FI L ED U.S. COURT OF A P P E A LS E LE V EN T H C IR C U IT J ULY 21, 2006 THOMAS K. KAH

N CL ERK [PUBLIS H] IN THE UN ITED STATES COURT OF APPEALS FO R T HE EL EV EN TH CIRC UI T

____ ____ ____ ____ ____ ____ N o. 05- 1320 5

____ ____ ____ ____ ____ ____ D. C. Dock etNo. 0 4- 00 11 1- CR-OR L-31 -J GG UNITED STAT ES OF AMERIC A, Pl ai nti ff -Appe llant, ve rs us AA RONER IC W IL LI AMS , De fendant-Appellee.

____ ____ ____ ____ ____ ____ Appeal f rom the United State s District Court fo r the Mi ddl e D istri ct

of F lor ida

____ ____ ____ ____ ____ ____ _ (J ul y 21 , 200 6)

Be fo re BL A CK , P RY O R and C O X , Ci rc uit Jud ge s. BL ACK , C ircuit Judg e:2

The G overnm ent appeals Aaron Er ic W illiam s’ 204-m onth sentence im pose d f or pos se ssi ng c ra ck

c oc ai ne w ithint en t t o di str ibu te , in vio la tio n of 21 U . S. C. § 84 1( a) (1 ). W e co nc lud e the dis tr ic t c ourt e rr ed in m iti ga tin g W ill iam s’ se nte nc e ba se d on( 1) it s ge ne ra liz ed dis ag re em en t w ithCo ngr es s’ s po lic y of puni shing cra ck cocaine off enders m ore severe ly

than powder cocaine of

fenders through the 100-to-1 crack-to-powder drug quan tity ratio, (2) its generalize d dis ag re em en t w iththe G uid el ine s c ar ee r of fe nde r enhanc em en t, U . S. S. G . § 4B 1. 1, an d ( 3) it s be lie f that the G ove rn m en t m an ipu la te d W ill iam s’ se nte nc e by arrangin g to pu rchase c rack c ocaine instead of powder coca ine. W e further co nc lud e that the se e rr or s are not harm le ss b ec au se W ill iam s ha s f ai le d to m ee t hi s bur de n of sho w ing that, c onsi de ri ng the r ec or d a s aw hol e, the e rr or s di d no t have a subs tanti al e ff

ec t onthe c ourt’ s c hoi ce of se nte nc e. W e, the re fo re , va cate the s e n t e n c e a s u n r e a s o n ab l e an dr e man df o r th e d i s tr i c tc o u rtt o s e n t e n c e Wi l l i a ms ba se d onthe ind ivi dua liz ed f ac ts and c ir cum stanc es of W ill iam s’ c as e be ar ing up on th e se nt en ci ng co ns id erat io ns en um erat edin 18 U.S.C. § 3 55 3( a). I. BACKG ROUND InApr il 2003 , ac onf

ide nti al inf

orm an t t old

D ru g E nf

or ce m en t Adm inistration (D EA ) agents and Osce ola CountySherif f’ s Deputies that W illiam s was selling crac k cocaine fr om his hom e in Kissim

m ee, Florida. BasedWil liams sold the undercove r ag ent 4.6 g rams of c rac k coca ine in April, 10.1 g rams of 1 c r a c k c o c a i n e i nM ay, an d

2 0 . 1 g r am s o f

c r a c k c o c a i n e i nJ u l y. 3 on this ti p, D E Aa ge nts ini tiate d asti ng o pe ratio n to pur ch as e cr ac k c oc ai ne f ro m W ill iam s w iththe he lp o f the c onf ide nti al inf

orm an t. I n th re e se parate transactions in April, May , and Jul y of 2003, an undercover D EAagent purchased a tot al of 34. 8 gr am s of

c ra ck c oc ai ne f ro m W ill iam s. Agr an d j ur

y sub se que ntl y 1 ind ic te d W ill iam s f

or one c ount

of pos se ssi ng c ra ck

c oc ai ne w ithint en t t o dis tr ibu te , in vio la tio n of § 84 1( a) (1 ) an d ( b) (1 )( C) , and tw o c ount s of pos se ssi ng fi ve or m or e gr am s of

c ra ck c oc ai ne w ithint en t t o di str ibu te , in vio la tio n of § 841 (a)( 1) and (b)(1)( B)(iii). O n the day of trial, but before the j ury wa s em pane le d, the Appe llant f

ile d anot ic e pur suant t o § 8 51( a) of it s in te nt t o r el y

on W il li am s’ pri orfel on y

dru g c on vi ct io ns to see k e nh an cedpu ni sh m en t. On Fe br uary 1, 200 5, the j ur

y f ound W ill iam s gu ilty

of a ll thr ee c ount s inthe indictm ent, m aking sp ecific finding s of the drug quant ities invo lved in each tr an sa ct ion . A t the se nte nc ing he ar ing , the dis tr ic t c ourt a dopt ed , w ith out obj ec tio n, the fa ct s and Guid el ine s c al cu la tio n se t ou t i n W ill iam s’ pr es en te nc e inv es tig at ion r e p o rt( P S I ) . Ac c o r d i n g t o th e P S I , Wi l l i a ms h a s ane x t e n s i v e c r i mi n a l h i s t o ry, w hic h be gan in199 1, w he n he w as six te eny ears old . His score d crim inal histo ryAll refe renc es to the Sentenc ing Guidelines ref er to the Guidelines eff

ective 2 November

1, 2004. 4 includes five convi ctions for poss ession o f cr ack cocaine ( two of which wer e co m m itt ed w iththe int en t t o se ll) , f

our c onvi ct ion s f

or of fe nse s in vol vin g poss ession o f m arij uana, one conviction for poss ession with int ent to sell MDMA (a c ontro lle d su

bst an ce a lso kno w n a s E cs ta sy ), and tw o c onvi ct ion s f or ba tte ry of tw o w om en , one of

w hom w as pr eg nant at the ti m e. A s ar es ult , W ill iam s ha d a tot al of 22 c ri m ina l hi sto ry

poi nts , w el l a

bove the 13 p oin ts n ee de d to pla ce him in th e h ig he stcri m in al hi st ory cat eg ory , cat eg ory

