 9; se e a ls o Un it ed St at es v. Han se n , 7 91 F.3 d 8 63 , 86 8

( 8 t h Ci r. 20 15 ) (“ [T]he jury m ay fin d wil lfu l bl in dn es s on ly if th e de fen da nt w a s

aware of fact s th at pu t hi m on no ti ce th at cri m in al act iv it y was pr o b a b l y afo ot an d

de li be rat el y fai le d to m ak e fu rth er in qu iri es

, in te nd in g to rem ai n ig no ran t.”)

. Had he

real iz ed th at Sch wart z was a po te nt ia l witn es s, Shar p clai m s he wou ld ha ve go ne to

tri al in st ead of p le ad in g g ui lt y

.

As th e Su pr em e Co ur t ha s ex pl ai n e d

, th e Gov ern m en t can pr ov e kn owl ed ge

un de r 21 U.S.C. § 8 41 (a) t hr ou gh eit he r di rect or c irc um st an ti al ev id en ce:

Dire ct ev id en ce co ul d in cl ud e, fo r ex am pl e, pa st arre st s t ha t pu t a

de fen da nt on no ti ce of th e co nt ro ll ed st at us of a su bs ta nc e.

Ci rcu m st an ti al e v i d e nc e co ul d in cl ud e, fo r ex am pl e, a de fen da nt ’s

co nc eal m en t of hi s act iv it ie s, e v a s i v e be ha vi or wit h res pe ct to la w

-6

-en f

o r cem en t, [an d] kn owl ed ge th at a pa rti cu la r su bs ta nc e pr od uc es a

“ hi gh ” si m il ar t o t ha t p ro du ced by con tro ll ed su bs ta nc es

. . . .

McFad de n v . Uni te d S ta te s , 13 5 S . Ct. 2 29 8, 2 30 4 n .1 (2 01 5) (ci ta ti on om it te d)

.

In as m uc h as Sch wart z’s te st im on y w o u l d ha ve pr ob at iv e va lu e un de r th is

st an da rd

, Sh arp ha s no t sh own th at su ch a st rat eg y wou ld ha ve be en “ ob jecti ve ly

reas on ab le un de r th e fact s of th is cas e,” nor ha s he sh own th at Sch wart z’s ad vi ce to

pl e a d g u il ty “ was li nk ed to th e act ua l co nf li ct .” Se e Co vey

, 37 7 F.3 d at 90 8.

Sch wart z reas on ab ly ex pe ct ed th at th e Gov ern m en t co ul d pr ov e be y on d a reas on ab le

do ub t th at Sh arp kn owi ng ly po ss es se d a co nt ro ll ed su bs ta nc e. In de ed

, in hi s

te st im on y at th e p l e a wit hd rawal he ari ng

, Sch wart z m en ti on ed th e un de rco ve r

pu rch as e at te m

pt whe re Sharp ’s em

pl oyee st at ed th at Sh arp to ok th e he rb al in cen se

ou t of th e st or e at ni gh t; Sh arp ’s em ai ls or de rin g THJ-0 11 un de r th e he ad in g of ABFUBINA C A ; th e al ia s Sh arp us ed to pu rch as e a st or ag e lo ck er fo r th e in cen se ; hi s

pa y in g hi s em

pl oyee in cas h; an d hi s la be li ng th e in cen se as no t fo r hu m an

co ns um pt io n ev en th ou gh Sh arp kn ew hi s cu st om ers were sm ok in g it

. In ad di ti o n

,

Sh arp kn ew th at th e su bs ta nc e ha d a di so rie nt in g effe ct

, an d hi s pr io r dr ug co nv ic ti on

de m on st rat es so m e fam il ia rit y wit h th e dr ug la ws. Mo reo ve r, ha d Sch wart z te st ifi ed

