Th e Ho no ra ble Son ia Sot oma y or , o ri g ina lly

a me mbe r o f t

he pa ne l th a t de c ide d th is * case , was e levated to the Supre me Court on August 8, 2009. The two re maining me mbers of the pa ne l, who are in a g re e me nt, have de te rm ine d th e matte r. Se e 28 U. S.C. § 4 6( d) ; L oc a l Ru le 0.14(2); United States v. De simone, 140 F.3d 457 (2d Cir. 1998)
. 1 05 -69 49 -cr United States v . Maham ed U N IT E D S T A T E S C O U R T O F A P P E A LS F O R T H E S E C O N D C IR C U IT

_______________________________ August Term, 2006 (Argued: May

4, 2007 Dec ided: September 19, 2008) (Petitions for Rehea

ringDec ided: August 21, 2009) Docke t No. 05-6949-c r Amended O pinion

_______________________________ UNI TED STATES OF AMERI CA,

Appellee , v. AB DI RASHI D MOHAMED HASSAN, De fe nd ant- Ap pe lla nt.

____________________________________ B e fo re : CA L AB RES Iand POO L ER, Cir c uit

Judg e s. *

____________________________________ Def endant- Appellant Abdira shid Mohamed Hassa n appea ls from the Nove mber 28, 2005 judgme nt of the United States District Court for the Easter n District of Ne w York ( Gar aufis, J.),
c onvic tin g him , f

oll ow inga

jur y tr ia l, o f o ne c ount o f c on sp ir a c y to i mpo rt c a thi no ne , in2

vio latio n o f 2 1 U .S. C. § § 9 52 (a ), 96 3, on e c ount o f c on sp ir a c y to d istri bute and

to p os se ss w ith int e nt t o d istri bute c athi no ne in v iol atio n o f 2 1 U .S. C. § § 8 41 (a ), 84 6, on e c ount o f c on sp ir a c y to launder money in violation of 18 U.S.C. § 1956(a)(1), ( h), and f orty -one substantive c ounts of money launder ing, in violation of 18 U.S.C. § 1956(a) (1). B eca use we conclude that the evidenc e wa s insufficient to convict Ha ssan of the f orty -one substantive c ounts of money la un de ri ng , in

vio latio n o f 1 8 U .S. C. § 19 56 (a )( 1) , w e REV ERS E the jud g me nt o n th e se c ounts , and dire ct the district cour t to enter a

n order of ac quittal. Bec ause w e conc lude that the district court made a funda

mental er ror in its jury

instructions, we now VA CATE the judg ment as to the
rema ining c ounts. This opini on repla ces in its entirety our ea rlier de cision in United States v. Hassan, 542 F .3d 968 (2d Cir. 2008) (“ Hassan I ”).

I RA M. FEI

NB ERG, Hog an & Har

tson, L .L .P., New Yor

k, NY, for De fe nd ant- Ap pe lla

nt. MA RY K. B ARR, A ssi sta nt Unit e d St a te s A tto rn e y (R os ly nn R. Mauskopf, United States Attorne y for the E astern D istrict of NewYork, Ba rbar a D. Unde rwood, Counsel to the United States Attorne y , on the brief) , Br ookly

n, NY, for

Appellee
.

_________________________________ POOL ER, Circuit J udg e: Def endant- Appellant Abdira shid Mohamed Hassa n appea ls from the Nove mber 28, 2005 judgme nt of the United States District Court for the Easter n District of Ne w York ( Gar aufis, J.),
c onvic tin g him , f

oll ow inga

jur y tr ia l, o f o ne c ount o f c on sp ir a c y to i mpo rt c a thi no ne , in vio latio n o f 2 1 U .S. C. § § 9 52 (a ), 96 3, on e c ount o f c on sp ir a c y to d istri bute and

to p os se ss w ith int e nt t o d istri bute c athi no ne in v iol atio n o f 2 1 U .S. C. § § 8 41 (a ), 84 6, on e c ount o f c on sp ir a c y toAs noted, this amended opinion re place s in its entirety our ea rlier de cision in United 1 States v. Hassan, 542 F .3d 968 (2d Cir. 2008) (“ Hassan I ”), to whic h both parties petitioned for re he ari ng . H avin g re vie we d th e pe tit ion s, we have c on c lud e d th a t e a c h p re se nts a t le a st o ne va lid g round for

g rantingrehe aringand have amende d the opinion acc ording ly . We gr ant Hassa n’s reque st that we consider

the suffic iency

of the e vidence for the sing le count of mone y launder ing c on sp ir a c y

be c a us e we a g re e that w e are re qu ir e d to re a c h th a t is su e sin c e Ha ssa n’ s r e tr ia l w ou ld be bar red by Double Jeopardy

if the evide nce pr esente d by the g overnme nt was insufficie nt. See United States v. Rigg i, 541 F.3d 94, 108 (2d Cir. 2008). We c onclude that the tr ial evidenc e wa s sufficie nt to support a conviction on this count. We decline Ha ssan’s invitation to revisit our conclusion that the trial e vidence was suff icient to prove that he was de aling with khat containing cathinone. We grant the g overnme nt’s reque st that we ame nd the opinion’s descr iption of the e le me nts of

a Contr oll e d Su

bs tanc e s A c t ( “ CSA ” ) c on sp ir a c y and have de le te d th a t la

ngua g e in Hassan I indicating that there is an overt a ct re quirement for conspirac ies cha

rg ed under

the Co n tr o ll e d

Su b s ta n c e s A c t ( “ CS A ” )
. Se e U n it e d St a te s v . Sh a

b an i, 5 1 3 U
. S. 1 0 , 1 5 ( 1 9 9 4 )
. We a lso g ra nt t he g ov e rnme nt’ s r e qu e st that w e ame nd the op ini on

to c lari fy tha t “ sc ie nte r w ith respe ct to the ty

pe and qua

ntity of controlled substanc e is not require d to convict a de fenda nt under the CSA,” Gov’t Pet. for Reh’ g at 5-6, but make only limit ed ame ndments as we think our 3 launder money in violation of 18 U.S.C. § 1956(a)(1), ( h), and f orty -one substantive c ounts of money launder ing, in violation of 18 U.S.C. § 1956(a) (1). On a ppeal, Ha ssan ar g ues that: (1) the district court e rre d in its i nstructions to the jury ; (2) the statute a nd regulations gove rning cathinone do not pr ovide fa ir war ning a s to what conduc t is unlawful; (3) the e vidence was insufficient to support his convictions; (4) the g overnme nt’s failure to corre ct fa lse and misleading testimony

denied him a f

air trial; (5) trial counsel pr ovided ineff ective a ssistance; (6) the district court e rre d in admitting a c hemist’s testimony and exhibits reg ardingthe testing of three samples of khat; and (7) the district c ourt’s sentenc ing de termination was e rrone ous and
unrea sonable. B eca

use we conclude that the evidenc e wa s insufficient to convict Ha ssan of the forty -one substantive c ounts of money launder ing, in violation of 18 U.S.C. § 1956(a) (1), we REVERSE the judgment on these counts, and dire ct the district cour t to enter a

n order of acquittal. B eca

use we conclude that the district court made a funda mental er ror in its jury ins tr uc tio ns , w e no w V AC AT E the jud g me nt a s to the re ma ini ngc ounts . 1decision re ad as a whole make s clea

r that we adher e to that rule. H oweve r, we deny the g overnme nt’s reque st that we re visit our conclusion that a “c onviction based on c athine, rather than cathinone, would have be en an imper missibl e construc tive amendment of the indictment.” Hassan I , 542 F.3d at 991. We adhere to that conclusion. See United States v. Abdulle, 564 F .3d 11 9, 12 6- 27 (2 d Ci r. 20 09 ) ( e xpla ini ngwhy c onvic tio n b a se d o n c a thi ne , r a the r t ha n c a thi no ne , is constructive a

mendment rather than va

rianc e). We de ny

the g overnme nt’s and Ha ssan’s petitions in all ot her r espec ts. 4 I. BACKG ROUND A. Khat Hassan w as convic ted of c ontrolled substance and money launder ing of

fense s involving cathinone, a

stimul ant that is sometimes present in “khat.” Khat is the lea f of the pla nt catha edulis, a shrub that g rows in par ts of East Afr ica a

nd the Ara

bian Peninsula. See United States F oo d a nd Dr ugAd min istratio n, B a sis fo r t

he Re c omm e nd a tio n f

or Contr ol o f C a thi no ne int o Schedule I

of the Controlled Substance A ct 9 (Nov. 5, 1992) [hereinaf ter “ FDAReport”]; United States v. Hassan, 03- cr- 567, slip op. at 1 (E.D.N.Y. O ct. 12, 2005). “ The plant’s le aves a re chew ed or br ewe d in tea and, onc e ing ested, produc e a stimulant eff ect on the c entra l nervous sy stem.” I d. Whil e “khat is . . . ingested a s regularly in East Afric an countr ies (such a s Somalia, where the def endant is fr om) as cof

fee is inge sted in the United States,” id. at 8, the two stimulants that
can some times be found within khat, cathinone and cathine, have none theless bee n deeme d “contr olled substances” under United States law, see 21 C.F.R. §§ 1308.11(f) , 1308.14(e) ; see also 21 U.S.C. § 812. Cathinone, which has prope rties similar to those of amphetamines, is the strong er of

the two substance s. I t is “very unstable” a

nd “ra pidly decompose s into less potent substances,” including c athine. See F DA Report at 9. Accor ding to the D rugEnforc ement Administration, “[w] ithin 48 hours of harve st Khat’s che mical composition breaks down and at5

that point Khat contains only Cathine, the sche dule I V substance .” U.S. DrugEnforc ement Administration, Fac t Sheet, Khat, AKA : Catha Edulis, http:// www.de a.g ov/pubs/pressrel/pr072606a .html (last visi ted August 10, 2008); see a lso FDA Report at 11-12 ( “Khat leaves ha ve bee n repor

ted to lose their ef

fec t within . . . three day s after harve sting.” ); Hassa

n, 03-cr -567, slip op. at 1 (“When the le aves a re f irst cut, they

contain a stimul ant ca lled cathinone. O ver a period of a

pproxi mately

48-72 hours, the c athinone in the plant deg rade s into cathine, a milder stimulant.”). Mor eover , acc ordingto a re cent a rticle in the J ournal of D rugI ssues, “[a]ny claim that khat alwa

y s contains cathine is unsubstantiated.” Edwar d G. Armstrong , Resear ch Note: Crime, Chemica ls, and Culture: On the Complex ity of Khat, 2008 J. Drug I ssues 639. Additionally , as the F ourth Circuit has noted: “At this juncture, there is no reasona

ble basis for the conclusion that khat a lway s contains cathine.” Ar g aw v. Ashcrof t, 395 F.3d 521, 526 (4th Cir. 2005). Kh at it se lf

is n ot a c on tr oll e d s ub sta

nc e un de r Unit e d St a te s la w. Ho we ve r, kh a t is subject to an unusual a

nd, indeed, unique dua l regulatory scheme that employ s a distinction ba se d u po n th e c he mic a l c omp os iti on of kh a t. “ Whe n k

hat c on ta ins c a thi no ne , k

hat is a Schedule I

substance,” and “[w]hen khat does not conta in cathinone, but does c ontain cathine, khat is a Schedule I V substance .” Schedule s of Controlled Substances: Placeme nt of Cathinone and 2,5-D imethox y -4-e thy lamphetamine Into Schedule I , 58 Fe d. Reg . 4316, 4317 (Jan. 14, 19 93 ); se e a lso Un ite d St ate s v . Ca se e r, 39 9 F .3 d 8 28 , 8 33 (6 th C ir . 2 00 5) (“ [N]e ith e r t he U. S. Code nor the Code of

Fe dera l Reg ulations controlled substance s schedules r efe rs to the plant from which c athinone is derive d, Catha edulis, commonly known as ‘khat.’”); Ar g aw, 395 F .3d
a t 52 7 ( “ [K]hat is no t a

c on tr oll e d s ub sta

nc e . . . . ” ); Un ite d St a te s v . H us se in, 35 1 F .3 d 9 , 1 7 ( 1s tHa ssa n a rgue s th at c athi ne ’s lis tin g a s a c on tr oll e d s ub sta

nc e is n o lo ng e r v a lid

be c a us e 2 a te mpo ra ry lis tin g c ann ot s ub sti tut e ind e fi nit e ly fo r t he re qu ir e d r

ule makin g pr oc e ss. B e c a us e Hassan w as not cha

rg ed with a c athine off

ense, w e do not re ach this issue. 6 Cir. 2003) (“[K]hat, unlike coca ine, is not a controlled substanc e per se . . . .”) . I mportation or dis tr ibutio n o f c athi no ne , th e Sc he du le Isu bs ta nc e , is su bje c t to a ma ximumpe na lty

of tw e nty y e ars , s e e 21 U. S.C. § 9 60 (b )( 3) (i mpo rt a tio n) ; 21 U. S.C. § 8 41 (b )( 1) (C ) ( dis tr ibutio n) , w hil e importation of cathine, which was “ temporar ily ” plac ed on Schedule I V in 1988, see 53 F ed. 2 Reg . 17,459 (May

17, 1988), is subject to a maximum penalty of five year s, see 21 U.S.C. § 96 0( b) (4 ); se e a lso 21 U. S.C. § 8 41 (b )( 2) (m a ximumpe na lty fo r p os se ssi ngc a thi ne wi th i nte nt t o distribute is three y ear s’ imprisonment).