VI. The PSI ca lc ul at edW il li am s’ bas e o ffen se lev el at 2 8, p ur su an t t o U.S.S.G. § 2D1.1(c )(6). W illiam s’ m ultip le prior fe lonyconviction s for drug offenses 2 qualified him

as a c aree r offe nder under § 4B1.1(a). Bec ause the statutory m ax im um forhi s o ffen se s was li fe i m pr is on m en t, see 21 U. S. C. § 841 (b)(1)( B), § 4 B1 .1 en ha nc edW il li am s’ off en se lev el to 37 , see U.S.S.G. § 4 B1 .1(b )(A). W illiam s’ advisory

Guidelines range w as, ther efore, 360 m onth s to life im pr is on m en t. T he dis tr ic t c ourt se nte nc ed W ill iam s to 204 m onths’ inc ar ce ratio n ona ll counts, to run concurrently . The district court explained its choice of sentence at th e se nt en ci ng he ari ng an d i n i ts subs eque nt“ Mem or an du m Sen te nc in g Op in io n,”5

w hic h is pub lis he d a t Uni te d S ta te s v. Will ia ms , 372 F. Supp. 2d 1335 (M. D. Fla. 2005 ). I n e xpl ai nin g th e se nte nc e, the dis tr ic t c ourt purp orte d to tr ac k th e se nt en ci ng fact or s o ut li ne d i n 1 8 U.S.C. § 35 53 (a). A t the se nte nc ing he ar ing , the dis tr ic t c ourt e xpr es se d “ co nc er n a bout the discrepancy

betwee n powder and cra ck cocaine”—r efer ring to Cong ress’ s policy of pun ish ing c ra ck

c oc ai ne of

fe nde rs m or e se ve re ly

than po w de r co ca ine offenders—and viewe d the cocaine sentencing dis parity as bearing on “ the nature and circum stances of the offense. ” Se e id. § 355 3(a)( 1). The district court sugg es te d th e hars he r pe na lti es f or c ra ck of fe nse s “ sm ac ks o f dis cr im inatio n against blacks, Af

rican-A m ericans.” I t said crack c ocaine and powder coca ine are

“ the sam e drug” w ith the sam e ef fects and that the differ ent form of the drug “ has never j ustified the sub stantial dis parity in sentences.” The c ourt also cond em ned the DE A’ s conduct in investig ating W illiam s, char acter izing the stin g operation as

“ basically set up by the Governm ent to snare Mr. W illiam s.” The district court state d, w ith out

e la bor at ion , that this w as a lso r el ev an t t o “ the na tur e an d ci rcu m st an ces of t he off

en se .” In considering “ the seriousness of the offe nse” and the need for the sentence

“ to provid e j ust pu nishm ent,” se e id. § 355 3(a)( 2)(A ), the district court disagreed w ithw ha t i t c al le d th e “ co m poun din g e ff

ec ts” of the G uid el ine s, w hic h it

sa id6

ca use s “ inc ongr

uity and unj ust

r es ult s. ” T he dis tr ic t c ourt w as r ef er ri ng t o th e int er play be tw ee n th e G uid el ine s c ar ee r of fe nde r enhanc em en t, U . S. S. G . § 4B 1. 1, an d th e enhanc ed

statut or y m ax im um pr ovi de d in21 U . S. C. § 84 1( b) (1 )( B) f or of fe nde rs w itha t l ea st o ne pr ior f el ony dr ug c onvi ct ion . T he e nhanc ed of fe nse levels set out in § 4B1.1(b) f or car eer offenders vary

depending on the statuto ry m ax im um forth e o ffen se of c on vi ct io n. See U . S. S. G . § 4B 1. 1( b) . B ec au se W ill iam s ha d apr ior

c onvi ct ionf

or af el ony dr ug o ff en se , his statut or

y m ax im um sentence under § 841(b)(1)(B) increased fr om 40 y ears’ im

prisonm ent to life im pr is on m en t. See 21 U . S. C. § 84 1( b) (1 )( B) . T he § 84 1( b) (1 )( B) “ enhanc em en t” ha d th e co rr es pond ing e ff ec t un de r § 4B 1. 1( b) of

inc re as ing W ill iam s’ of

fe nse level from

28 to 37 . The district court sawthe interaction betwee n § 841 (b)(1)( B) an d § 4 B1 . 1( b) a s a“ tot al ly ina ppr opr ia te w ay

to co nsi de r the ind ivi dua l natur e of anof fe nse or ade fe ndant’ s in div idu al ba ck gr ound ” an d st at ed it w as “ not goi ng t o do it .” W ith respect to the “ histo ry and charac teristics of the defendant,” se e id. § 35 53( a) (1 ), the dis tr ic t c ourt no te d W ill iam s’ “ lon g hi sto ry of c ri m ina l c ondu ct ” an d st at ed

W ill iam s w as , the re fo re , “ goi ng t o be spe ndi ng a bun chof ti m e in prison.” T urning to the need for the sentence “ to afford adequate deter rence, ” see7

id. § 35 53( a) (2 )( B) , the dis tr ic t c ourt op ine d th at se ndi ng a

“pe tty dr ug d ea le r” li ke W illiam s to prison for 30 y ears w as not the way to deter the illegal drug trade. In its subs equent “ Mem orandum Sentencing Opinion,” the district court again addressed the cocaine sentencing disp arity . The district court stated it w as