,

he wou ld ha ve ex pl ai ne d th at he to ld Sh arp th at synth et ic dr ug s were ei th er il le ga l or

wou ld so on be cl as si fie d as il le ga l. He al so wou ld ha ve st at ed th at he to ld Sh arp th at

th is bu si ne ss was “ to o da ng e r o u s ” a n d th at Sh arp sh ou ld st op

. If an y th in g, su ch 3

Sh arp ’s fai lu re to he ed Sch wart z’s in st ru ct io n to st op se ll in g synth e ti c 3

can na bi no id s al so pr ecl ud es S c h w a r t z ’s te st im on y as pa rt of an ad vi ce-o f-co un se l

de fen se st rat eg y

. To rel y up on an ad vi ce-o f-co un se l de fen se

, a de fen da nt m us t sh ow

th at he “ (i) fu ll y di sc lo se d al l m at eri al fact s to hi s at to rn ey be fo re se ek in g ad vi ce; an d

(ii ) act ua ll y rel ie d on hi s co un se l’s ad vi ce in th e go od fai th be li ef th at hi s co nd uc t was

le ga l.” Uni te d St at es v

. Rice

, 44 9 F.3 d 88 7, 89 7 (8 th Ci r. 20 06 ). Eve n as su m in g

Sh arp sa ti sf

ie d th e fir st el em en t, Sch w a r t z ’s te st im on y es ta bl is he s th at he fai le d to

sa ti sf y th e se co nd ele m en t.

-7

-te st im on y wou ld bu rn is h th e Gov ern m en t’s cas e th at Sh arp di d kn ow th at hi s pr od uc t

was il le ga l. Giv en th es e fact s, th e al le ge d co nf li ct di d no t ad ve rs el y affe ct Sch wart z’s

pe rfo rm an ce in ad vi si ng Sh arp to pl ead gu il ty. Fo r th e sa m e reas on s, Sh arp al so fai ls

to es ta bl is h de fic i e n t p e r fo rm an ce an d pr ejud ic e un de r St ri ckl an d ’s m or e st rin ge nt

st an da rd

. Se e 46 6 U.S. at 68 7; se e al so Hil l v. L o c k

h a r t

, 47 4 U.S. 52

, 59 (1 98 5)

(ex pl ai ni ng th at th ere is pr ejud ic e un de r St ri ckl an d whe n, bu t fo r co un se l’s erro rs

,

de fen da nt wou ld no t ha ve pl ead ed gu il ty an d wou ld ha ve in si st ed on go in g to tri al ).

In ad di ti on to al le gi ng th at Sch wart z h a d a co nf li ct of in te res t, Sh arp fu rth er

arg ue s th at Sch w a r t z pr ov id ed in effe ct iv e as si st an ce of co un se l be cau se Sch wart z

m is in fo rm ed hi m ab ou t wil l fu l bl in dn es s. Fo r th is se co nd cl ai m

, Sh arp m us t sh ow

bo th de fic ie nt pe rfo rm an ce an d pr ejud ic e. Se e St ri ckl an d

, 46 6 U.S. at 68 7. He arg ue s

th at Sch wart z in co rrec tl y ad vi se d hi m th at he was wil lfu ll y bl in d mer el y be cau se he

di d no t hav e th e ch em ic al tes te d. Sh arp po in ts ou t t ha t tes ti ng m ay no t hav e be en a

real is ti c op ti on be cau se m os t la bo ra t o r i es wou ld no t acce pt po te nt ia ll y il le ga l

su bs ta nc es

.