B. Hassan’s T rial 1. The Evidence The e vidence at trial demonstrated that Hassa n had bee n importing khat into the United States for seve ral y ear s with the assistance of a United States Customs broker named Patrick Fuller . Fuller

provided Ha ssan with counter feit customs stamps, which helpe d rele ase g oods from United States Customs quickly and without inspection. Hassa n’s khat shipments wer e falsely labeled a s printed matter, or simil ar material, a

nd used fake re turn addre sses. Hassa n, who was f

irst introduced to F uller in 1997 or 1998, wa s one of F uller’s princ ipal clients. Fuller estimated that he he lped Hassa n import two to three shipments of khat pe r we ek, and H assan paid Fuller

$1,500 for e ach suc cessf ul shipment. Hassan also took Fuller to L ondon and introduced him to a man na med Omar

Hashi who told Fuller

that he wa s Hassan’ s khat supplier. Fuller worke d with severa l other khat importer s, including a man named Moha

medKa sta va thu s mi sst ate d th e law r e g ard ingkh a t to Ha ssa n. Kh a t it se lf

is n ot i lle g a l, 3 rathe r, only

khat containingcathinone or cathine is illeg al. See supra Part I (A). 7 Hassan - - no re lation to defenda nt -- who c ooperated with the g overnme nt [ here inafter “the
c oo pe rator ” ]. T he c oo pe rator te sti fi e d th a t, l ike a

numbe r o f o the r k

hat im po rt e rs , h e re g ula

rl y took way bills t o Fuller

to be stamped with the c ounterfe it customs st amps. In 2002, another khat importer, Ahmed Mussa , introduced the cooper ator to a ma n named L eban. T he coope rator me t with L eban se vera l times, but, ul timately , the two did not succe ssfully neg otiate a de al. The
c oo pe rator

late r i de nti fi e d d e fe nd ant H a ssa n a s L e ba n in a ph oto arr ay ; ho we ve r, wh e n a sk e d to identify L eban in the c ourtroom duringtrial, the coope rator f ailed to identify

defe ndant Hassa

n as L eban. Prior to his arre st in 2003, Hassan had two khat-related enc ounters with law e nforc ement authorities. On Apr il 4, 2001, Hassan wa s briefly detained at J ohn F. Ke nnedy Airport (“ J FK” ) when he and anothe r individual tried to pick up two shipments of khat fr om a ca rg o fac ility . At the time, Hassan told United States Customs Special Ag ent Paul Kastava that he thoug ht that khat was le g al in the United States, bec ause it wa s leg al in Gre at B ritain. In response , Special Ag e nt K a sta

va inf or me d H a ssa

n th at kh a t is ill e g a l in

the Un ite d St a te s. Ho we ve r, Ka sta va did 3 not inform Hassan that khat is ill eg al bec ause it is, or ca n be, a c ontrolled substance . Rather, he simply told Hassan that khat is illeg al. Although the shipment of khat was se ized, Hassan wa s not arre sted. The g overnme nt argues, and the district court found, that testimony about this encounter

supports the argument that Hassan kne w “that khat contains a c ontrolled substance .” Ha ssan, 03-c r-567, slip. op. at 12. Hassan, on the other ha

nd, argues that this encounter actua lly supports his assertion that he wa s8

not awar e that khat is, or c an be, a controlled substanc e in the United States. Spec ial Ag ent Ka s t av a d i d

n o ts t at e t h atkh atwa s a c o n tro l l eds u b s t an ce , an d

Ha s s an wa s n o tarre s t ed , al th o u gh
o n e w o u l d

e x p e c tt o b e , i f

c a u g h ti mp o rt i n g c o n tr o l l e d s u b s t an c e s i n t o th e U n i t e d

S t a t e s b y a United States Customs Agent. Thus, Ha ssan ar g ues that his encounte r at JFK with Special Ag ent Ka sta va me re ly pr ov e s th at he wa s awa

re that im po rt ingkh a t vi olate s U .S. Cus tom s la ws . Hassan’ s second e ncounter with law enf

orce ment reg ardingkhat was on Ma y 9, 2002, at
a bo nd he ari ngfo r f

e llo w k hat im po rt e r Ahme d M us sa . H avin g be e n c a ug ht i mpo rt ingkh a t in to the United States, Mussa wa s not charg ed with violating United States druglaws, but rathe r wa s
c ha rg e d w ithimp or

tin g me rc ha

nd ise int o th e Un ite d St a te s, by me ans of a fa lse state me nt t o Customs , in violation of 18 U.S.C. § 542. Hassan, who desc ribed himself a s a fr iend of Mussa’ s family who did not know Mussa himself, testified brief ly at the hea

ringand co- signe d a bond on Mussa’s beha lf. The bond did not identify the cha rg es ag ainst Mussa. Duringthe hea ring , the prosec utor and Mussa’ s attorney both made re fer ence to the fac t that “the under lying c onduct here was importation of drug s” and “ the under lying of fense involves drug s.” Hassan w as ar

rested on A

pril 16, 2003. I nvestig ating ag ents from the B urea u of I mmigration and Customs Enforc ement tra ced a United Parc el Service (“U PS”) delivery of khat to an offic e building at 19 West 22nd S tree t in New Yor k City (the “ office building”)
. I mmediately

afte r the pa ckag e wa s delivere d by the UPS driver, and sig ned for by co-de fenda

nt Mahame d Mahame d (the “ co-de fenda nt”), Spec ial Ag ent Stephen L ee w ent to the offic e building and aske d the co- defe ndant to take him to the UPS packag e. The co-de fenda nt showed Specia l Ag ent L ee the packa g e, which ha d been pla ced on the floor of a closet adja cent to the of

fice building’s lobby . In response to questioning, the c o-def endant told the investig ating ag ents thatAs state d p re vio us ly , it wa s a c tua lly

a t JFK , n ot N e wa

rk , th a t H a ssa

n h a d r un int o 4 previous trouble w ith U.S. C ustoms. 9 Hassan w as re sponsible for ar rang ing shipments of khat to the office building, that the c odefe ndant would sig n for the pa ckag es, and that the two men would split the contents. Hassan
arr ived shortly

there afte r and w as ar

rested. H assan initially

told the ag ents that he wa s at the office building to pick up a ke y to the co-de fenda

nt’s residenc e, whe re a

sick relative was sta ying . A ft e r f

ur the r q ue sti on ing , H a ssa

n a c kn ow le dg e d th a t he ha d p re vio us ly ru n into t ro ub le wi th U .S. Cus tom s w he n h e tr ie d to pic k u p k hat at N e wa

rk Ai rp or t. 4 After he wa s arr ested, Ha ssan allowed a g ents to sear ch his bac kpack a nd apar tment. Among other thing s, the bac kpack c ontained $12,642 in ca sh, a UPS airway bill addressed to the office building, and r ece ipts for postal money order s. The bac kpack a lso contained notebooks and date books which appe are d to be re cords of khat transa ctions, listi ng names of c ouriers a nd kn ow n c o- c on sp ir ator s, c ity name s, and

c a lc ulatio ns . In H a ssa

n’ s a pa rtme nt, inv e sti g a tin g a g e nts fo un d mo re mon e y

or de r r e c e ipt s and

UPS a ir wa y bil ls a dd re sse d to the of

fi c e bu ild ing , a s w e ll as a lug g ag e tagbear ing the name a nd addre ss of an individual who had be en ar rested thr ee months earlier

at J FK f or smug g ling khat in his l ug g ag e. Af ter Ha ssan’s ar

rest, investig ating ag ents obtained a dditional recor ds of money order s purcha sed by

Hassan be tween D ece mber 21, 19 98 , a nd May 15 , 2 00 0, pa

y a ble to h is k

hat su pp lie r i n L on do n, Om ar H a sh i. At trial, the g overnme nt offer ed evide nce attempting to conne ct Hassa n to other importations of khat. A customs offic er te stified that on J une 3, 2000 he ha d seized khat from the bag s of Robert L ightbody , a citizen of the United K ingdom, who w as attemptingto enter the United States at JFK. Customs rec ords showed that an individual of the same na me also ar

rived10

in the United States on Novembe r 8, 1999; L ightbody ’s name a ppear ed in one of

Hassan’ s cale ndars f

or that date , alongwith the notation “L ightbody , 400 plus 120.” The g overnme nt also prese nted the testimony of a D rugEnforc ement Administration (“D EA”) chemist, Br ian Hall. Ha ll testified about analy ses he pe rfor med on three packa g es of khat to deter

mine the che mical composition of the khat, i.e., whe ther the khat contained e ither cathinone or

cathine. H all did not analy ze the packa g e of khat that was seized the day that Hassan w as ar

rested, a nd thus provided no testimony as to the che mical composition of that khat shipment. I nstead, Ha ll testified about three packa g es of khat that the DEA ha d seized after Ha ssa n w a s arr e ste d. No ne of

the pa c ka g e s w e re a dd

re sse d to Ha ssa

n. Ho we ve r, the fi rs t pa c ka g e wa s a

pp are ntl y se ize d at th e of

fi c e bu ild ing . T he oth e r t wo pa c ka g e s w e re se ize d at a UPS facility . Hall testified that ea ch of the samples that he teste d from these three packa g es contained both c athinone and c athine. He also testified that cathinone, which ca nnot be detec ted without chemical testing , beg ins to lose its potency within 48 to 72 hours, when it starts to break down into cathine. 2. Proc e dural H

ist or y The c ase w as tried be fore a jury from Jul y

11, 2005, to J uly

14, 2005. On the first da y of trial, Hassa

n filed a motion in limi ne see king to pr event the pr osecution or its witnesses fr om stating, inter

alia, that khat is a c ontrolled substance . The g overnme nt conce ded that “khat in and of itself, without any

cathinone[,] is not nece ssarily a contr olled substance,” but pointed out that khat “may

contain” c athinone. The district court ruled that the g overnme nt “would not be permitted to introduce e vidence that khat per se is a contr olled substance.” Hassan, 03- cr- 567, slip. op. at 15. Nothwithstanding this restriction, a numbe r of individuals testified throug hout the11

trial that khat is, in fac t, a controlled substanc e. Amongthese we re se vera l law enf orce ment personne l. Special Ag ent Kastava testified that to his “unde rstanding ” khat is “a n illega l substance in the United States.” Specia l Ag ent L ee te stified that Hassan w as ar rested f or “[c]onspi rac y

to import khat,” answe red a ffirmatively that khat is a “na

rcotic” and “is on the
c on tr oll e d s ub sta

nc e lis t,” and

state d th a t “ I ’m

fa mil iar w ithkh a t . . . a

nd I ’m fa mil iar t hat it is illega l to bring khat into the United States.” Special Ag ent David Villanuc ci, a Spec ial Ag ent with the I mmigration Cust oms Enforce ment, testified that he a rre sted Hassa

n for “ [i ]m portation of kh a t” and

ano the r i nd ivi du a l f

or “ atte mpt ingto i mpo rt

kh at.” Ra lph

Ca fa sso , a

n o ff ic e r w ith the United States customs and borde r protec tion service, te stified that khat is “an illeg al substance.” In addition to the testimony of seve ral lawenfor ceme nt office rs to the ef fec t that khat its e lf is i lle g a l be c a