“ m indful of the sub stantial criticism ” the disparity had garnered and that evid ence sugg es te d th e dis pari ty

ha d a“ dis cr im inator

y im pa ct on A fr ic anA m er ic an s of whom W illiam s is one.” W

il li ams , 372 F. Supp. 2d at 1339 n .8. T he district court’ s disd ain for the disparity fac tored into its choice of sentence in another w ay as w el l. E ch oin g it s e ar lie r state m en t tha t the D E Aha d sn ar ed W ill iam s, the dis tr ic t c ourt c onc lud ed

aG uid el ine s se nte nc e w oul d no t “pr om ote r es pe ct f or the law, ” se e id. § 355 3(a)( 2)(A ), because the D EAarr anged a sting p urchase of cr ack co cai ne in st eadof p owd er co cai ne to ob ta in a lo ng er p ris on sen te nc e. W il li ams , 372 F. Supp. 2d at 1339. W ithou t refe rring to any fac ts in the record, the district co urt f ound that a pow de r co ca ine sa le w oul d have be enc onsi ste nt w ithW ill iam s’ pr io r drug sal es . Id

. To h i g h l i g h tth e i n

ju s t i ce i tp er ce i v edi nth e G o v ern m en t ’s decision to purchase cra ck cocaine fr om W illiam s, the district court com pared W ill iam s’ G uid el ine s r an ge w iththe r an ge appl ic ab le to de fe ndants w ho, tho ughThe a dvisory Guidelines ra

ng e for a def endant c onvicted of se lling 34.8 grams of pow der 3 coca ine with a cr iminal hist ory cate g ory of VI is 37 to 46 mont hs’ imprisonment. SeeU.S.S.G. § 2 D1 .1 (c )( 13 ); c h. 5, pt. A. No ta bly , th e dis tr ic t c ourt

did no t c omp are Willi ams’ se nte nc e to the ra ng e applica

ble to a ca

ree r off ender convicted of

selling 34.8 grams of pow der c ocaine : 262 to 327 months’ imprisonm ent. See21 U.S.C. § 841(b)(1)( C); U.S.S.G. § 4B1.1(b); c h. 5, pt. A. 8 not c ar ee r of fe nde rs , have ac ri m ina l hi sto ry c at eg or y of V I an d are c onvi ct ed

of selling th e sam e quantity

of powder c ocaine. Id

. 3 T he dis tr ic t c ourt the n e xpl ai ne d, a s it did a t the se nte nc ing he ar ing , that a G uid el ine s se nte nc e w as ina ppr opr ia te f

or anothe r re as on, nam el y

it s di sa gr ee m en t wit h t he care er o ffen de r pr ov is io n i n § 4B 1.1 . Id . A cc or din g to the dis tr ic t c ourt, W il li am s’ pas t cr im in al co nd uc t was alr ead y acco un te d fo r in hi s ca te go ry VI cri m in al hi st ory . Id

. The “ lay ering of Chapter 4 enhancem ents,” the district court re as one d, “ re sul ts i n adouble -c om poun din g e ff

ec t, inc re as ing W ill iam s’ m ini m um guid eline sentence . . . in light of the same crim inal condu ct.” Id . T he district court stated this “ arbitrar y com poun ding results in a guidelin e sentence m uch gr eate r than th at

ne ce ssary ” to a ch ie ve the se nte nc ing goa ls e num er at ed in § 3 55 3( a). Id

. Finally , the district court explained that althoug h “ W illiam s is a low-level dr ug d ea le r . . . c onvi ct ed

of se lli ng r el at ive ly

sm al l am ount s of

c ra ck c oc ai ne , ” the

“ subs tanti al te rm ” of

204 m onths’ inc ar ce ratio n w as w ar rante d by “ the ci rc um stanc es ( cr ac k ve rs us p ow de r co ca ine ) an d W ill iam s’ lon g hi sto ry of se lli ng9

illegal drugs.” Id

. T he Appellant subsequ ently appealed W illiam s’ sentence as unreasonable. II. ST AN DA RD OF RE VIEW Our r eview of

sentences after United States v. B ooker , 543 U. S. 220, 125 S. Ct. 738 (200 5), has tw o com ponent s. F irst, w e consider challenges to the dist rict co urt’ s c al cu la tio n of

the a dvi sor

y G uid el ine s r an ge . S ec ond, w e re vie wthe se nt en ce fo r rea so nabl en es s. Se e Uni te d S ta te s v. Will ia ms , 435 F . 3d 1 350, 135 3 (1 1thCi r. 200 6) ( de te rm ini ng whe the r the dis tr ic t c ourt c or re ct ly c al cu la te d th e Guidelines range before evaluating the reasonableness of the sentence). A. G uid el ines C alc ula tio n

“ [A ] s was the c ase before Booker , the dis tr ic t c ourt m ust c al cu la te the Guidelines range acc urately .” U nited Sta tes v . Craw

for d , 407 F . 3d 1 174, 117 9 (1 1thCi r. 200 5) . W e re vie wthe dis tr ic t c ourt’ s in te rp re ta tio n of the G uid el ine s de no vo an d a ccep t i ts factua l fi nd in gs un le ss cle arl y erro ne ou s. United States v. Jo rdi , 4 1 8 F. 3 d1 2 1 2 , 1 2 1 4 (1 1 th Ci r. 2 0 0 5 ). An erro r i nth e d i s tri ct co u rt ’s ca lc ulatio n of

the a dvi sor

y G uid el ine s r an ge w ar

rants va catin g th e se nte nc e, unl es s th e err oris ha rm le ss . Se e U nited Sta tes v . Sc ott , 441 F. 3d 13 22, 1329 (11t h Cir. 20 06 ) (ap pl y in g h arm le ss erro r rev ie w to Gui de li ne s m is cal cu la ti on ). AThe § 3553(a ) sentenc ing f actor s include the nature a nd circ umstances of

the offe nse and 4 the history

and cha rac teristics of the de fenda nt; the need f

or the sente nce to r efle ct the seriousness of the offe nse, promote r espec t for the law , and provide just punishm ent for the offe nse; the nee d to deter c rime, protec t the public, and provide the def endant with educ ational or vocational tra ining, or