In l i g ht of th e ev id en ce ag ai ns t Sh arp

, Sch wart z’s ad vi ce co nc ern in g wil lfu l

bl in dn es s was ne it he r de fic ie nt no r pr ejud ic ia l. Sh arp pr of es se d hi s ig no ran ce of th e

tru e id en ti ty of THJ-0 11 ev en th ou gh Sch w a r t z ’s reas on ab le as se ss m en t of th e

ev id en ce in di cat ed th at th e Gov ern m en t wou ld be ab le to pr ov e hi s ac tu al kn owl ed ge

be y on d a reas on ab le do ub t. N o n et he le ss

, in th e face of Sh arp ’s in si st en ce th at he

th ou gh t th e ch em ic al was THJ-0 11

, Sch wart z reas on ab ly co nc lu de d th at t h e

Gov ern m en t co ul d al so es ta bl i s h Sh arp ’s men s re a un de r a th eo ry of wil lfu l

bl in dn es s. Se e Glo ba l-T

ech , 56 3 U.S. at 76 9 (“ [A] w il lfu ll y bl in d de fen da nt is on e

who

. . . can al m os t be sa id to ha ve act ua ll y kn own th e cri ti cal fact s.”) ; Uni te d St at es

v. Gal ima h

, 75 8 F.3d 92 8, 9 31 (8t h C ir. 2 01 4) (“ A de li be rat e ig no ran ce or a wil lfu l

bl in dn es s in st ru ct io n is a m ech an is m fo r in fere nc e, no t a su bs ti tu te fo r kn owl ed ge .”

(in te rn al qu ot at io n m ark s o m it te d) ).

-8

-Des pi te th e Gov ern m en t’s st ro ng cas e, Sh arp m ig ht ha ve be en ab le to refu te th e

in fere nc e th at he ha d th e req ui si te kn owl ed ge if a rep ut ab l e l a b ha d te st ed th e

su bs ta nc e. Cf

. Uni te d St at es v. Mak

ka r

, 81 0 F.3 d 11 3 9

, 11 47 -4 8 (1 0t h Ci r. 20 15 )

(ex pl ai ni ng th at ev id en ce th at de fen da nt s as ke d st at e la w en fo rcem en t ag en ts to te st

th e in cen se th ey were se ll in g was rel ev an t to men s re a ). Howev er, hi s fai lu re to ha ve

th e s u b s t a n c e t es te d m ad e it al m os t im po ss ib le fo r hi m to reb ut th e Gov ern m en t’s

cas e. In ot h e r wor ds

, th e m ere fai lu re to te st was no t en ou gh to es ta bl is h wil lfu l

bl in dn es s, bu t Sh arp ’s fai lu re to ha ve th e su bs ta nc e te st e d i n t h e face of su ch

ov erwh el m in g e vi de nc e in di cat ed th at he was

, at th e ve ry lea st , “ bu ry in g [h is ] he ad

in th e s a n d.” Se e Uni te d St at es v. Flo re z

, 36 8 F.3 d 10 42

, 10 44 (8 th Ci r. 20 04 )

(“ Ig no ran ce is de li be rat e if th e d efen da nt was pr es en te d wit h fact s th at pu t he r on

no ti ce th at cri m in al act iv it y was pa rti cu la rly li ke ly an d y et sh e in te nt io na ll y fai le d to

in ve st ig at e th os e facts .”). As a res ul t, Sch wart z’s ad vi ce co nc ern in g wil lfu l bl in dn es s

was no t de fic ie nt an d di d no t pr ejud ic e Sh arp

. Se e Eva ns v. Lu eb be rs

, 37 1 F.3 d 43 8,

44 5 (8 th Ci r. 20 04 ) (“ [S]trat eg ic an d ta ct ic al de ci si on s m ad e by co un se l, th ou gh th ey

m ay ap pe ar un wis e in hi nd si gh t, can n o t s e r ve as th e ba si s fo r an

in effe ct iv e-as si st an ce cl ai m un de r St ri ckl an d .”).

Fo r al l th es e reas on s, the di st ric t cou rt di d no t ab us e it s di sc ret io n in refu si ng

to all ow h im

to wit hd raw h is gu il ty ple a.