us e it i s a c on tr oll e d s ub sta

nc e , th e c us tom s b ro ke r P a tr ic k F ull e r a lso testified to the ef

fec t that khat itself is ill eg al in the United States bec ause it is a contr olled substance. H e testified that he pleade d g uilty to “[c]ons pirac y

to import khat,” that khat is “a
c on tr oll e d s ub sta

nc e , s o th at f

a lls un de r d

ru g s, ” and

tha t “ my c ha rg e s is [sic ] co ns pir a c y

to import khat.” Additionally , the coope rator indicated that he plea ded guilty to “importing forbidden stuff

to the United States.” When aske d to clarify what he me ant by

“for bidden stuff,” the coope rator r esponded, “ [t ]he khat.” Whil e Ha ssa

n’ s tr ia l c ouns e l di d n ot e xplic itl y ob je c t to thi s te sti mony , h e did tr y to highlig ht the inacc urate nature of this testimony throug h his cross-e x amination. After hear ing Special Ag ent L ee ina ccur ately testify that khat is illega l in the United States beca use it is on the
c on tr oll e d s ub sta

nc e lis t, H a ssa

n’ s atto rn e y

so ug ht t o c on tr a dic t Sp e c ia l A g e nt L e e ’s te sti mony to12

this effe ct by

prese nting the a ctual wor ding of the Controlled Substances Ac t to the witness. Howeve r, af

ter the pr osecutor obje cted to this line of questioning , stating that it “is bey ond the scope of my direc t,” the district cour

t sustained the g overnme nt’s objection. In response to the district court’s de cision to sustain the objection, Hassan’ s counsel aske d to “re spond for the
rec ord.” H oweve r, the district cour t denied this reque st, stating, “[w]e’ll put it on t he re cord later. L et’s kee p g oing.” L ater in the trial, afte r F uller also testified that khat is a controlled substance, H assan’ s counsel ag ain tried to under mine these stateme nts by

questioning F uller about the che mical composition of khat. Ag ain, the g overnme nt objected to this questioning, a nd the district court sustained the g overnme nt’s objection. At the close of

the g overnme nt’s case , Hassan move d for a judgme nt of ac quittal under Fe dera l Rule of Criminal Procedure 29(a) . The district cour t denied the motion, but defe rre d consideration of Hassan’ s constitutional challeng e to the re g ulatory scheme for post-tria l briefing . Hassan r ested without prese nting a defe nse ca se. At the cha

rg ing c onfer ence , defe nse counse l objected to the f ollowing languag e in the pr op os e d ju

ry c ha rg e fo r C ount O ne : Whil e y ou

mus t f ind that th e de fe nd ant k

ne w i t w a s d

ru g s h e wa s c on sp ir ingto bringinto the United States, y ou need not f ind that the defe ndant knew or believed that it was cathinone, as longas the g overnme nt proves that he kne w and intende d that so me c on tr oll e d s ub sta nc e wo uld

be imp or te d into t he Un ite d St a te s. Def ense c ounsel argued that this char g e wa s far too broad, be cause the g overnme nt’s burden w as to prove that Ha ssan intended to import or distribute cathinone, and not mere ly khat. The c ourt
overr uled these obje ctions, but ag ree d “in the intere st of fairne ss” to chang e the instruction slightly to indicate that the jury

need not f

ind that the defe ndant believe d he wa s importing “a13

drugcalled” cathinone. T he cha rg e as de livered a lso contained the f ollowing languag e, which the g overnme nt char acte rizes as a “ reminder that cathinone w as the c ontrolled substance at issue in the case ”: Whil e you must find that the defe ndant knew it wa s a controlled substanc e he w as conspiringto bring into the United States, y ou need not f ind that the defe ndant knew or believed that it was a drugcalled c athinone, as longas the g overnme nt proves that he knew a

nd intended that some c ontrolled substance would be imported into the United States. As Itold y ou ear lier, cathinone is a controlled substance. Simi lar languag e in the cha rg e for Count Two was not modified af ter trial c ounsel’s initial ob je c tio n. Af

te r b ri e f d e lib e ratio ns , th e jur y fo un d H a ssa

n guil ty on a ll c ounts . Followinghis conviction, Hassan move d ag ain for a judgme nt of ac quittal under Rule 29 and also for

a new trial under Rule 33. F ed. R. Crim. P. 29, 33. On October 12, 2005, the district court denie d these motions in a written opinion. Hassan, 03- cr- 567, slip. op. at 1-18. Relying pr imarily

upon the Fir st Circuit’s decision in United States v. Hussein, 351 F.3d 9, 17 (1st Cir. 2003), the district court r ejec ted Hassa n’s due pr ocess c halleng e to the statutory scheme , be c a us e it f ound that th e statut or

y re qu ir e me nts re g ard ingsp e c if ic int e nt m iti g a te d a

ny va g ue ne ss in the regulatory

scheme for khat. Hassan, 03- cr- 567, slip. op. at 8-9. The district cour t
c on c lud e d th at th e g ov e rnme nt h a d o ff e re d s uf fi c ie nt e vid e nc e to s a tis fy the int e nt e le me nt, namely : (1) Ha ssan “e x pended great effor t to concea l the khat he imported into the United States from law e nforc ement;” id. at 11, ( 2) Ha ssan “made eff orts to import khat into t he United States as quickly

as possible;” id. at 12, and ( 3) Ha ssan “wa s informed on two oc casions that khat contains a c ontrolled substance ,” id. Fina lly , the cour t concluded that the evidenc e wa s
su ff ic ie nt t o s us ta in t

he mon e y la un de ri ngc ha

rg e s, be c a us e Ha ssa n’ s n ote bo ok s “ re c or de d h is14

khat sales,” Hassan’ s Social Security statements and tax returns showe d that the value of the money order s purcha sed excee ded his dec lare d income, and the jury could infer

that Hassan kn e w“ th a tth e s e f

i n an c i a l tr an s a c t i o n s i n v o l v e d p r o c e e d s o f

s o m e f o r mo f un l aw f u l a c t i v i ty” beca use Ha ssan made “ eff

orts to conce al his actions from law enfor ceme nt.” In his Rule 33 moti on, Hassan a rgued that he should be g rante d a new trial bec ause the g overnme nt had re peate dly violated the cour

t’s pre- trial ruling by

ref err ing to khat as a c ontrolled substance a

nd discussing c athine. The district court re jected this ar g ument on sever al g rounds. First, the district cour

t found that the examples cited by Hassan w ere “not direc t violations of the in limi ne orde r.” Sec ond, the district court c oncluded that, e ven if the or der w ere deeme d violated, Hassa

n had not ca

rried his burde n, beca

use it would not be a manife st injust ice to let the verdic t stand in light of the substantial evide nce of his guilt. Third, the district cour t found that Ha ssa n h a d “ e ff

e c tiv e ly wa ive d” any

ob je c tio n p ur su ant t o Ru le 33 , b y fa ili ngto o bje c t at tr ia l to the re levant testimony

and by failingto reque st a limit ing instruc tion on this issue. The district cour

t sentence d Hassan to e ighty -seve n months’ imprisonment and three y ear s of supervise d rele ase on e ach c ount, to run concur rently , and imposed a spe cial asse ssment of $4,400. The c ourt also orde red a $21,100 forf

eiture. This appea l followed. We ag ree d to consider the c ase on a n expedited basis, and, in an order filed on May

9, 2007, afte r ora l argument, we grante d Hassan’ s motion for bail pending appea l. See 18 U.S.C. § 3143(b). We now re verse the judg ment of the district cour t as to the fo rt y -o ne su bs tanti ve c ounts of

mon e y la un de ri ngin v iol a tio n o f 1 8 U .S. C. § 19 56 (a )( 1) be c a us e we f ind that the evidenc e wa s insufficient to sustain those convictions, and va cate the judg ment of the district cour

t on the rema ining c ounts, beca use we find that the district court made a15

fu nd ame nta l and

pr e jud ic ia l e rr or

in i ts j ur y ins tr uc tio ns .

II. DI SCU SSIO N Al mos t a ll o f t

he iss ue s r a ise d b y

Ha ssa n in thi s a pp e a l are int e rt

wi ne d in that th e y a ll imp lic a te sc ie nte r. Thus , w hil e su ff ic ie nc y of the e vid e nc e is a

thr e sh old iss ue tha t ma y ob viate other c halleng es, see United States v. Allen, 127 F .3d 260, 264 (2d Cir. 1997), we beg in here by addre ssing Ha ssan’s due pr ocess c halleng e, bec ause w e believe it helps frame the key issues raised in Ha ssan’s appe al. Cf. Casee r, 399 F .3d at 832-33 (a ddressingvagueness f irst); Hussein, 351 F.3d at 13 (same)
.

A. Due P roce ss Challenge 1. Stan dard of Revie w We reviewde novo cha lleng es to the constitutionality of a statute. United States v. Giordano, 442 F .3d 30, 38-39 (2d Cir. 2006). 2. The Contr olled Subs tance Act is Not Unconsti tuti onally V ague as Applied to Has san Ha ssa n c on te nd s th at th e Contr oll e d Su bs tanc e Ac t ( “ CSA ” ) i s unc on sti tut ion a l a s it
a pp lie s to kh at, 2 1 U .S. C. § 84 1, be c a us e it v iol a te s th e Du e Pr oc e ss C la us e of the F if th Am e ndme nt b y

fa ili ngto p ro vid e the de fe nd ant w ithfa ir wa rn ingtha t hi s c on du c t is un lawf

ul. Specifica lly , Hassan a

rgues that a pe rson of ordina ry intelligenc e would not be a ble to deter

mine
-- e ven upon close inspection of the r eleva nt statute and re g ulations -- that the importation or distribution of khat is unlawful, that khat may contain a c ontrolled substance , the nature of that
c on tr oll e d s ub sta

nc e , o r t he se ri ou sn e ss o f a

kh at- re late d o ff

e ns e . H a ssa

n r oo ts h is a

rgume nt i n16

the fa ct that the CSA does not expli citly mention the word “ khat” while othe r botanica l sources
are listed in the CS A; that the che micals that are mentioned in the CSA relatingto khat --
c a thi no ne and

c athi ne -- are ob sc ur e and unkn ow n to the ave ra g e pe rs on ; and that be c a us e cathinone r apidly

deter iorates into cathine, it is i mpossible to know without chemical testing whether these c hemicals a

re pr esent in any

particula r supply of khat. F urthermor e, Ha ssan notes that the obscurity

of the CSA as it relate s to khat is especia lly troublesome g iven that khat is leg al and socia lly

acc epted in a la

rg e portion of the w orld, including Hassan’ s native Somalia, and that its effe cts are that of a r elatively mild st imulant sim ilar to ca ffe ine. Hassan’ s argument is an issue of first impression in our Circuit. The F irst, Six th, and Eig hth Circuits, however, ha ve all re jected due proce ss challeng es to the khat-r elated r egulatory scheme in the CSA. S ee Ca seer , 399 F.3d at 835-39; United States v. Sheikh, 367 F.3d 756, 763- 64 (8th Cir. 2004) (re lying e ntirely on the Fir st Circuit’s reasoningin Hussein); Hussein, 351 F.3d at 14-16. Her e, the district cour t, while noting the tr oubles associated with the vagueness of the CSA as it relates to khat, f ound that the statute wa s constitutional because the “sc ienter require ment mitigates a

ny vagueness in the law .” B eca use we find persua sive the re asoningof the district court be low, and of the Six th Circuit, we af firm the district cour

t’s deter mination that the statute is not unconstituti onal under the vagueness doc trine. The va g ueness doc trine re quires that, in orde r to be c onstitut ional, a statute must “g ive the per son of ordinar

y intelligenc e a r easona

ble opportunity

to know what is prohibited” a nd

“ pr ov ide e xplic it s tand ard s f or tho se wh o a

pp ly [it].” Gr ay

ne d v . Ci ty

of Roc kf or d, 40 8 U .S. 104, 108 (1972). How ever , the Supreme Court ha s also made c lear that “[w]hen the validity of
an a c t of the Con g re ss i s d