medical c are ; the kinds of sentenc es ava ilable; the SentencingGuidelines rang e; per

tinent policy

statements of the Sente ncingCommi ssion; the need to avoid unwa rra nted sentenc ing dispa

rities; and the nee d to provide re stitut ion to victims . 18 U.S.C. § 3553(a); United States v. W

iningear , 422 F.3d 1241, 1246 ( 11th Cir. 2005). 10 G uid el ine s m isc al cu la tio n is harm le ss i f the dis tr ic t c ourt w oul d have im pose d th e sa m e se nt en ce wi th ou t t he erro r. Se e id. B. R ea sona ble ness If the G uid el ine s c al cu la tio n is c or re ct , or if the m isc al cu la tio n is harm le ss, w e co nsi de r w he the r the se nte nc e is r ea sona ble . Whe n r ev ie w ing ase nte nc e fo r re as ona ble ne ss, w e m

ust e va luate w he the r the se nte nc e ac hie ve s th e pur pose s of sentencing as stated in 18 U. S. C. § 355 3(a). United States v. T alley , 431 F . 3d 4 78 4, 7 88 (11 th Cir . 20 05 ). Thi s ev al ua ti on m us t b e m ad e h av in g “ reg ardfor. . . the f ac tor s to be c onsi de re d inim posi ng a se nte nc e, a s se t f

orth i n [ § 35 53( a) ] ; and

. . . the r ea sons f

or the im posi tio n of

the part ic ular se nte nc e, a s st at ed by the district court pursu ant to the provis ions o f section 3553 (c). ” Booker , 543 U. S. at 261, 125 S . Ct . a t 76 5 ( quot ing 18 U . S. C. § 37 42( e) (3 ) (1 994) ); se e als o W il li ams , 435 F. 3d at 13 55 ( statin g th at “ w he n r ev ie w ing f

or r ea sona ble ne ss, w e m

ust co ns id er b ot h t he § 3 55 3( a) fa ct or s an d t he reas on s g iv en by the di st ric t co ur t” ).We rea liz e a se ntence could be a lleg ed to be unr easona ble on g rounds other tha

n leng th. 5 Her e, the Gove rnment conte sts only the leng th of Wil liams’ sentenc e, so we confine our discussion to length. Our opinion should notbe re ad to fore close other possible challeng es to the rea sonablene ss of the terms of a sentenc e. 11 T he party c ha lle ngi ng the se nte nc e be ar s th e bur de n of e sta bli shi ng the se nte nc e is un reas on ab le in li gh t o f th e § 35 53 (a) fa ct or s. Talley , 431 F . 3d at 78 8. Inor de r to t ai lor

our r ea sona ble ne ss s tandard

of r ev ie wto the iss ue s inthi s ca se , w e m

ust f ir st i de nti fy

the c ha lle nge s A

ppe llant m ak es to the r ea sona ble ne ss of W illiam s’ sentence. First, Appellant argues the sentence is unreasonable, re gard le ss o f le ngth, be ca use it r es ult ed f ro m the dis tr ic t c ourt’ s c onsi de ratio n of im pe rm iss ibl e fa ct or s. S ec ond, Appe llant c ont en ds i n th e al te rn at ive that, e ve n if W ill iam s’ se nte nc e w as not a ff ec te d by le ga l e rr or s, the le ngth of the se nte nc e is unreasonable because the rec ord does no t supp ort a deviation from the Guidelines range. 1. Re ason s for th e Sentence W ithr es pe ct

to Appe llant’ s f

ir st arg um en t, w e ag re e that a se nte nc e can be unreasonable, re gardless of length, if the district court’ s selection of the sentence 5 w as sub stanti al ly

a ff ec te d by it s c onsi de ratio n of

im pe rm iss ibl e fa ct or s. T his is so, because our rea sonablen ess inqu iry is not confin ed to review ing whether there are fa ct s and c ir cum stanc es f ound in the r ec or d th at

w oul d j ust if

y the le ngth of

the12

se nt en ce i m

po se d. Se e U

nited Sta tes v . W

eb b , 403 F . 3d 3 73, 383 ( 6thCi r. 200 5) (“ [R]evi ew fo r rea so nabl en es s i s n otli m it edto th e le ng th of t he sen te nc e.” (quotation om itted)). T he rea sons given bythe district court for its selection of a se nt en ce ar e im

po rta ntto ass es si ng reas on ab le ne ss . U nited Sta tes v . J

im en ez B el tre , 440 F . 3d 5 14, 519 ( 1st Ci r. 200 6) ( enbanc ) (s ta tin g th e em pha sis in review ing th e re asonableness o f a sentence “ will be on the provisio n of a re asoned e x p l an a t i o n , ap l au s i b l e o u t c o me an d

—w h e r e th e s e c r i t e r i aar e me t

— s o me defere nce to differ ent j udgm ents by the district judges on the scene”). Asentence ba se d onan im

pr ope r fa ct or

f ai ls t o a ch ie ve the pur

pose s of § 35 53( a) and m ay

be un reas on ab le , reg ard le ss of l en gt h. U nited Sta tes v . M

ore lan d , 437 F . 3d 4 24, 434 (4th Cir. 2006 ) (“ A sentence m ay be substant ively

unreasonable if the court relies on an im pr ope r fa ct or

or r ej ec ts p oli ci es art ic ulate d by Co ngr es s or

the S en te nc ing Com m issio n.”) . Be ca use the party

c ha lle ngi ng the se nte nc e be ar s th e bur de n of dem onstrating that the sentence is unreasonable, the party challenging th e sentence bears the initial burden of establish ing th at the district court considered an im pe rm iss ibl e fa ct or