B. Fact ua l ba si s fo r g ui lty ple a

Sh arp al so arg ue s t h a t t h e di st ric t co ur t ab us ed it s di sc ret io n in refu si ng to

al lo w hi m to wit hd raw hi s gu il ty pl ea be cau se th e pl ea l a c k s an ad eq ua te fact ua l

ba si s. Fed eral Ru le of Cri m in al Pro ced ur e 11 (b )(3 ) m an da te s th at

, “ [b ]efore en te rin g

jud gm en t on a gu il ty pl ea, th e co ur t m us t de te rm in e th at th ere is a fact ua l ba si s fo r th e

pl ea.” A de fen da nt es ta bl is he s a fai r an d jus t reas on fo r wit hd rawi ng hi s gu il ty pl ea

by de m on st rat in g th at hi s pl ea is no t su pp or te d by an ad eq ua te fact ua l ba si s. Uni te d

-9

-St at es v. Heid

, 65 1 F.3 d 85 0, 85 5- 56 (8 th Ci r. 20 11 ). “ A gu il ty pl ea is su pp or te d by

an ad eq ua te fact ua l ba si s whe n th e reco rd co nt ai ns su ffi ci en t ev id en ce at th e ti m e of

th e pl ea up on whi ch a co ur t m ay reas on ab ly de te rm in e th at th e de fen da nt li ke ly

co m m it te d th e of

fen se .” Uni te d St at es v. Ch en ey

, 57 1 F.3 d 76 4, 76 9 (8 th Ci r. 20 09 )

(in te rn al qu ot at io n m ark s om it te d)

. Bec au se t h e r e w a s no pl ea ag reem en t or

st ip ul at ed fact s, t he di st ric t co ur t re li ed on th e Gov ern m en t’s Ru le 11 let te r an d t he

pl ea co ll oq uy to d et erm in e whe th er t he re i s a s uf fic ie nt fact ua l b as is

.

The Gov ern m en t ha d to es ta bl is h th at Sh arp kn ow in gl y po ss es se d a co nt ro ll ed

s u b s t a n c e

. S ee 21 U.S.C. § 84 1( a). Sh arp ne ed ed to kn ow th at he po ss es se d a

su bs ta nc e li st ed on th e co nt ro ll ed su bs ta nc e sc he du le s, ev en if he di d no t kn ow th e

pa rti cu la r su bs ta nc e. Se e McFad de n

, 13 5 S

. C t

. at 23 04

. Alt ern at iv el y

, th e

kn owl ed ge req ui rem e n t wou ld be m et if Sh arp kn ew th e pa rti cu la r su bs ta nc e he

po ss es se d, ev en if h e d id no t k no w th at it was i ll eg al

. Se e id

.

Bu t Sh arp in si st ed th at he t h o ug ht th e su bs ta nc e was THJ-0 11

, whi ch is no t

li st ed on th e fed eral dr ug sc he du le s, an d no t AB-FUBI NACA, whi ch is li st ed

. As a

res ul t, he was un w i l l i n g t o pl ead gu il ty on ei th er of th e two gr ou nd s es ta bl is he d in

McFad de n

. In st e a d

, he pl ead ed un de r th e al te rn at iv e th eo ry of wil lfu l bl in dn es s.

D u r i n g th e pl ea co ll oq uy, th e m ag is tra te jud ge th eref or e in qu ire d whe th er he

“ be li ev ed th ere was a hi gh pr ob ab i l it y th at th e su bs ta nc e in [h is ] po ss es si on was

su bjec t to fed eral dr ug la ws an d [if he ] to ok de li be rat e a c t i o n to av oi d le arn in g th e

tru e id en ti ty of th e su bs ta nc es .” Tho ug h Sh arp an swe red affi rm at iv el y

, he no w

arg ue s th at th e reco rd la ck s a fact ua l ba si s fo r ei th er pr on g of wil lfu l bl in dn es s. Se e

Glo ba l-T ech , 56 3 U.S. at 76 9.