ra wn in q ue sti on , a nd e ve n if a se ri ou s d ou

bt o f c on sti tut ion a lity

is17

raised, it is a c ardina l principle that this Court will first ascerta in whether a construc tion of the statute is fairly

possible by

which the que stion may

be avoide d.” Crowe ll v. Benson, 285 U.S. 22, 62 (1 93 2) ; se e a lso Cha

pma n v . Unit e d St a te s, 50 0 U .S. 45 3, 46 4 ( 19 91 ) ( “ Ev e ry re a so na ble construction must be re sorted to, in order to save a statute from unc onstitut ionality .” (inter nal
c itatio n a nd qu otatio n ma

rk s o mitte d) ). We a

re thu s r e qu ir e d to fi nd

a fe de ra l st a tut e constitutional wheneve r possible. We b e lie ve , a s th e dis tr ic t c ourt fo un d, that w hat sa

ve s th e sta

tut e a t is su e he re -- the CSA as it relate s to khat -- fr om constituti onal trouble is the fa ct that sciente r is require d for a conviction. See Case er, 399 F .3d at 839; see a lso Vill. of Hoffman Estate s v. Flipside, Hoff man Estates, Inc., 455 U.S. 489, 499 (1982) ( “[T] he Court has re cog nized that a scienter require ment may mitigate a

law’s va g ueness, e specia lly with respec t to the adequa cy of notice to the complainant that his conduc t is proscribed.” ); Screw s v. United States, 325 U.S. 91, 102-03 (1945) ( “[W ]here the punishment imposed is only for a n act knowing ly

done with the purpose of doing that which the statute prohibits, the ac cused c annot be sa id to suffer f rom lack of

war ning
or kn ow le dg e that th e a c t w hic h h e do e s is a vio la tio n o f l aw. . . . [A ] re qu ir e me nt o f a sp e c if ic intent . . . saves the Ac t from any char g e of unc onstitut ionality on the g rounds of va g ueness.” ). Crimes arisingout of the importation of controlled substanc es, and c rimes for posse ssion of controlled substanc es with intent to distribut e -- such as Ha ssan was c harg ed with and c onvicted of -- require proof that the de fenda nt committed the offense “knowing ly or intentionally .” 21 U. S.C. §§ 84 1( a )( 1) & 96 0( a )( 1) . A s th e Sixth C ir c uit e xpla ine d in

Ca se e r, “ the c on c e rn

that a person of ordinary intelligenc e could unwitting ly expose himself or herse lf to criminal pena lties due to the vagueness of

the controlled substanc es sche dules with respe ct to khat is overc ome her eWe a re a wa re that, s imi lar t o k

hat, “ ma g ic mus hr oo ms” are no t li ste d in the CSAwh ile 5 the ir ps y c he de lic ingre die nts , p sil oc y bin and ps ilo c y n, are . T hu s, we a g re e wi th t he F ir st C ir c uit that th e re is n o r e lia

ble patte rn

he re . H us se in, 35 1 F .3 d at 16 . N on e the le ss, we a lso a g re e wi th J udg e Holschuh that: (1) “two wr ong s do not make a r ight;” a nd (2) “ when de aling with the constitutional right to be f airly notified that to eng ag e in ce rtain conduc t is a crime, [it is not ] ‘a stretch’ to believe that pe rsons of ordina ry intelligenc e, see ing othe r plants spec ifically listed as beingillega l but not the khat plant, could rea sonably conclude that they

can la wfully possess the khat plant.” Case er, 399 F .3d at 852 (Holschuh, J., concurr ing in pa rt and dissentingin part). 18 beca use . . . convic tion requires a showing of ac tual knowledg e that khat c ontains a controlled substance.” 399 F.3d at 839. I t is thi s require ment of proof of spec ific intent for the conviction at issue -- i.e . that the def endant “ knowing ly

or intentionally ” imported or posse ssed with intent to distribute khat with a controlled substanc e (inde ed, as w e will explain, as charg ed in this case, cathinone spe cifica lly) -- that persua des us that the statute g overningkhat is constitutional as applied to Hassa

n. No ne the le ss, wh ile we be lie ve the statut e is c on sti tut ion a l, w e are sy mpa the tic to Hassan’ s argument beca

use the statutory

scheme , as it relate s to khat, is troubling. He re, r ather than including the words “ khat”or “ca tha edulis” in the a

pplicable r egulations, the regulatory scheme ref

ere nces only

khat’s key

chemica l ingr edients, cathine and cathinone. In contra st to the regulatory

treatment of khat, Cong ress did list four botanica l sources - - ca nnabis, coc a, peyote, and poppy

-- in the CSA in addition to their chemica l ingr edients. We ag ree with Hassan, a nd 5 the district court, that it would be he lpful to people, who a ctually resor t to statutes and regulations to determine whe ther their c onduct is lawful, for Congr ess, throug h the statutory or regulatory

scheme , to include the wor d “khat” in the CSA. However , we do not believe that Congr ess was r equire d to do so. See Hussein, 351 F .3d at 15 (“ Due pr ocess doe s not require the statut e sp e c if

ic a lly to p ro hib it e ith e r ‘ kh a t’ or ‘k hat c on ta ini ngc a thi no ne ’ a s a pr e c on dit ion

toTestimony that occur

red at trial supports this posi tion: The cooper ator (Moha med 6 Hassan) , a witness who ha d made his ca ree r in the khat tra de, testified that he had neve r hea rd of “cathinone;” and the g overnme nt’s DEA c hemist testified that he had ne ver he ard the term cathinone until traine d by the DEA. 19 c onvic tio n. ” ); se e a lso Un ite d St ate s v . Po we ll, 42 3 U .S. 87 , 9 4 ( 19 74 ) ( “ Th e fa c t th a t Co ng re ss might, without difficulty , have c hosen cle are r and more prec ise languag e equa lly capa ble of
a c hie vin g the e nd

wh ic h it so ug ht d oe s n ot m e an th a t th e statut e wh ic h it in f a c t dr a ft e d is unconstitutionally

vague.” ( internal quotation and c itation omit ted)). As the Sixth C ir c uit

e mph a size d in

Ca se e r, wh ile the du e pr oc e ss c ha lle ng e s r a ise d in kh a t c a se s are un iqu e , th e y no ne the le ss i mpl ic a te se ri ou s c on sti tut ion a l c on c e rn s b e c a us e “[w]hen a statute is prec ise on its face y et latently vague, the da

ng er of persons be ing c aug ht
un awa re of the c ri min a lity

of the ir c on du c t is high. ” 39 9 F .3 d at 83 6. Mo re ov e r, wh ile ignor ance of the lawis no ex cuse, that principle “ma y be abr og ated whe n a law is ‘so te chnica l or obscure that it threatens to ensna re individuals eng ag ed in appa rently innocent conduc t.’” I d. at 837 (quoting United States v. Napie r, 233 F .3d 394, 397-98 (6th Cir. 2000)). “ Her e, the ter m ‘cathinone’ is sufficie ntly obscure that persons of or dinary intelligenc e re adingthe controlled substances sc hedules proba bly would not discern that possession of khat containing cathinone and/or c athine constitutes possession of a c ontrolled substance .” I d. at 838. Fur thermore , 6 mainstream dictionar ies provide no he lp, as they do not define c athinone or me ntion it when they d ef i n e kh at . I d
. (c i t i n g A MER I C AN H ER I TA GE D I CTI ONA RY OF THE E NGL I S H L ANGUAG E , M ER R I AM -W EB S TER ’ S C OL L EGI AT E D I CT I O N A RY , and the O XF OR D E NGL I S H D I CT I O N A RY ). Thus, while we a g ree with our sister circ uits that the statute withstands constitut ional scrutiny beca use of the sc ienter r equire ment, i.e., that the g overnme nt was re quired to prove that20

de fe nd ant i nte nd e d to imp or t or dis tr ibute kh a t w itha

c on tr oll e d s ub sta

nc e , w e sh are the Sixth Cir c uit ’s c on c e rn

re g ard ingc ri min a l st a tut e s th a t “ re ly on ob sc ur e te c hn ic a l or

sc ie nti fi c te rm s fore ign to or dinary

persons.” I d.

B. Su ff iciency of the Evid ence B e c a us e su ff ic ie nc y of the e vid e nc e is a

thr e sh old iss ue that ma

y ob viate oth e r c ha lle ng e s, see A llen, 127 F.3d at 264, we next ex amine Ha ssan’s conte ntion that the evidence was i n s u f f i c i e n tt o s u

p p o rth i s c o n v i c t i o n s o nth e th r e e kh a t - r e l a t e d c o n s p i r a c y c h ar g e s an d

th e f o rtyone substantive counts of mone y launder ing. 1. Stan dard of Revie w We reviewde novo cha lleng es to the suffic iency of the e vidence . United States v. Rang olan, 464 F.3d 321, 324 ( 2d Cir. 2006). To succ eed on suc h a cha lleng e, Ha ssan must satisfy
a “ he avy burd e n, ” Un ite d St ate s v . Sa nto s, 44 9 F .3 d 9 3, 10 2 ( 2d Cir . 2 00 6) , a s w e c on sid e r “ on ly ‘whe the r t he re c or d e vid e nc e c ou ld r e a so na bly su pp or t a fi nd ingof

g uil t be y on d a

re a so na ble doubt,’” United States v. Rodriguez, 392 F.3d 539, 544 (2d Cir. 2004) ( quoting Jackson v. Virg inia, 443 U.S. 307, 318 (1979)). We a naly ze the evidenc e in the lig ht most favorable to the prosec ution, crediting“eve ry infere nce that the jury

may have dr awn” in the g overnme nt’s favor
. United States v. Finley , 245 F.3d 199, 202 ( 2d Cir. 2001) (quoting United States v. Gore , 154 F .3 d 3 4, 40 (2 d Ci r. 19 98 )) . M or e ov e r, “ the g ov e rnme nt i s e nti tle d to pr ov e its c a se so le ly throug h circ umstantial evidence , provided, of c ourse, that the g overnme nt stil l demonstrates e ach
e le me nt o f t

he c ha rg e d o ff e ns e be y on d a

re a so na ble do ub t.” Rod

ri g ue z, 3 92 F .3 d at 54 4. Thus , we will uphold a convic tion so long as “ ‘any rational trier

of fa ct could have found the e ssential21

elements of the crime be y ond a re asonable doubt.’” I d. (quoting J ackson, 443 U .S. at 319). Neve rtheless, Ha ssan’s burde n, while heavy , is “not an impossible one.” United States v. Jone s, 39 3 F .3 d 1 07 , 1 11 (2 d Ci r. 20 04 ). “ [I ]f the e vid e nc e vie we d in the lig ht m os t f

avo ra ble to the prosec ution gives e qual or ne arly equal c ircumstantial support to a theor y of guilt and a theory of innoce nce, the n a re asonable jury must necessa

rily enter tain a re asonable doubt.” United States
v. Gl e nn , 3 12 F .3 d 5 8, 70 (2 d Ci r. 20 02 ) ( int e rn a l qu otatio n ma rk s o mitte d) . A ft e r a ll, “ ‘i t w ou ld not satisfy

the Constitut ion to have a jur y deter mine that the def

endant is proba

bly g uilty .’” Rodrigue z, 392 F.3d at 544 (quotingSulli van v. L ouisiana, 508 U.S. 275, 278 (1993) ( alteration marks omitted). 2. The Evidence was Sufficient to Con vict Hassan of the Kh at Con spiracy Charge “To sustain a c onspiracy

conviction, the g overnme nt must present some evidenc e fr om which it can r easona

bly be infe rre d that the per son char g ed with conspira cy knew of the exist ence of the sche me alleg ed in the indictment and knowing ly joined and par

ticipated in it.” Ro dr igu e z, 391 F.3d at 545 (internal quotation mar ks omitt ed). The g overnme nt need not show that a ny controlled substanc e wa s actua lly imported or distributed in order to convict a de fenda

nt of intentionally

participating in the c rime of c onspiring to import or distribute a c ontrolled substance
. Af te r a ll, “ imp os sib ili ty

of su c c e ss i s n ot a

de fe ns e .” Un ite d St a te s v . Jime ne z Re c io, 53 7 U .S. 270, 276 (2003) ( internal quotation marks a nd citation omitted). The esse nce of the cr ime of conspirac y