a t se nte nc ing . Whe the r a fa ct or is im pe rm iss ibl e is a qu es ti on of l aw th atwe wil l re vi ew de no vo . Se e U nited Sta tes v . R obi nson , 935 F. 2d 2 01, 203 ( 11th C ir . 199 1) ( “ T he appl ic at ionof the lawto se nte nc ing iss ue s is13

subj ec t t o de nov o r ev ie w . ”) . I f suc h an e rr or e xis ts and w as pr es er

ve d f or appe al , we wil l v acat e th e se nt en ce an d re m an d, u nl es s t he erro r is ha rm le ss . See 28 U . S. C. § 21 11; F ed . R. Cr im . P . 52( a) . T he party de fe ndi ng the se nte nc e ha s th e bu rd en of e st ab li sh in g t he erro r was ha rm le ss . Se e, e . g. , United States v. M ath en ia , 409 F. 3d 12 89, 1291-92 (11th Cir. 2005). In considering whether an er ror is harm less, w e apply our traditional harm le ss e rr or

standard : “ A‘ non- co nst itutio na l e rr or is harm le ss i f, vie w ing the pr oc ee din gs i n th ei r en tir ety , ac ourt de te rm ine s th at the e rr or did not a ff ec t the se nt en ce, ‘or h adbu t v ery sl ig hteffe ct .’ If on e can say ‘ wit h fa ir a ss ur an ce . . . that the se nte nc e w as not sub stanti al ly

sw ay ed by the e rr or , ’ the se nte nc e is d ue to be aff irm ed even thoug h there w as err or.” Id. at 129 2 ( quot ing United States v. H orna day , 392 F . 3d 1 306, 131 5- 16 ( 11th C ir . 200 4) ( quot ing Kotteakos v. U nited States , 328 U . S. 750 , 762 , 763 , 66 S . Ct . 123 9, 124 6, 124 8 ( 1946 )) ); se e als o Uni te d S ta te s v. Will ia ms , 503 U . S. 193 , 203 , 112 S . Ct . 111 2, 112 0- 21 ( 1992 ) (holdin g that once the party challenging th e sentence shows the district court re lie d onan in va lid

f ac tor a t se nte nc ing , “ a re m an d is appr opr ia te unl es s th e re vie w ing c ourt c onc lud es , on the r ec or d a s aw hol e, that the e rr or w as harm le ss, i.e. , that the e rror did not affec t the district court’ s selection of the sentence im pose d” ); United States v. Paley , 442 F . 3d 1 273, 127 8 ( 11th C ir . 200 6) ( statin g a14

district court’ s m isinterpretation of the Guidelines is harm less if the district court w oul d have im

pose d th e sam e se nte nc e ab se nt the e rr or ); United States v. J ones , 1 F. 3d 11 67, 1171 (11t h Cir. 1993 ) (“ A sentencing err or is harm less if the rec ord as a w hol e show s th at

the e rr or did not a ff ec t the dis tr ic t c ourt’ s se le ct ionof the se nte nc e im

pose d. ”) . C onsi ste nt w iththi s st an dard , adis tr ic t c ourt’ s c onsi de ratio n of an im pe rm is si bl e fac to r atsen te nc in g i s h arm le ss if t he reco rdas awho le sh ows the error did no t subs tantially

aff ect the district court’ s selection of the sentence im po se d. If the e rr or is not harm le ss, w e w ill go n o f urthe r, and w ill va cate the se nte nc e an d r em an d f

or the dis tr ic t c ourt t o im

pose ase nte nc e ba se d onthe ind ivi dua liz ed

f ac ts and c ir cum stanc es of the de fe ndant’ s c as e be ar ing upo n th e se nte nc ing c onsi de ratio ns e num er at ed in § 35 53( a) . I f, on the oth er hand, the party de fe ndi ng the se nte nc e is s uc ce ssf ul i n sh ow ing the e rr or

did not subs tantially

aff ect the district court’ s selection of the sentence, w e m ust then re sol ve w he the r the se nte nc e is r ea sona ble in lig ht o f the § 35 53( a) f ac tor s and the re as ons giv enby

the dis tr ic t c ourt. Insum , to suc ce ed

on a c la im that an im

pe rm iss ibl e fa ct or

a ff ec te d th e se nte nc e, the party

c ha lle ngi ng the se nte nc e ha s th e ini tia l burd enof e sta bli shi ng that the dis tr ic t c ourt c onsi de re d an im pe rm iss ibl e fa ct or

in fa shi oni ng the15

sentence. If we conclude after a de novo review that the district court considered an im perm issib le fac tor at sentencing, and if the er ror w as preserved, the burden shifts to th e party

defending the sentence to sho w, based on the record as a whole, th atth e err oris ha rm le ss , i.e. , t h at th e e rr o r d i dn o ts ub s t an t i al l y af fe ct th e c o u rt ’s choice of sentence. If

the err or is not harm less, w e w ill vacate the sentence a s unreasonable and rem and for the district court to resentence the def endant based on the ind ivi dua liz ed

f ac ts and c ir cum stanc es of the de fe ndant’ s c as e be ar ing upo n the se nte nc ing c onsi de ratio ns e num er at ed in § 35 53( a) . I f the e rr or is harm le ss, we will re view the sentence f or rea sonablen ess in ligh t of the § 3553 (a) factors an d th e re as ons giv enby

the dis tr ic t c ourt. 2. Unreasonab le Length of the Sentence Appe llant arg ue s th at

e ve n if the dis tr ic t c ourt c onsi de re d on ly pe rm iss ibl e se nte nc ing f

ac tor s, the le ngth of

W ill iam s’ se nte nc e is unr ea sona ble be ca use the fa ct s and c ir cum stanc es of W ill iam s’ c as e do n ot w ar rant any de viatio n f

ro m the advis or y G uid el ine s r an ge . I n e sse nc e, Appe llant c ont en ds tha t, a ssum ing the se nte nc e is b as ed