F i r s t

, Sh arp arg ue s th at th ere is an in su ffi ci en t fact ua l ba si s th at he be li e v e d

th at th ere was a hi gh pr ob ab il it y th at th e su bs ta nc e in hi s po ss es si on was a co nt ro ll ed

su bs ta nc e. In M

c Fa d de n

, th e Su pr em e Co ur t reject ed th e Gov ern m en t’s pr op os ed

-1 0-jury in st ru ct io n st at in g th at th e k n owl ed ge req ui rem en t wou ld be m et if th e

“ de fen da nt kn ew he was de al in g wit h an il l e g a l or reg ul at ed su bs ta nc e un de r so me

la w .” McFad

de n

, 13 5. S. Ct

. at 23 06 (em ph as is ad de d an d in te rn al qu ot at io n m ark s

om it te d)

. The Co ur t ex pl ai ne d th at Sect io n 84 1( a) in st ead “ req ui res th at a de fen da nt

kn ew he was de al in g wit h ‘a co nt ro ll ed su bs ta nc e.’ Th a t t e rm in cl ud es on ly th os e

dr ug s li st ed on th e fed eral dr ug sc he du le s or tre at ed as su c h b y o p e r at io n of th e

Ana lo gu e Act. It is no t br oa d en ou gh to in cl ud e al l su bs ta nc es reg ul at ed by an y la w.”

Id

. (ci ta ti on om it te d)

.

Dur in g th e pl ea co ll oq uy, th e m ag is tra te jud ge di d no t us e th e ph ras e

“ co nt ro ll ed su bs ta nc e ” or refe r sp eci fic al ly to th e Co nt ro ll ed Su bs ta nc es Act

(“ CSA”) , t he fed eral dr ug sc he du le s, or th e Ana lo gu e Act. In st ead , h e as ke d, “D id

y ou be l i ev e th ere was a hi gh pr ob ab il it y th at th os e—t ha t su bs ta nc e or su bs ta nc es

were su bjec t to fed eral dr ug la ws? ” Sh arp an swe red

, “ Und er so m e fed eral dr ug la w,

y es .” Bec au se th ere are fed e r al dr ug la ws be si de s th e CSA an d th e Ana lo gu e Act,

in cl ud in g fed eral la be li ng reg ul at io ns

, Sh arp arg ue s th at hi s res po ns e was to o br oa d

an d t ha t h is co nv ic ti on vi ol at es McFad de n

.

Fu rth erm or e, Sh arp m ai nt ai ns th at

, be cau se he was pr os ecu te d fo r po ss es si ng

a co nt ro ll ed su bs ta nc e un de r 21 U.S.C. § 84 1( a)— an d no t un de r th e Ana lo gu e

Act— th e Gov ern m en t m

us t m eet a st ric te r men s re a req ui rem en t. Sp eci fic al ly, Sh arp

co nt en ds th at th e Gov ern m en t m us t es ta bl is h th at he kn ew (o r was wil lfu ll y bl in d to )

th e id en ti ty of th e su bs ta nc e he po ss es se d— whi ch Sh arp ha s de nie d know ing —or th at

he kn ew (o r was wil lfu ll y bl in d to th e fact ) th at th e su bs ta nc e was on th e co nt ro ll ed

su bs ta nc e sc he du le s. Sh arp th eref or e arg ue s t h at th e Gov ern m en t can no t rel y on

ev id en ce t ha t h e be li ev ed (o r was wil lfu ll y bl in d to th e fact ) th at th e su bs ta nc e was

tre at ed a s a co nt ro ll ed su bs ta nc e by op erat io n of th e Ana lo gu e Act be cau se it was

“ su b s t a n t i al ly si m il ar” to a su bs ta nc e on th e dr ug sc he du le s. Se e 21 U.S.C.