is “the agree ment to commit the crime.” I d. at 275. As we note d ear lier, khat may sometimes, but does not alway s, contain one or two stimul ants that are controlled substanc es under U.S. law: cathinone a

nd cathine. See 21 C.F.R. §§ 13 08 .1 1( f) , 1 30 8. 14 (e ); se e a lso 21 U. S.C. § 8 12 . In th is c a se , H a ssa n w a s c onvic te d o n tw o k hat-22

related conspira cy

char g es: conspira cy

to import cathinone, in violation of 21 U.S.C. §§ 952(a), 963, and conspira cy

to distribute and to possess with intent to di stribute cathinone, in violation of 21 U.S.C. §§ 841(a), 846. The g overnme nt’s evidenc e at tria l clear ly established, and H assan does not dispute, that Hassan know ingly conspired to import and distribute khat. There fore , Ha ssa n k ne w o f a nd kn ow ing ly

joi ne d a nd pa rt ic ipate d in

the sc he me a lle g e d. Th e on ly matte r i n dispute is whether the g overnme nt presente d evidenc e suff icient to demonstrate that Hassan “knowing ly

eng ag ed in the conspira cy with the specific intent to commit t he off enses that we re the objects of the conspirac y .” United States v. Samar ia, 239 F.3d 228, 234 ( 2d Cir. 2001), abrog ated on other

g rounds by

United States v. Huezo, 546 F.3d 174, 180 n.2 ( 2d Cir. 2008) (empha sis added). That is, beca

use “[c]onspiracy

is a specif

ic intent crime . . . [p]roof that the defe ndant knew that some c rime would be c ommitt ed is not enoug h.” United States v. Morg an, 385 F .3d 196, 206 (2d Cir. 2004) (inter nal quotation marks and c itation omit ted). A c onspiracy conviction cannot be sustained unless the g overnme nt established beyond a re asonable doubt that the defe ndant had the spe cific intent to violate the substantive statute. United States v. DiTommaso, 817 F.2d 201, 218 ( 2d Cir. 1987). Fur ther, if dire ct evidenc e is absent, “ [c] ircumstantial evidenc e of knowledg e and spe cific intent suff icient to sustain a conviction must include some indicia of the spec ific ele ments of the under lying c rime.” Sama ria, 239 F .3d at 235. Ther efor e, the g overnme nt could not meet its burden by offe ringevidenc e suff

icient to show that Hassa

n conspired to import or distribute khat; rather, the g overnme nt had the burde n of proving“beyond
a re asonable doubt that [ Hassan] ac tually knew that khat contained a controlled substanc e.” Caseer , 399 F.3d at 841 (emphasis adde d).23

As we pr eviously

explained, khat itself is not a controlled substance . See Ar g aw, 395 F.3d at 527 (“Khat is not a controlled substance ”); Husse in, 351 F.3d at 17 ( “The g overnme nt
c on c e de s th a t it

is n ot e no ug h to sh owthat th e a pp e lla nt k no wi ng ly po sse sse d k

hat.” ). Ins te a d, it is only “[w]hen khat contains cathinone, [t hat] khat is a Schedule I substance.” 58 Fe d. Reg . at 4317 (empha sis added). F urthermor e, the g overnme nt conce des on appe al that it was re quired, based on the indictment, to prove that Ha ssan knew he was de aling with khat containing
c a thi no ne , o r t

hat su bs tanc e by

so me oth e r, or

unkn ow n, name . We ho ld t he g ov e rnme nt t o th is
conce ssion. Theref

ore, in this case , the g overnme nt could not meet its burden by demonstrating that Hassan kne w he wa s dealingwith khat containingcathine, the chemica l ingr edient re g ulated by Schedule IV, but rathe r had to prove that Hassan kne w he wa s dealingwith khat containing cathinone. Cf. United States v. Morales, 577 F .2d 769, 776 (2d Cir. 1978) (“ [T] he law is settled that a def endant ne ed not know the e x act nature of a drugin his possession t o violate § 841(a )(1) ; it i s su ff ic ie nt t hat he be awa

re that he po sse sse s so me c on tr oll e d s ub sta nc e .” ). No ne the le ss, g ive n th a t w e mus t g ra

nt e ve ry inf e re nc e tha

t th e jur y may have dr awn

in f avo r o f t he g ov e rnme nt, we f ind that the g overnme nt -- bar ely -- met its burden of

providing evidenc e suff

icient to convict Hassan. What differe ntiates this case f rom the khat c ases that other circ uits have conf

ronted is that there was no dire ct evidenc e that any of the khat Hassan imported a ctually contained a

controlled
su bs tanc e – c athi no ne , in

thi s c a se . Cf

. Ca se e r, 39 9 F .3 d at 83 2; H us se in, 35 1 F .3 d at 12 . Wh ile the g overnme nt seized the khat imported by Hassan on the day

of his arr est, the g overnme nt failed to offer any evidenc e at tria l reg ardingthe che mical ana ly sis of this packag e of khat. Absent any dir e c t e vid e nc e of

c athi no ne imp or

tatio n, the g ov e rnme nt r e lie d o n c ir c ums tanti a l e vid e nc e to“This is not to sugg est that in all Controlled Subst ance s Act prose cutions the 7 g overnme nt must prove beyond a re asonable doubt that the defe ndant had a ctual knowledg e that the su bs tanc e at is su e is c on tr oll e d. F or su bs tanc e s su c h a s c oc a ine tha t are c on tr oll e d p e r s e under the controlled substanc es sche dules and for which ther e ar e no due pr ocess f air-w arning conce rns, construc tive knowledg e infe rre d from the listing of the substance in the controlled su bs tanc e s sc he du le s ma

y su ff ic e . H ow e ve r, wh e n a

targ e te d it e m, s uc h a s k

hat, i s n ot i tse lf listed in the controlled substance s schedules, due proce ss require s that the g overnme nt prove beyond a re asonable doubt that the defe ndant had a ctual knowledg e that the tar g eted item contained a

controlled substanc e re g ulated under fede ral drugabuse la

ws.” Case er, 399 F .3d at 842 n.8 (empha sis added). 24 establish Hassan’ s intent. See Samaria, 239 F .3d at 235. Althoug h the g overnme nt has no obligation to establish that the conspiracy was succ essful, the g overnme nt does bea r the burde n of proving , at a minimum, that there is evidenc e suff icient to prove be y ond a re asonable doubt that Hassan “ knew that he was de aling with a substance regulated by fede ral drugabuse la

ws,” cathinone spe cifica lly , as cha rg ed by the indictment. Hussein, 351 F.3d at 11; Caseer, 399 F .3d at 84 1 ( “ [T]o c onvic t [de fe nd ant] p ro pe rl y of the c ha rg e d o ff e ns e s, the dis tr ic t c ourt

wo uld ne e d to have f ound beyond a re asonable doubt that [ defe ndant] actually knew that khat contained a controlled substanc e.”)
. 7 Be cause of the lac k of direc t evidence , the g overnme nt sought to prove the re quisite intent in severa l way s. First, the g overnme nt presente d testimony about Hassa

n’s enc ounter with Ag ent Paul Kastava

at J FK in 2001; sec ond, it presented e vidence about Hassa n’s pre sence at a bond he ari ngfo r Ahme d M us sa ; and thi rd , it pr e se nte d e vid e nc e tha

t H a ssa n tr ie d to br ingthe kh a t in to the country

expeditious ly . Whil e all of this evidenc e indicate s that Hassan be lieved it was illeg al to import khat into t he United States, none of it, alone, supports what is required by law, i.e., “ that the def endant kne w he possesse d [t he] controlled substance [charg ed, cathinone], (even [if] he
wa s e ith e r m ist ake n a

bo ut o r d id n ot k

no w i ts e xac t id e nti ty

). ” Hu sse in, 35 1 F .3 d at 19 (e mph a sis25

added) . Neve rtheless, we are obligated to revie w all of the e vidence collectively , not to review
e a c hp i e c e o f

e v i d e n c e a l o n e . S e e U n i t e d S t a t e s v . A u tu o r i , 2 1 2 F
. 3 d 1 0 5 , 1 1 4 ( 2 d

C i r . 2 0 0 0 )
. It is with thi s understandingthat we r eview the evidenc e pre sented by the g overnme nt. Although ne ither the g overnme nt nor the district court ling ere d on this point , we be g in by noting that Ha ssan’s potential aw are ness, from his time living in Somalia, of the stimulant eff ect of khat wa s not enoug h to put him on not ice that khat contained c athinone, or inde ed some other controlled substanc e. Contra United States v. Sheikh, 367 F .3d 756, 763 (8th Cir. 2004). “Althoug h actua l knowledg e that a substanc e is controlled mig ht in some cases be inferr ed fr om the phy sic a l e ff

e c ts c a us e d b y the su bs tanc e , in

thi s c a se the sti mul ant e ff e c t of kh a t is too mil d to permit a re asonable infere nce that [ Hassan] knew that khat contained a controlled substanc e. . . . The see ming ubiquity

of cof fee houses in the United States attests to the fa ct that consuming p ro d u ct s wi ths t i mu l at i n g ef

fe ct s i s co m m o ncu s t o mi nth e U n i t edS t at es , an d th e a v er age Americ an cof

fee drinker most likely

does not pause to c onsider while dr inking his or he r morning ‘cup of J oe’ whether

he or she may

be subjec t to criminal sanction for posse ssion of a controlled substance.” Caseer , 399 F.3d at 843. Thus, ge nera l knowledg e of the fac t that khat contains ingr edients that ar e stimulants is not sufficie nt to raise eve n an infe renc e that Ha ssan knew that khat containe d cathinone. We now turn to the evidenc e that the g overnme nt argues supports the jury ’s findingthat Ha ssa n w a s guil ty

of c on sp ir ingto i mpo rt

and dis tr ibute c a thi no ne . F ir st, Ha ssa n w a s p re se nt at a bond hear ing f

or a f ellow khat importer, Ahmed Mussa. At that hea ring , importation of khat was ref err ed to at lea st twice as importation of a “drug ” and it wa s compare d to marijuana f or the purposes of se ntencing . Hassan pa rticipated in pa

rt of the he aring , beingasked to c ome to the26

front of the room to testify . A jury could re asonably

conclude that he wa s prese nt in the room when khat, drug s, and marijuana wer e re fer ence d. This is close to sufficient c ircumstantial evidenc e fr om which a jury could rationally

conclude that Hassan kne w that khat conta ined a controlled substanc e. Second, the g overnme nt argues that the spee d with which Hassa n attempted to bringthe kh a t in to t

he Un ite d St ate s and

the fa c t th a t he hir e d p e op le to h e lp h im g e t kh at out of Cus tom s quickly -- usingFuller ’s fra

udulent stamps to secure quick re lease of the pa ckag es and e mploy ing overnig ht delivery

service s -- indicate that he kne w he wa s importing the c ontrolled substance cathinone. T his evidence could have been c onstrued in light of testimony

that, over time,
c a thi no ne de g ra de s into w e ake r c he mic a ls. Tr ans po rt sp e e d is the re fo re dir e c tly re late d to
c a thi no ne ’s po te nc y , a

nd the fa ste r k

hat is sh ipp e d, the g re a te r t he pr ob a bil ity tha t it wi ll c on ta in cathinone when it arr ives at its intended destination. Combined with proof that Hassa n spent betwee n $3,000 and $4,500 a w eek to e nsure that the khat was imported with suffic ient speed, the jury was fr ee to infe r that Ha ssan intended to dea l not merely in khat, but khat with cathinone, sp e c if ic a lly . T he imp a c t of

thi s c umu lativ e e vid e nc e is w e ake ne d, ho we ve r, be c a us e the re is nothing in the r ecor d with respec t to how much time it actually took to ship t he khat to the United State s, i.e ., ho w muc h ti me ha d e la ps e d b e tw e e n th e mom e nt t he kh a t w a s p ic ke d in