on o nly pe rm iss ibl e fa ct or s, the dis tr ic t c ourt ne ve rthe le ss m ad e a clear er ror of j udgm ent in weighing th ose factors in W illiam s’ case. W e re vie wthe le ngth of

ase nte nc e fo r re as ona

ble ne ss i n li ght

of the f ac ts an d c ir cum stanc es of

the de fe ndant’ s c as e re fl ec tin g th e se nte nc ing c onsi de ratio ns16

in § 3 55 3( a). Talley , 431 F. 3d at 788 . “ Reviewfor r easonableness is deferential.” Id . A nd w e m

ust be ar in m ind “ that the re is a range of

r ea sona ble se nte nc es f

ro m which the district court m ay choose.” Id

. T he we ight to be acc orded any given § 3 55 3( a) fa ct or

is a m at te r co m

m it te d t o t he so un d d is cret io n o f th e d is tri ctco ur t. See U nited Sta tes v. Fe rnan dez , 443 F . 3d 1 9, 32 ( 2d C ir . 200 6) . W e w ill not subs tit ute our j udgm en t i n w ei ghi ng the r el ev an t f ac tor s be ca

use “ [o ] ur

r ev ie wis not de no vo.” Talley , 43 1 F .3dat 7 88 . The district court’ s choice of sentence, however, is not un fettere d. When re vie w ing the le ngth of

ase nte nc e fo r re as ona

ble ne ss, w e w ill r em an d f or resentencing if w e ar e left w ith the definite and firm conviction that the district co urt c om

m itt ed ac le ar e rr or of j udgm en t i n w ei ghi ng the § 35 53( a) f ac tor s by arriving at a sentence that lies outside the range of re asonable sentences dictated by the fact s o f th e cas e. See U nited Sta tes v . M

art in , __ F . 3d _

_, N o. 05- 1664 5, 2006 W L 1889902 , at *10-13 (11th Cir. July 11, 2006) (concludin g a seven-day se nte nc e fo r a m

ult i- bil lio n- dol lar se curi tie s f ra ud w as unr ea sona

ble ); United Sta tes v . Cr isp , __ F. 3d __ , N o. 05-12304 , 2006 W L 1867754 , at *6 (11th Cir. J u l y 7 , 2 0 0 6 ) ( v ac at i n g a s en t en ce as u n re as o n ab l e b ec au s e o f t h e d i s tri ct co u rt ’s unjustified reliance on a singl e § 3553(a) fac tor to the detrim ent of the others); M ore lan d , 437 F . 3d at 43 6 ( co nc lud ing the dis tr ic t c ourt c om m itt ed “ ‘ a cl ear er

ro r17

of j udgm ent by

arr iving at a sentence outsi de the lim ited range of choice dictated by the f ac ts o f the c as e’ ”) ( quot ing U nited Sta tes v . H

aw k W ing , 433 F . 3d 6 22, 631 (8 th C ir . 200 6) ); U

nited Sta tes v . Sm ith , 440 F . 3d 7 04, 708 ( 5thCi r. 200 6) (h old ing anon -Guid el ine s se nte nc e m ay be unr ea sona

ble w he re it

“ re pr es en ts a cl ear er ro r of j udgm en t i n ba lanc ing the se nte nc ing f ac tor s” ); United States v. Se bast ian , 436 F . 3d 9 13, 915 ( 8thCi r. 200 6) ( hol din g ase nte nc e m ay be unr ea sona

ble if the dis tr ic t c ourt “ co m

m its ac le ar

e rr or in j udgm en t i n w ei ghi ng the sentencing factors”). III. D ISCU SSION A. G uid el ines C alc ula tio n The f irst step in ou r re view is to determ ine whether the district court pr ope rl y int er pr et ed and a ppl ie d th e G uid el ine s to W ill iam s’ c as e to arr ive a t a co rrec t ca lc ul at io n o f W il li am s’ adv is ory Gui de li ne s ra ng e. Se e W il li ams , 435 F.3 d a t 1 35 3. Th ere i s n o d is pu te ab ou t t he di st ric t co ur t’s Gu id el in es cal cu la ti on . T he dis tr ic t c ourt a cc ur at el y c al cu la te d W ill iam s’ a dvi sor y G uid el ine s r an ge usi ng an enhanced offense level of 37 and crim inal histo ry category of V I, corresponding to an advisory Guidelines range of 360 m onth s to life im pr iso nm en t. Mo re ove r, the dis tr ic t c ourt e xpr es sly c onsi de re d th e pr ope rl y cal cu la te d Gu id el in es ran ge in im po si ng a no n- Gui de li ne s s en te nc e.18

B. R ea sona ble ness 1. Re ason s for th e Sentence Appe llant arg ue s th e dis tr ic t c ourt c om m itt ed m ult ipl e le ga l e rr or s in ap ply ing the § 35 53( a) f

ac tor s to W ill iam s’ c as e. S pe ci fi ca lly , Appe llant c ont en ds the dis tr ic t c ourt e rr ed

in thr ee w ay s: (1 ) it re

j ec te d C ongr es s’ s po lic y

of puni shi ng c ra ck

c oc ai ne of

fe nde rs m or e se ve re ly

than po w de r co ca ine of

fe nde rs ; (2 ) it re fu se d to se nte nc e W ill iam s a s ac ar ee r of fe nde r, the re by

r ej ec tin g Co ngr es s’ s po lic y

of pun ish ing r ec idi vis t dr

ug o ff en de rs m or e se ve re ly ; and ( 3) it er ro ne ousl y c onc lud ed

the G ove rn m en t e nga ge d inse nte nc ing m an ipu la tio n by ar rangi ng t o purc ha se c ra ck c oc ai ne ins te ad

of pow de r co ca ine and e rr ed in fa ct or ing thi s c onc lus ionint o W ill iam s’ se nte nc e. A cc or din g to Appe llant, the se im perm issib le considerations affected the district court’ s choice of sentence, re nde ri ng the se nte nc e unr ea sona ble , r eg ar dle ss o f le ngth. B ec au se the se co nte nti ons pr es en t qu es tio ns o f lawa s to the pr ope r co nsi de ratio ns at se nte nc ing , w e w ill r ev ie wde nov o w he the r the dis tr ic t c ourt c onsi de re d im pr ope r fa ct or s in fashionin g W illiam s’ sentence.Se c tio n 8 41 re fe rs to “ c oc a ine ba se ,” and the Se nte nc ingGu ide lin e s d e fi ne c oc a ine ba se 6 to mean cr ack c ocaine . See U.S.S.G § 2D1.1(c), n.D . Simi larly , § 841(b)( 1)(A) sets the sentenc ing r ang e for offe nses involving 50 grams or 7 m o r e o f c r a c k c o c a i n e o r