§ 80 2( 32 )(A). In effe c t

, S ha rp m ai nt ai ns th at th e pl ea co ll oq uy wou ld ha ve be en

-1 1-in su ffi ci en t ev en if th e m ag is tra te jud ge ha d sp eci fic al ly as k e d w he th er Sh arp

be li ev ed th ere was a hi gh pr ob ab il it y th at th e su bs ta nc e in hi s po ss es si on was “ li st ed

on th e fed eral dr

ug sc he du le s or tr ea te d as su ch by op er at io n of th e Ana lo gu e Act ,”

t h e v e r y la ng ua ge pr op os ed by McFad de n

. In st ead

, Sh arp cl ai m s th at th e pl e a

co ll oq uy m

us t pr ov i d e s p e c i f

ic ev id en ce fo r hi s be li ef th at th ere was a hi gh

pr ob ab il it y

th at th e su bs ta nc e in hi s p os se ss io n was on th e fed eral dru g s ch ed ul es

.

W e di sa gr ee an d fin d an ad eq ua te fact ua l ba si s fo r th e pl ea

. F irs t, th e

m ag is tra te jud ge ’s refer en ce t o “ fed eral dru g l aws ” av oi ds th e ov erb read th co nc ern

id en ti fie d in McFad

de n

. The m ag is tra te jud ge di d no t as k Sh arp if he th ou gh t th ere

was a hi gh pr ob ab il it y th at th e su bs ta nc es were regu la te d by “ an y la w.” In st ead

, he

refe rred to “ fed eral dr ug la ws.” The m ean in g of th is ph ras e was su ffi ci en tl y cl ear in

th e co nt ex t of th e pr oc eed in g. In de ed

, i n d en y in g Sh arp ’s m ot io n to wit hd raw hi s

pl ea, th e di st ric t co ur t ex pl ai ne d th at th e wor ds “ can be un de rs to od in co nt ex t to refe r

to th e Co nt ro ll ed Su bs ta nc es Act or th e Co nt ro ll ed Su bs ta nc e Ana lo gu e Enfo rcem en t

Act of 19 86 .” Mo reo ve r, th e Su pr em e Co ur t it se lf us ed th e sh or th an d “ fed eral dr ug

sc he du le s.” Se e McFa dd en , 13 5 S . Ct. at 23 06

.

W e al so di sa gr ee th at th e di st ric t co ur t ne ed ed to fin d th at Sh arp kn ew th at

th ere was a hi gh pr ob ab il it y th at th e su bs ta nc e was s p e c i f i cal ly on th e co nt ro ll ed

su bs ta nc e sc he du le s. Evi de nc e in th e reco rd th at Sh arp be li ev ed th at th ere was a hi gh

pr ob ab il it y th at th e su bs ta nc e was an an al og ue is su ffi ci en t f o r e st ab li sh in g wil lfu l

b l i n dn es s. Und er fed eral la w, an al og ue s are th em se lv es tre at ed as co nt ro l l e d

su bs ta nc es

. Se e 21 U.S.C. § 81 3 (“ A co nt ro ll ed su b s t a n c e an al og ue sh al l, to th e

ex te nt in te nd ed fo r hu m an co ns um pt io n, be treat ed

, fo r th e p ur po se s of any Fed eral

la w as a co nt ro ll ed su bs ta nc e in sc he du le I.”). Mo reo ve r, th e Gov ern m en t n eed s t o

es ta bl is h on ly ge ne ral cri m in al in te nt to ob ta in a co nv ic ti on un de r Sect io n 84 1( a). As

we ha ve ex p l a in ed

, “ The Gov ern m en t is no t req ui red to pr ov e th at th e de fen da nt

act ua ll y kn ew th e ex act na t u r e o f t h e su bs ta nc e wit h whi ch he was de al in g. The

-1 2-‘kno win gl y ’ el em en t of th e of fen se refe rs to a ge ne ral cri m in al in te nt