No rt he a st Afric a and the time it arrived in the United States. N ever theless, it does aid the g overnme nt’s
c a se . F ur the r, be c a us e Ha ssa n’ s im po rt a tio n me tho ds inc lud e d e ff or ts t o c on c e a l th e natur e of his packa g es, the shippingevidenc e adds to Ha ssan’s pre sence at the bond hea ringto help show that Hassan kne w cathinone to be a r egulated substance
. Finally , the g overnme nt introduced e vidence that Hassan kne w khat could be seized atThe g overnme nt also proffe red “ evidenc e” that we do not believe supports its case that 8 Hassan w as guilty

of conspiringto import and distribute a Schedule I drug . The g overnme nt prese nted evidenc e that it tested seve ral pa ckag es of khat that were obtained af ter Ha ssan’s arr est, and the D EA che mist t estified that these packa g es conta ined both cathinone a nd cathine. Assuming a

rguendo both that the che mist’s testim ony was a dmissibl e as r eleva nt, and that DEA forms re cordingthe three additional seized packa g es we re a dmissibl e hea rsay -- two a ssumptions about which we have grave doubts -- this additional evidence does not help show eve n that Hassan intende d to import khat, nor does it support an infer ence that the seized pac kag es we re connec ted to the cha

rg ed conspira cy . The g overnme nt provided no evide nce, f or instance , about how these pa ckag es we re a ddresse d and labe led, from whe re the y wer e mailed, how longthey wer e in transit, or a

ny other infor

mation that would have pr ovided strong er c ircumstantial proof that these pa ckag es we re c onnecte d to Hassan And while Ag ent Kasta

va testified that he told Hassan that khat wa s illega l in the United State s - - a state me nt whic h is in f

a c t in a c c ur a te , a s k

hat is on ly

ill e g a l w he n it

c on ta ins a c on tr oll e d s ub sta

nc e -- he did

no t te sti fy

tha t he tol d H a ssa

n it wa s il le g a l be c a

us e it c ou ld contain contr olled substances, or more importantly , for the pur poses of this case , cathinone. A s such, this evidence has little use. 27 Customs . Of c ourse, “ [n] ot all items that may be seized by

the U.S. Customs Service s, howeve r,
are classified a s controlled substance s . . . .” Casee r, 399 F .3d at 844 (interna l quotation marks and citation omitted). Thus, while a jury could infer

from Ag ent Kastava’s testimony that Hassan “knew importation of khat violated U.S. customs laws,” it does not, alone , support the infer ence that Hassan “ knew he would be violating U.S. druglaws by importing” cathinone. I d. But it does add somethingto what a jury could infer

from Ha ssan’s pre sence at Mussa’s bond he aringand fr om h is atte mpt e d s pe e d in br ing ingkh a t to the Un ite d St a te s. 8 All this shoul d make c lear that we have dee ply

serious conc erns r eg ardingthe suffic iency of the e vidence in this case. We neve rtheless find that the e vidence -- whe n viewed c ollectively -- permits a findingof guilt. S ee Autuori, 212 F.3d at 114 (asser ting that we must “consider the evidenc e in its totalit y , not in isol ation”); United States v. Gua dag na, 183 F .3d 122, 130 (2d Cir. 1999). This is beca

use of our exceeding ly

defe rential standa

rd of r eview: we must analy ze the evidenc e in the lig ht most favorable to the prosec ution, ag ain cr editing “ ever y infere nce that the28

jury may have dr awn” in the g overnme nt’s favor . Finley , 245 F.3d at 202. We believe that whe n the e vid e nc e is v ie we d c oll e c tiv e ly -- e sp e c ia lly

Ha ssa n’ s p re se nc e a t Mu ssa ’s bo nd he ari ng , h is eff orts to avoid detec tion by law enf orce ment, and his manifest de sire to spee d the transit of khat into the United States -- ther e is sufficie nt circumstantial evide nce f rom which a

jury could have inf e rr e d th e re qu isi te sc ie nte r, i.e ., that H a ssa n k no wi ng ly int e nd e d to imp or

t and po sse ss w ith intent to dist ribute khat c ontaining c athinone. 3. The Evidence was not, However, Sufficient to Con vict Hassan of the Su bstant ive Money Laundering C

harges Ha ssa n w a s a lso c ha

rg e d w ithfo rt

y -o ne su bs ta nti ve c ounts of

mon e y la un de ri ng , in violation of 18 U.S.C. § 1956(a)(1) , based on mone y order s he purc hased be tween D ece mber 21, 1998, and May

15, 2000. To sustain the substantive money launder ing c harg es, the g overnme nt must establish that Hassan (1) knowing that the prope rty involved in a financ ial transac tion repr esente d the proc eeds of some form of unla

wful ac tivity , (2) c onducted or attempted to conduc t a fina ncial tra nsaction, (3) which in fa ct involved the proc eeds of specifie d unlawful a ctivity , (4) either w ith (a) the intent to promote the car rying on of

specifie d unlawful a ctivity or (b) the knowledg e that the tra

nsaction wa s desig ned at lea st in part to conce al or disguise the nature , location, source , owner ship, or control of the pr ocee ds of spec ified unlawf ul activity . See 18 U.S.C. § 1956(a); United States v. Gotti, 459 F.3d 296, 334 ( 2d Cir. 2006). The spe cified unlawful a ctivity

char g ed wa s “nar cotics traf ficking ,” in violation of 21 U.S.C. §§ 841(a)( 1), 846, and 963. The third re quirement is dispositive in thi s case . To sustain the substantive money launder ing c harg es, in stark c ontrast to the conspira cy char g es, the g overnme nt must show not29

simply that Hassan la

undere d money

that he believe d to be the proc eeds of cathinone sa les, but that the funds he la

undere d wer e in fa ct the proc eeds of cathinone sa les. As the g overnme nt
conce ded at or al ar g ument, “[w]e don’t have a ny seizures from that time per iod, so there’ s no direc t evidence ” to show that the unde rlying tr ansac tions actually involved the proc eeds of
c a thi no ne tr a ff

ic kin g . M or e ov e r, the re is n o c ir c ums tanti a l e vid e nc e to s ho w that H a ssa n a c tua lly traff icked in ca

thinone duringthis period. Instead, the g overnme nt relies on the a bundant evidenc e of H assan’ s khat-re lated ac tiviti es. F or instance , the g overnme nt argues that the money launder ing c harg es ar e supported by the notebooks and date books Hassa n kept detailinghis khat tr ans a c tio ns . In a dd iti on , th e g ov e rnme nt c on te nd s th a t th e fa c t th a t H a ssa n’ s d e c lare d in c ome
was a n amount far

less than the value of the money order s he purc hased suppor ts an infer ence that he used the proce eds of unr eporte d khat sales to purc hase the money order s. Howeve r, none of this evidence speaks to whe ther Ha ssan ac tually imported cathinone duringthis ti me per iod. Be cause cathinone c an disappe ar f rom khat in a matter

of day s, and must be imported fr om the Ho rn of Af ri c a or the Ar a bia n Pe nin su la , th e me re pr e se nc e of kh a t in the Un ite d St a te s c e rt a inl y does not support an infe renc e that ca thinone is present. See United States v. Muse, No. 06-c r-600, 20 07 WL39 15 63 , at *4 (S .D .N .Y . Jan . 3 0, 20 07 ); Ar g aw, 39 5 F .3 d at 52 6 ( “ [W]itho ut s c ie nti fi c te sti ngon a c a se -b y -c a se ba sis , it

c ann ot b e de te rm ine d w he n c a thi ne or c a thi no ne a

pp e ars in khat.”) . The c ircumstantial evidenc e that the g overnme nt presente d does not, in any way , support an infe renc e that Ha ssan’s proc eeds w ere the re sult of the specifie d illega l activity , i.e., the importation of cathinone. T hus, the substantive money launder ing c harg es ca

nnot be sustained. We theref ore r ever se the judg ment of the district cour t, and the ca se is rema

nded with instructions to e nte r a jud g me nt o f a c qu itt a l on a ll f or ty -o ne su bs tanti ve c ounts of

mon e y la un de ri ng , in30

violation of 18 U.S.C. § 1956(a)(1)
. 4. The Evidence was Sufficient to Con vict Hassan of Cons pirin g to Laun der Money. Hassan w as also cha

rg ed with one c ount of conspira cy to launder mone y , in violation of 18 U.S.C. § 1956(h). “In order to establish that a def

endant c onspired to launder monetary instruments in viol ation of 18 U.S.C. § 1956(h), the g overnme nt must show that the defenda nt ag ree d to: 1) conduct a

financ ial transac tion; 2) involvi ng the proc eeds of specifie d unlawful
a c tiv ity ; 3) kn ow ingthat th e pr op e rt y inv olv e d in

the tr ans a c tio n r e pr e se nte d th e pr oc e e ds of so me form of unla

wful ac tivity ; and 4) knowingthat the financ ial transac tion was desig ned in whole or in p art to c on c e a l or

dis g uis e the natur e , s ourc e , lo c a tio n, ow ne rs hip , o r c on tr ol o f t ho se proce eds.” United States v. Henry , 325 F.3d 93, 103 ( 2d Cir. 2003). The e vidence prese nted at trial wa s sufficient to sustain a c onviction on this count, which char g ed Ha ssan with conspiringto launder mone y “betwe en De cembe r 1998 and A pril 2003.” [A 36] The money

order s, unrepor

ted income, date books, and notebooks a llowed the jury to infer that Hassan a g ree d to conduct var ious financial tra nsactions, knowingthat the transa ctions were structure d to disguise the na ture a nd source of the funds involved. H avingfound the e vidence
su ff ic ie nt t o c onvic t H a ssa

n o f t he c athi no ne c on sp ir a c y

c ha rg e s, the jur

y c ou ld h ave e a sil y inferr ed that Ha ssan believe d that the funds re lated to cathinone traff icking . Be cause the g ov e rnme nt p re se nte d mo ne y or de rs purc ha se d b y

Ha ssa n in No ve mbe r 2 00 2, a ft e r h is participation in the bond hearingand followinghis encounter with Ag ent Kastava, the jury was able to also c onclude that Ha ssan knew c athinone wa s a re g ulated substance duringthe per iod char g ed in the indictment. Howe ver, a s we e x plain below, we believe the re w as a f undamental and pre judicial err or in the district court’ s instructions to the jury on scienter . Be cause we f ear31

that this error ma

y have a ffe cted the jur

y ’s deter mination on this issue, we va cate the judg ment of the dis tr ic t c ourt , a

nd re mand fo r a re tr ia l on the on e c ount o f c on sp ir a c y to l a un de r m on e y , in vio latio n o f 1 8 U .S. C. § 19 56 (h ). F or the same re a so ns , d isc us se d in fu rt he r d e ta il b e low , w e a lso
va c a te the jud g me nts on

the on e c ount o f c on sp ir a c y to i mpo rt c a thi no ne , in

vio latio n o f 2 1 U .S. C. §§ 95 2( a ), 96 3, and

the on e c ount o f c on sp ir a c y to d istri bute and

to p os se ss w ithint e nt t o distribute cathinone, in violation of 21 U.S.C. §§ 841(a), 846.