5 k i l o g r am s o r

m o r e o f p o w d e r c o c a i n e att e ny e ar s t o l i f e i np r i s o n . If the def endant ha s at least one prior conviction for a fe lony drugoffe nse, § 841(b) (1)( A) re quires a sente nce be tween 20 year s and life in prison. 19 a. Im permissible Consideration s Affec ting th e Sentence i. Th e Co ca ine Se nte nc ing D isp ari ty Und er 2 1 U.S.C. § 84 1 a nd§ 2 D1.1 of t he Sen te nc in g Gu id el in es , a defendant convicted of an offense involv ing “ cocaine base” ( i.e. , c rack c ocaine) 6 fa ce s alon ge r poss ibl e se nte nc e than ade fe ndant c onvi ct ed of an of fe nse in vo lv in g t he same am ou ntof p owd er co cai ne , a ch em ic al ly-si m il ar s ub st an ce. T his dis pari ty

is co m m onl y r ef er re d to a s th e “ 100- to- 1” r at io, so n am ed be ca use of the r el at ive quanti tie s of e ac h dr ug r equir ed

to tr igg er the m an da tor

y se nte nc ing range s in§ 84 1( b) . F or

e xam ple , § 84 1( b) (1 )( B) pr ovi de s th at of fe nse s in vol vin g 5 gr am s or

m or e of c ra ck c oc ai ne or

500 gr am s or

m or e of pow de r co ca ine c al l f

or sentences in the range of 5 to 40 y ears’ im prisonm ent. W

here the def

endant has at le as t on e pr ior

c onvi ct ionf

or af el ony dr ug o ff en se , § 84 1( b) (1 )( B) e nhanc es the sentencing range to ten y ears to life in prison . Congress enacted harsher penalties 7 for cr ack cocaine than for powder coca ine based on its conclusion that crac k cocaine poses a greate r threat to society . Specifica lly , C ongress foun d crac k20

cocaine (1) has a m ore ra pid on set of action, ( 2) is m ore potent, (3) is m ore addictive, (4) is less expensive than powder cocaine, (5) has w idespread availability , ( 6) m ore highlycorre lates with the incidence of violence and other cr im es , ( 7) is m or e lik el y to have phy sio log ic al e ff ec ts, and ( 8) is m or e lik el y to at tra ctus ers who are youn g o r es pe ci al ly vul ne rab le . See U nited Sta tes v . B

ys e , 28 F. 3d 1 165, 116 9 ( 11th C ir . 199 4) ( quot ing U nited Sta tes v . T

hurm ond , 7 F . 3d 9 47, 953 (1 0thCi r. 199 3) ); U . S. S en te nc ing Co m m ’ n, S pe ci al Re port t o th e Co ngr es s: Co ca ine and F ed er al S en te nc ing P oli cy 118 ( 1995 ). T he S en te nc ing Co m m iss ion ad opt ed the sam e 100- to- 1 c ra ck -t o- pow de r co ca ine r at io i n e sta bli shi ng the D ru g Q uanti ty T ab le in U . S. S. G . § 2D 1. 1( c) , w hic h se ts the of fe nse le ve ls f

or dr ug offenses. For exam

ple, § 2D 1.1(c) (6) designates offense level 28 for off enses invo lving 20 to 35 gram s of cra ck cocaine or 2 to 3.5 kilogram s of powder cocaine. In199 4, Co ngr es s di re ct ed the S en te nc ing Co m

m iss ionto co nduc t a

stu dy of the dis pari tie s inpe na lti es f or dif fe re nt f orm s of c oc ai ne and t o m ak e reco m m en da ti on s ab ou t re ta in in g o r m od ifyin g t he di sp ari ti es . See V i o l e n tC r i me Co ntr ol and L aw

E nf or ce m en t A ct

of 199 4, P ub. L . N o. 103 -3 22, § 28 0006 , 108 St at . 179 6, 209 7 ( 1994 ). P ur suant t o th is d ir ec tiv e, the Co m m iss ioniss ue d a report to Congress in 19 95 in which it agreed w ith Cong ress’ s finding that “ crac kTh e Se nte nc ingCommis sio n’ s r e po rt s a re ava ila ble at http: //www .u ssc .g ov/r e po rt s. htm . 8 21 cocaine poses greater harm s to society than does po wder

cocaine, ” but concluded

“ it [could not ] rec omm end a ratio differ ential as great a s the current 100-to-1 quanti ty r at io. ” U . S. S en te nc ing Co m m ’ n, S pe ci al Re port t o th e Co ngr es s: Co ca ine and F ed er al S en te nc ing P oli cy 195 -9 6 ( 1995 ). O ne r ea son w hy the 8 Co m m iss ionr ej ec te d th e 100- to- 1 r at io w as that C ongr es s a dopt ed it pr ior to the G uid el ine s takin g e ff

ec t, and the Co m

m iss ionbe lie ve d th at

m any , but

not a ll, of the a tte ndant a ddi tio na l harm s of c ra ck vis -à -v is p ow de r co ca ine ( suc h a s th e in crea se in vi ol en t an d o th er cr im es ) are n ow ac co un te d fo r in th e Gui de li ne s. Id . at 196 (“ [I] f Congress believed that certain fa ctors warranted a 100-to-1 quanti ty r at io and i f the sub se que ntl y a dopt ed gui de lin es pr ovi de d apun ish m en t fo r som e of

tho se f ac tor s, the n, a s alog ic al m atte r, the r at io s houl d be low er ed by ana m ount

c om m en sur at e w iththe e xte nt t o w hic h th es e fa ct or s are a ddr es se d by th e g ui de li ne s.”) . T he Co m m iss ionsub se que ntl y

pr opos ed G uid el ine s am en dm en ts tha t w oul d el im in at e en ti rel y

th e se nt en ci ng di sp ari ty bet ween crac k a ndpo wde r co cai ne . See N oti ce of