, i.e., aware ne ss

th at th e su bs ta nc e po ss es se d was a co nt ro ll ed su bs ta nc e of so m e ki nd .” Uni te d St at es

v. Ramo s

, 81 4 F.3 d 91 0, 91 5 (8 th Ci r. 20 16 ) (in te rn al qu ot at io n m ark s an d al te rat io ns

om it te d)

, cer t. de ni ed

, 13 7 S. Ct

. 17 7 (2 01 6)

. In ot he r wor ds

, whe n th e Gov ern m en t

pr ov es be y on d a reas on ab le do ub t th at a de fen da nt be li ev ed th at a su bs ta nc e was an

an al og ue in te nd ed fo r hu m an co ns um pt io n, th at de fen da nt can no t es cap e li ab il it y

be cau se th e su bs ta nc e tu rn ed ou t to ha ve be en on th e co nt ro ll ed su bs ta nc e sc he du le s.

The be li ef th at he po ss es se d an an al og ue es ta bl is he s th e de fen da nt ’s kn owl ed ge

.

The refo re, th e m ag is tra te jud ge ’s ge ne ral iz ed refe ren ce to th e CSA an d th e Ana lo gu e

Act was su ffi ci en t t o e st ab li sh a fact ua l b as is for th e p le a. 4

Seco nd

, aft er es ta bl is hi ng th at Sh arp th ou gh t th at th ere was a hi gh pr ob ab il it y

th at th e su bs ta nc es in hi s po ss es si on were co nt ro ll ed su bs ta nc es

, th e m ag is tra te jud ge

as ke d if Sh arp to ok “ de li be rat e act io n to av oi d le arn in g th e t r u e id en ti ty of th e

su bs ta nc e an d whe t he r or no t, in fact

, it was su bjec t of a fed eral dr ug la w? ” Sh arp

an swe red

, “ By no t ge tt in g it t e s t e d

, yes, y es

, I di d.” Sh arp no w arg ue s th at th is

an swe r is in su ffi ci en t to su pp or t wil lfu l bl in dn es s be cau se he ad m it te d o nl y th at he

ha d no t ha d th e pr od uc t te s t e d

, m is ta ke nl y be li ev in g th at th is in it se lf es ta bl is he d

wil lfu l b li nd ne ss . He no w m ai nt ai ns th at th is ass um pt io n was wron g b ecau se th ere

is no t an affi rm at iv e o bl ig at io n t o h av e a p ro du ct tes te d.

As m en ti on ed ab ov e, a fact ua l ba si s r e q u i r e s on ly th at “ th e reco rd co nt ai ns

s u ffi ci en t ev id en ce at th e ti m e of th e pl ea up on whi ch a co ur t m ay reas on ab l y

de te rm in e th at th e de fen da nt li ke ly co m m it te d th e of

fen se .” Ch en ey

, 57 1 F.3 d at 76 9

The Gov ern m en t’s Ru le 11 le t t e r al so co nt ai ns ad di ti on al in fo rm at io n 4

su gg es ti ng Sh arp ha d th e req ui si te kn owl ed ge

. It de sc rib es ho w S h arp ’s e m pl oyee

to ld th e co nf

id en ti al so ur ce who vi si te d S h a r p ’s st or e th at Sh arp was no t in an d

“ pr ob ab ly to ok it w i t h h i m.” The em pl oyee ad de d th at

, wit h “ rai ds ha pp en in g

ev eryw he re,” Sh arp was “ jus t b ei ng sm art .”

-1 3-( in te rn al qu ot at io n m ark s om it te d)

. The m ag is tra te jud ge ex pl ic it ly as ke d whe th e r

Sh arp t o o k de li be rat e act io n to av oi d le arn in g th e tru e id en ti ty of th e su bs ta nc e.

Sh arp an swe red y es an d pr ov id ed an ex am pl e of a rel ev an t om is si on

. As a res ul t, th e

di st ric t co ur t’s co nc lu si on th at th ere is a su ffi ci en t fact ua l ba si s is reas on ab le

. Se e

Flo re z , 36 8 F .3d at 1 04 4.