C. Er r one ous Jur y I nst r uc ti ons 1. Stan dard of Revie w We reviewde novo a c laim of err or in jury instructions, “reve rsing only wher e, viewing the cha rg e as a whole, ther e wa s a pre

judicial err or.” United States v. Aina-Ma rshall, 336 F.3d 167, 170 (2d Cir. 2003). Howe ver, the g overnme nt contends that her e de novo r eview is not appropr iate. Rather , the g overnme nt asserts that a pla in error standard a

pplies, beca

use Ha ssan failed to pre sent his challeng e to the cha rg e on intent to the district court. See , e.g ., United States
v. Mil le r, 11 6 F .3 d 6 41 , 6 72 (2 d Ci r. 19 97 ). We d isa g re e , a nd ins te a d f ind tha t de no vo re vie w i s appropr iate. The g overnme nt’s claim swee ps too broadly . At the cha rg ing c onfer ence , defe nse counse l clea rly raised a n objection to the jury

instructions that dealt with prec isely the issues now bef

ore us. Wi th respec t to CountOne, importation, def ense c ounsel stated: The only controlled substanc e involved in this case is c athinone. I f it’s not cathinone, w e’ve stipulated cathine c ould not be reg arde d, khat is not a controlled substance. I

don’t know-- they

can’ t argue her oin or coc aine. The re is no evidenc e of a

ny thing other

than cathinone. This . . . broade ns it so wide. . . . Ijust thi nk the sentenc e should be de leted.32

. . . The off

icer sat on the stand, testified that khat was a c ontrolled substance
. . . . The c hemist witness went furthe r, he e ven said c athine, I found cathine, and it’s on schedule f

our. . . . What if the jury

hear d that and they

say oh that cathine business, it mi g ht have be en cathine. Hassan’ s trial counsel thus made c lear that he believe d that portions of the jury char g e should be str ic ke n s o a s to a ssu

re that th e jur

y did no t c onvic t H a ssa

n, imp ro pe rl y , o n th e ba sis of his conspiringto import “some controlled substanc e” othe r than c athinone. Althoug h Hassan did not expli citly reiter ate his objec tion to the jury instruction relatingto Count I I , the same c harg ing l an gu age wa s ati s s u e i nb o thdru g co un t s . T h er e w as n o re as o nfo r H as s an t o l i m i th i s ch al l en ge to C ount I , n or

fo r t he c ourt to b e lie ve he wa s d oin g so . It is tr ue tha t, a s th e g ov e rnme nt a

rgue s, if Ha ssa n h a d s pe c if

ic a lly ob je c te d to the c ha

rg e fo r C ount I I , th e c ourt may have ma de the same mod if ic a tio ns to t

he sc ie nte r i ns tr

uc tio n a s it

did fo r C ount I . H ow e ve r, tha t is imm a te ri a l on

thi s appea l, beca

use Ha ssan is arguing that -- eve n as modified -- the cha rg e for Count Iwas
err oneous. The g overnme nt also claims that the ar g uments beingraised on a ppeal a re not pre serve d beca use trial counse l, after

objectingto the jury

instructions, failed to propose a lternative languag e. This ar g ument also fails. Rule 30(d) r equire s only that a par ty “inform the c ourt of the sp e c if ic ob je c tio n, ” F e d. R. C ri m. P . 3 0( d) , a nd do e s n ot r e qu ir e tha

t a pa rt y pr op os e a lte rn a te langua g e in o rd e r t o p re se rv e a c ha lle ng e fo r a

pp e a l. A s th e c ite d p or

tio n o f c ouns e l’ s st a te me nts indicates, the substanc e of the claim now beingraised on a ppeal wa s square ly

raised be low:
c ouns e l ma de it c le ar t o th e tr ia l c ourt that he ob

je c te d to the c ha

rg e be c a us e he be lie ve d it permitted the jury

to convict Hassa

n based on a

finding that Hassan intende d to import and distribute khat or khat c ontaining c athine. Cf. United States v. Masotto, 73 F .3d 1233, 1237-3833

(2 d Ci r. 19 96 ) ( c on c lud ingthat sp e c if ic ob je c tio n w a s p re se rv e d s o lo nga s c ouns e l’ s a rgume nts
wer e “suf ficient to direc t the district court to his contention,” eve n if counsel f ailed to mention the specific languag e he w as re questing ); see a lso 2A Charles A. Wrig ht et al., Fe dera l Practice & P ro ce d ure § 4 8 4 (3 d

ed
. 2 0 0 0 ) ( “A p arty

m ay o b j ec tt o an i n s tru ct i o ngi v en b y th e c o urt al th o u gh it has not requeste d an instruction of its own on the point.”); United States v. Eng lish, 409 F.2d 20 0, 20 1 ( 3d

Cir . 1 96 9) (“ [W]e n ote that c ouns e l’ s e xce pti on to t he c ha rg e , a lth ou g h n o r e qu e sts fo r c ha rg e we re su

bmi tte d, wa s su ff

ic ie nt t o p re se rv e the e rr or fo r a ssi g nme nt o n a

pp e a l.” ). Thus , we r eview de novo Hassan’ s claim that there was pre judicial err or in the jury

instructions. 2. The Di stric t Co urt M

ad ea Fun da menta l Erro r in i ts J ury Ins truc tio ns “A jury instruction is errone ous if it mis leads the jury as to the cor

rec t leg al standar d or does not ade quately

inform the jury

on the law.” Ander son v. Br anen, 17 F .3d 552, 556 (2d Cir. 1994). Ther efor e, “[a]n errone ous instruction, unless harmless, re quires a ne w trial.” I d. “An
err or is harmless only

if it is clear be y ond a re asonable doubt that a rational jury would have f

ound the def endant guilty

absent the e rror .” United States v. Quattrone, 441 F .3d 153, 177 (2d Cir. 2006) (quotingUnited States v. Carr, 424 F .3d 213, 218 (2d Cir. 2005) (inter nal quotation marks omitted)). We beg in by

noting that, in this case , the instruction to the jury on the re quirement of intent is critical for two r easons. F irst, as noted above , scienter is what prese rves the r eleva nt statutory and re g ulatory

scheme from a suc cessf

ul due proc ess cha lleng e. Second, H assan ha s been c harg ed only

with conspirac y , and thus the g overnme nt does not need to prove that Hassan
ever actua lly imported or possessed c athinone with intent to distribute, but only that he intended to d o s o. Se e Un ite d St ate s v . M or g an, 38 5 F .3 d 1 96 , 2 06 (2 d Ci r. 20 04 ) ( “ Con sp ir a c y is a34

specific intent crime . . . .” ); United States v. Soto, 716 F.2d 989, 993 (2d Cir. 1983) ( stating that the g ov e rnme nt m

us t “ e sta bli sh [] be y on d a

re a so na ble do ub t th a t th e de fe nd ant h a d th e sp e c if ic intent to violate the substantive statute[s] ” cha rg ed as the object of the conspirac y (citation omitted)). In a conspira cy case , “[p] roof that the de fenda nt knew that some c rime would be committed is not enough.” Morg an, 385 F .3d at 206 (c itation omit ted). Count One cha

rg ed Ha ssan with conspiringto import cathinone, a Sche dule I controlled substance, in violation of 21 U.S.C. §§ 952(a) , 963. As to Count One, the district court instructe d the jur y that in or de r t o c onvic t H a ssa

n, the jur y “ mus t f ind that th e de fe nd ant k

ne w i t w a s a controlled substanc e he w as conspiringto bring into the United States,” and e x plained that the jury “nee d not find that the defe ndant knew or believed tha

t it was a drugcalled c athinone, as long as the g overnme nt proves that he kne w and intende d that some controlled substanc e would be imp or te d into t he Un ite d St ate s. ” Count T wo c ha rg e d H a ssa

n w ithc on sp ir ingto p os se ss w ith intent to dist ribute cathinone in violation of 21 U.S.C. §§ 841(a)(1), 846. A s to Count Two, the district court instructed the jury that, in order to c onvict Hassan, the jury had to find that Ha ssan “ac ted with the spec ific intent of possessingthe controlled substanc e,” a nd explained that “[t] he g overnme nt need not, howe ver, pr ove that the de fenda nt knew the e x act nature of the controlled substance in his possession. I t is enoug h that the g overnme nt proves that the de fenda nt knew that he possessed some kind of a c ontrolled substance .” Ha ssa n a rgue s th at th e c ha

rg e s to the jur

y on the c on sp ir a c ie s to imp or t and dis tr ibute cathinone w ere err oneous and not a ccur ate e x planations of the law , beca use they left open the possibili ty

that the jury

could convict Ha ssan on an imprope r basis -- either on the basis that he intended to import and distribute khat (whic h is not a controlled substance ) or on the ba sis that heDef ense c ounsel ac tually

highlig hted some of this testimony when objec ting to the jury 9 ins tr uc tio ns , b ut t

he jud g e ind ic ate d th a t a

law e nf or c e me nt o ff

ic e r’ s te sti mony

that kh a t w a s a controlled substanc e wa s a matter “ for the jur y .” We ar e troubled by

this comment; reg ardle ss of 35 imported or distributed cathine (which, a s the g overnme nt has ac knowledg ed, wa s not the controlled substanc e which H assan wa s char g ed with possessing in the indictment). Hassa n points out t hat the district cour t did not ex plain to the jury that khat itself is not a controlled
su bs tanc e , o r t

hat de fe nd ant’ s inte nt t o im po rt or po sse ss k

hat c ou ld n ot b e the ba sis fo r h is conviction without proof that he intende d to import or possess khat with cathinone. F urthermor e, the district court did not explain to t he jury that cathine is a

differ ent, and less se rious controlled substance, a

nd could not be the ba sis for Hassa n’s conviction of the crimes c harg ed in the indictment. Ha ssa n c on te nd s th at th e pr ob le ms w iththe jur y ins tr uc tio ns are of

pa rt ic ula r i mpo rt , beca use at trial, g overnme nt witnesses repe atedly sug g ested -- incorre ctly , and without corr ection by the cour t -- that khat itself is a c ontrolled substance . Be cause khat is not, per se, a controlled
su bs tanc e , th e dis tr ic t c ourt ru le d b e fo re tr ia l th a t th e “ [g ]ove rnme nt w ou ld n ot b e pe rm itt e d to introduce e vidence that khat is per se a contr olled substance.” Nonethele ss, at trial numerous g overnme nt witnesses sug g ested that khat was in fac t a controlled substanc e. F or example, Special Ag ent Kastava testified that khat is “an illeg al substance in the United States,” Spec ial Ag ent L ee te stified that khat is a “na rcotic” and “is on the c ontrolled substance list,” Special Ag ent Villanucc i testified that he ar rested H assan f

or “[i] mportation of khat” a nd arr ested a

nother ind ivi du a l e arl ie r f

or “ atte mpt ingto i mpo rt

kh a t,” F ull e r t e sti fi e d th a t he ple d guil ty to “[c]onspi rac y

to import khat,” and that khat is “a controlled substanc e,” a nd Mohamed Ha ssan testified that he pled guilty to importing “f

orbidden stuff . . . [t]he khat.” Fur thermore , a 9how the leg al status of khat is cha rac terized, it is a leg al issue for the judge to decide, a nd clar ify for the jur y , not a question of fa ct re serve d for the jur y . 36 g overnme nt witness also discussed the illeg ality of khat with cathine. Specifica lly , the DEA chemist testified that khat may contain cathine, that cathine is a Schedule IV controlled substanc e, and that the khat tested in connec tion with thi s case in fac t contained both cathine and cathinone. Despite this repe ated testimony , the district court did not clar ify to the jury

that Hassan w as
c ha rg e d w ithimp or

tin g or po sse ssi ngkh a t w ithc a thi no ne , n ot k hat, n or kh a t w ithc a thi ne . T hu s, Hassan a rgues that these statements by witnesses, combined w ith the jury instructions, allowed the jury to believe that it could convic t Hassan be cause he intended to import and posse ss khat, or intended to import and possess khat with cathine. Th e g ov e rnme nt m ake s a numbe r o f a

rgume nts c on c e rn ingthe e vid e nc e in t his c a se . F ir st, the g overnme nt argues that Ha ssan misreads the jury instructions, taking one sentenc e out of
c on te xt, and

that a re vie w o f t

he e nti re c ha

rg e sh ow s th a t H a ssa

n’ s a rgume nt h a s n o me ri t. Wh ile the g ov e rnme nt c on c e de s th at w itn e sse s te sti fi e d th a t kh a t is an unla wf ul c on tr oll e d s ub sta

nc e , it nonetheless dismisses this testim ony as “not litera lly

false” g iven the fa ct that khat is a c ontrolled substance when it contains either cathinone or

cathine, like the khat at issue. B ut cf. Ar g aw, 395 F.3d at 527 (“[k] hat is not a controlled substanc e”) ; Hussein, 351 F.3d at 17 (“B ut khat, unlike
c oc a ine , is no t a

c on tr oll e d s ub sta

nc e pe r s e , a

nd the g ov e rnme nt c on c e de s th a t it is n ot e no ug h to show that the appe llant knowingly possessed khat.” ); 58 Fe d. Reg . at 4317 (“ When khat contains cathinone, kha

t is a Schedule I

substance;” and “[w]hen khat does not conta in cathinone, but does contain ca

thine, khat is a Schedule I V substance .”). The g overnme nt also claims that the DEA chemist corr ecte d any

such misconce ption by

testifying “ unequivoca lly ” that khat wa s not on the37

c o n tr o l l e d

s u b s t an c e s l i s t . W e d i s a g r e e w i thth e g o v e r n m e n t ’ s c h ar a c t e r i z a t i o no f th i s t e s t i m o n y; to the contra

ry , we be lieve that Ha ll’s testimony was c lear ly

equivoca l. When asked whe ther khat, the plant, wa s on the controlled substanc e list, he replied, “No, it’s not. Not that Iknow of.” Moreove r, the jury