Fo r th es e reas on s, Sh arp ’s gu il ty pl ea res ts on an ad eq ua te fact ua l ba si s an d th e

di st ric t co ur t d id no t ab us e it s d is cret io n i n d en y in g h is m ot io n.

C. Court ’s fai lu re to reco ns id er th e m ot io n su a s po nt e

Fi na ll y

, S ha rp arg ue s th at th e di st ric t co ur t sh ou ld ha ve reco ns id ered hi s

m ot i o n t o wit hd raw th e gu il ty pl ea su a sp on te at se nt en ci ng

. Bec au se he fai le d to

ren ew hi s m ot io n to wit hd raw hi s gu il ty pl ea at se nt en ci ng

, we rev ie w fo r pl ai n erro r.

Se e Uni te d St at es v. Pat e

, 51 8 F

. 3 d 97 2, 97 5 (8 th Ci r. 20 08 ). Und er pl ai n erro r

rev ie w, Sh arp m

us t pr ov e th at (1 ) th ere was erro r, (2 ) th at was pl ai n, an d (3 ) affe ct ed

su bs ta nt ia l rig ht s. Se e Uni te d St at es v. Ade ju mo

, 77 2 F.3 d 51 3, 53 8 (8 th Ci r. 20 14 ).

If th es e t h r e e c o nd it io ns are m et

, we m ay ex erci se ou r “ di sc ret io n to co rrec t th e

fo rfei te d erro r if th e erro r se rio us ly affe ct s th e fai rn es s, in te gr it y or pu bl ic rep ut at io n

of jud ic ia l pr oc eed in gs .” Mol in a- Mar ti ne z v. Uni te d S t a t e s

, 1 3 6 S. Ct . 1 33 8, 13 43

(2 01 6) (in te rn al qu ot at io n m ark s o m it te d)

.

Sh arp m ai nt ai ns th at th e te le ph on e r e c o r d in gs of hi s co nv ers at io ns wit h

Sch wart z an d th e te st im on y of se ve ral wit ne ss es co rro bo rat e hi s cl ai m s of in no cen ce

an d sh o w t h at th e di st ric t co ur t was wro ng to cred it Sch wart z’s te st im on y ov er hi s

own

. As a res ul t, he su gg es ts th at th e di st ric t co ur t sh ou ld ha ve reco ns id ered hi s

mo t i o n to wit hd raw hi s gu il ty p le a ev en th ou gh he di d no t ren ew it

. Tho ug h m uc h

of t h i s ev id en ce ech oe s Sh arp ’s in si st en ce th at he be li ev ed th e su bs ta nc e was

THJ-0 11

, it ne ve rth el es s f a il s to reh ab il it at e hi s cred ib il it y

. Abo ve al l, Had i

-1 4-Sh arai ri’s te st im on y —s ug ge st in g th at Sh arp ur ge d hi m to l i e t o th e

po li ce— un de rm in es Sh arp ’s pro te st at io ns of i nn oc en ce.

Be c au se th e ev id en ce el ic it ed at se nt en ci ng ne it he r reh ab il it at es Sh arp ’s

cred ib il it y no r un de rm in es th e ev id en ce of hi s gu il t, th e di st ric t co ur t di d no t pl ai nl y

err i n fa il in g t o re co ns id er t he m ot io n t o wi th dr aw th e g ui lt y pl ea su a s

po nt e

.

II I.

Acco rd in gl y

, we affi rm Sh arp ’s co nv ic ti on b e c au se th e di st ric t co ur t di d no t

ab us e it s di sc ret io n in de nyin g Sh arp ’s m ot io n to wit hd raw hi s gu il ty pl ea or pl ai nl y

err i n re fu si ng to reco ns id er t ha t m ot io n su a s po nt e at s en te nc in g.

__ __ __ __ __ __ __ __ __ __ __ __ __ __ __

-1 5-