was still free to weig h Hall’s testimony ag ainst the misleading testimony of the oth e r g ov e rnme nt w itn e sse s, inc lud inglaw e nf or c e me nt o ff

ic e rs , a nd c ou ld h ave re a so na

bly
rea ched the conclusion that khat wa s, in fact, a controlled substanc e. But the que stion before us is not, as the g overnme nt sugg ests, whether this trial testim ony
wa s li te ra lly

fa lse , b ut r athe r whe the r, in l ig ht o f t he te sti mony , th e jud g e ’s ins tr uc tio ns fa ile d to pr e se nt t he jur y wi th a c or re c t e xplanatio n o f t

he law. Th e g ov e rnme nt a rgue s th a t H a ssa

n ta ke s a sin g le se nte nc e in t

he jur y ins tr uc tio ns out of

c on te xt an d th a t th e c ha

rg e a s a wh ole pr op e rl y instructed the jury

that an ele ment of ea ch cha rg ed cr ime was the intent to import or possess the controlled substanc e cathinone, reg ardle ss of whethe r Ha ssan knew the substance by name. The g ov e rnme nt i s c or

re c t th at r e fe re nc e s to c a thi no ne a pp e ar f re qu e ntl y in t he jur y ins tr uc tio ns : [R eadingfrom the indictment:] “Count One: Conspiracy to I mport Cathinone. . . . [defendant] did knowingly and intentionally

conspire to import into the United States . . . a substance containingcathinone. “I instruct y ou that cathinone is a controlled substanc e under the law a nd for the purposes of the se statutes.” “B efor e you may

convict the de fenda

nt of conspira cy

to import cathinone as char g ed in the indictment, the g overnme nt must establish each of the following elements be y ond a re asonable doubt.” “[Y]ou need not find that the defe ndant knew or believed that it was a drugcalled c a thi no ne , a s lo nga s th e g ov e rnme nt p ro ve s th a t he kn e w a nd int e nd e d th a t so me controlled substanc e would be importe d into the United States. As Itold y ou ear lier, cathinone is a controlled substanc e.” [F ro m th e ind ic tme nt: ] “C ount T wo : Co ns pir a c y to P os se ss w ithInte nt t o Di str ibute Cathi no ne . . . . [de fe nd ant] d id k no wi ng ly and int e nti on a lly

c on sp ir e to distribute and possess with intent to dist ribute a c ontrolled substance , which offe nse involved a substanc e conta ining c athinone . . . .” “I have a lrea dy

instructed you that cathinone is a controlled substanc e under the38

law.” “[Y]our decision as to whether the def endant c onspired to commit a par ticular un lawf ul a c t, e ith e r d istri butio n o f c a thi no ne or po sse ssi on

wi th i nte nt t o distribute cathinone, must be una nimous.” “The elements of posse ssion with int ent to distribute are : First, that the def endant possessed cathinone; Second, that the def endant kne w that he possesse d a c on tr oll e d s ub sta

nc e ; and Th ir d, that th e de fe nd ant p os se sse d c a thi no ne wi th intent to dist ribute it.” “The elements of the crime of distribution of cathinone ar e: Fir st, that the defe ndant distributed cathinone; Sec ond, that the def endant distributed the cathinone know ingly .” Moreove r, cathinone is the only controlled substanc e identified in the jury instructions. The g overnme nt theref

ore a rgues that the purpose and the e ffe ct of the jury instruction was to inform the jury

that Hassan ne ed not know that the c ontrolled substance at issue was na med cathinone, so longas Ha ssan re alized it was a controlled substanc e. While we agree that this was likely the district court’s pur

pose in stating the jury

instructions as it did, we disag ree with the g ov e rnme nt a s to the e ff

e c t th at th e ins tr

uc tio ns may

have ha d. We e mph a size , a g a in, that in thi s
c a se the sc ie nte r r e qu ir e me nt i s w hat pr e ve nts the e nti re re g ulator y sc he me , a s it

re late s to kh a t, from beingunconstitutional. Theref ore, w e must scrutinize the instructions reg ardingscienter , and the c ontext in which they wer e g iven, ver

y closely . Her e, we believe that the jury instructions failed to c orre ctly

inform the jury

that a bar e intent to import or possess khat, or khat with cathine, would not be suffic ient to sustain Hassan’s c onviction. I nstead, in lig ht of the evide nce pr esente d to the jury

throug hout the trial, the jury may have ve ry

well convicte d Hassan on the err oneous belief that khat is a controlled substanc e, or on the basis of a be lief that Ha ssan must have known, at a minimum, that he was importing with intent to dis tribute cathine. We theref ore f ind that there
was a fundame ntal err or in the jury instructions. Further

more, g iven how close we be lieve the sufficie ncy

of the e vidence was in this case , and the e ssential role that the sc ienter r equire ment39

pla y e d in our d ue pr oc e ss a

na ly sis , th is e rr or

wa s n ot h arm le ss. We are also unpersua ded by the g overnme nt’s rema ining a rguments. First, the g ov e rnme nt a

rgue s th at th e c ha

rg e a s a wh ole wa s a de qu a te be c a us e c a thi no ne wa s th e on ly substance ide ntified as a c ontrolled substance in the jury char g e. While this i s so, as we e x plained above in de tail, the jury

also hea rd inac curate testimony

to the eff ect that khat is il leg al, along with acc urate testimony

that cathine is a lso ill eg al. The district c ourt’s jury instruction thus left open the possibility

that the jury

would convict on one of

these a lternative ba ses. Second, the g overnme nt argues that it is inconceivable that Hassan intende d to import any thing other

than cathinone in lig ht of his overnig ht delivery methods. This is obvious ly not true. Ha ssan’s customers may

have pr efe rre d fre sh khat containingcathine, or simply fre sh khat containingno controlled substanc es. De spite the expedited means of de livery , there was a bsolutely no evidenc e in the rec ord of whe n the khat ar rived, much le ss that it arrived in the United States w ithin 48-72 hours of it beingcut. See U.S. Dr ug Enforc ement Administration, Fa ct Sheet, Khat, AKA: Catha Edulis, http: //www.dea .g ov/pubs/pressrel/pr072606a .html (last visi ted Aug . 10, 2008)(statingthat “[c]athinone . . . dissipates within 48 hours of harve st”); FD A Report 11-12 ( stating that khat leave s have be en re ported to lose their e ffe ct within three da y s of har vesting ). Finally , and per

haps most troubling, the g overnme nt cites our dec ision in Unit ed States v. Mo ra le s, 57 7 F .2 d 7 69 , 7 76 (2 d Ci r. 19 78 ), to a rgue that H a ssa

n c ou ld h ave be e n la

wf ull y
c onvic te d b y

the jur y e ve n if the jur y fo un d th a t he int e nd e d to imp or t an il le g a l su

bs tanc e wi th cathine, a nd not an illeg al substance with cathinone. F irst, as stated pre viously , we be lieve the jury instructions, in li g ht of testimony at trial, cr eate d a re al possibilit y that the jury

may have convicted H assan on the e rrone ous belief that khat, itself, was a c ontrolled substance , and40

there fore this argument is unpersuasive. Sec ond, the g overnme nt conce ded at tria l that it was not trying a n “any” contr olled substance c harg e, but rather, wa s limi ting itself to try ing acathinonere late d c ha

rg e , a s li ste d in

the ind ic tme nt. Mo re ov e r, the g ov e rnme nt’ s atte mpt to u se Mo ra le s to argue that any

err or in the jury

instructions was har

mless runs square ly

into Hassan’s c onstructive amendment c laim. A conviction base d on cathine, r ather than cathinone, would have be en an impermissible constructive amendment of the indictment. See United States v. Woz niak, 126 F.3d 105 ( 2d Cir. 1997) (holding that an instruction per mitti ng the jury

to convict on the basis of
mari jua na tr ans a c tio ns , w he n in dic tme nt a lle g e d o nly c oc a ine and

me tha mph e tamin e tr ans a c tio ns , was a n impermissible constructive amendment of the indictment). Under Mor ales, the g overnme nt could have c harg ed this case as one involvingeither c athinone or c athine, or both. Howeve r, the g overnme nt made the de liberate choice to indict Hassan with conspiringto import and possess cathinone; we assume, be cause it wanted to invoke the ha rsh pena lties applicable to a Schedule I

controlled substanc e. B y makin g thi s c ha

rg ingde c isi on , H a ssa

n’ s a lle g e d inte nt t o im

po rt and po sse ss t his Schedule I

substance w as cr itical to a conviction. See Wozniak, 126 F.3d at 109. “ [A] defe ndant has the rig ht to be tried only on char g es conta ined in an indictment re turned by a g rand jury . An unconstitutional amendment of the indictment occ urs when the char g ing te rms are altere d, either literally or construc tively .” I d. (interna l quotation marks and citation omitted). Constructive amendments a

re “ per se violation[ s] of the Grand Jury Clause of the F ifth Amendment that require [] reve rsal eve n without a showing of pre judice to the def

endant.” I d. (interna l quotation marks and c itation omit ted). Ha ssan’s intent was a n essential ele ment of the off ense, a nd an impermissible constructive amendment of the indictment oc curs if the impermissible alteration41

“af fec t[ s] an essential element of the offe nse.” United States v. Patino, 962 F.2d 263, 266 (2d Cir. 1992). The jur

y char g e, which c ompletely failed to e x plain the unique re g ulatory scheme , and allowed the jur

y to convict if Ha ssan conspire d to import or distribute “some controlled substance,” simply

does not satisfy

the burde n assumed by

the g overnme nt in this case . There fore , we va cate the judg ment, and re mand for a new tria l. We understand that the khat-related re g ulatory scheme poses unique and c omplicated iss ue s f or the g ov e rnme nt, de fe nd ants , a nd dis tr ic t c ourt s. We a

re no t un sy

mpathe tic to t

ho se problems. In this case, howe ver, g iven the ter ms of the indictment, the misleadingevidenc e allowed at trial conce rningthe illeg ality of khat, a nd the potentially

confusingevidenc e
conce rningcathine, the jury instructions were clea

rly err oneous. F urthermor e, the jury i n s tru ct i o n s we re n o th arm l es s . Un d er th e c i rc u m s t an ce s o f t h i s ca s e, t o b e v al i d , th e j ury ch ar ge neede d to expl ain explicitl y to the jury

that (1) khat itself is not a controlled substance and Ha ssan
c ann ot b e c onvic te d s imp ly fo r i nte nd ingto i mpo rt

or po sse ss w ithint e nt t o d ist ri bute kh a t; ( 2) if the jur y fo un d th at H a ssa

n h a d th e int e nt t o im

po rt and po sse ss k

hat w ithc a thi ne , th a t to o w ou ld
no t be su ff

ic ie nt t o c onvic t H a ssa

n; a nd (3 ) t hat th e g ov e rnme nt i s b ound by the sc ie nte r b ur de n it assumes in the cr imes it charg es -- the g overnme nt was re quired to prove here that Hassan ha d the intent to import and possess khat with cathinone.

D. Re mai n i n g Cl a i ms We are reve rsing and orde ringan entr y of ac quittal on forty -one of Hassan’ s substantive
mon e y la un de ri ngc ha

rg e s, and va c atin gand

re mand ingto t

he dis tr ic t c ourt

fo r r e tr ia l on

a ll
rema ining c harg es. Ther efor e, we need not c onsider Ha ssan’s re maining a rguments that he wa s42

de nie d a fa ir tr ia l be c a us e the g ov e rnme nt f

a ile d to c or

re c t f a lse and mis le a din g te sti mony , h is trial counsel wa s ineffe ctive, the district cour t erre d in admitting the DEAchemist’s testimony and the e x hibits reg ardingthe testing of three samples of khat, and that his sentence was
err oneous and unr easona

ble.

III . C ON CL USI ON Be cause we c onclude that the e vidence was insuffic ient to convict Hassa n of the for

ty -one substantive counts of money launder ing, in violation of 18 U.S.C. § 1956(a) (1), we REVERSE the judgme nt on these counts, and dir ect the district c ourt to enter a n order of ac quittal. Bec ause w e believe the re w as a f

undamental e rror

in the jury

instructions that was not harmless, we VACATE Hassan’ s conviction on the re maining c ounts and rema nd to the district court for retria l, if the g overnme nt should wish to pursue the matter.