S ubm iss ionto Co ngr es s of A m en dm en ts t o th e Se nte nc ing G uid el ine s, 60 F ed . Re g. 25, 074, 25, 076 (M ay 10, 199 5) . A lth oughCo ngr es s state d “ the c ur

re nt 1 00- to- 1 qu an tity

r at io m ay

not be the appr opr ia te r at io, ” it22

rej ected the Com

m issio n’ s propos als because “ the evidence clear ly indicates that the re are sig nif

ic ant di sti nc tio ns b etw ee n c ra ck and p ow de r co ca ine that w ar rant m ai nta ini ng l onge r se nte nc es f or c ra ck -r el at ed

of fe nse s” and “ gr oss se nte nc ing dis pari tie s” w oul d r es ult

if the pr opos al s w er e to t ak e ef fe ct w ith out Co ngr es s low er ing the statut or

y m an da tor

y m ini m um pe na lti es . H . R. Re p. N o. 104 -2 72, a t 4 (1 99 5) , re pri nte d in 199 5 U . S. C. C. A . N . 335 , 337 ; se e als o F ed er al S en te nc ing G uid el ine s, A m en dm en t, D isa ppr ova l, P ub. L . N o. 104 -3 8, § 1, 109 S ta t. 334 , 334 (1 99 5) . T he Co m m iss ioniss ue d ase co nd r ep ort i n 19 97, a ga in at the dir ec tio n of Co ngr es s. U . S. S en te nc ing Co m m ’ n, S pe ci al Re port t o th e Co ngr es s: C oc ai ne and Fe de ra l S en te nc ing P oli cy ( 1997 ). I n th is r ep ort, the Co m m iss ionr ei te rate d it s earlier finding th at “ althoug h resear ch and publ ic policy m ay suppo rt som ew hat hig he r pe na lti es f

or c ra ck than f or pow de r co ca ine , a100 -t o- 1 qu an tity r at io cannot be justified.” Id

. a t 2. T he Co m

m iss ionr ec om

m en de d th at

Co ngr es s a dj ust th e m an da to ry

sen te nc in g ra ng es to refl ecta 5- to -1 rat io . Id . Congress, howe ver, too k no a ct ion . In200 2, a t the r eque st o f the S en at e Judi ci ar y Co m m itt ee , the Co m

m iss ion iss ue d athi rd

r ep ort onthe c ra ck -t o- pow de r dis pari ty . U . S. S en te nc ing Co m m ’ n, Re port t o th e Co ngr es s: C oc ai ne and F ed er al S en te nc ing P oli cy ( 2002 ). I n th eFor example, the Commi ssion pointed to studies showingthe ef fec ts of prenatal cra ck 9 coca ine exposure wer e the same for pow der c ocaine and that the e pidemic of youngusers a nd distributors “never

materia liz ed to the extent fea red.” U.S. SentencingComm’n, Report to the Congr ess: Cocaine a

nd Fe dera l SentencingPolicy 93-97 (2002) . For example, the Commi ssion stated that althoug h studies showed har mful conduct 10 (s uc h a s v iol e nc e ) o c c ur s mo re of te n in c ra c k c oc a ine of

fe ns e s th an in

po wd e r c oc a ine of

fe ns e s, “it occur s in only

a re latively

small minority

of cr ack c ocaine offe nses.” U.S. Sentenc ing Comm’ n, Re po rt

to t he Con g re ss: Coc a ine and F e de ra l Se nte nc ingPol ic y 10 0 ( 20 02 ). Thus , “ to the e xtent th at th e 10 0- to- 1 d ru gratio wa s d e signe d to a c c ount f or the ha rm fu l c on du c t . . . , it swee ps too broadly

by treating a ll crac k coca ine offe nders a s if they committed these var ious harmful a cts, eve n though most cr ack c ocaine offe nders in fa ct had not.” Id. Although the Commi ssion recognized that “some diffe rential in the qua ntity -base d penalties for

cra ck coc aine and powde r coc aine is wa rra nted” be cause sentenc ing e nhance ments did not account for the fa ct that “tra ffickingin cra ck coc aine is assoc iated with somewhat gr eate r leve ls of sy stemic crime,” 23 re port, the Co m

m iss ion“ fi rm ly

and unanim ousl y ” de cl ar ed the 100 -t o- 1 dr

ug quanti ty r at io “ is unj ust if

ie d and f ai ls t o m ee t the se nte nc ing obj ec tiv es se t f orth by Congress.” Id

. a t 91 . T he Co m

m iss ionm ad e fo ur

pr inc ipa l f

ind ing s. F ir st, it found th at curre nt penalties exaggerate the relative harm fulness of crack c ocaine. 9 Id . a t 93 -9 7. A lth oughthe Co m m iss ionf ound that c ra ck

w as the m ost

a ddi ct ive form of cocaine bec ause of the m ethod of ing estion, it concluded th is difference al on e d idno t warran t t he 10 0- to -1 rat io . Id . a t 94 . S ec ond, the Co m m iss ion concluded th e curr ent penalties sweep too broadly and apply

m ost often to lo we rlevel offenders, cre ating dis parate penalties in com parison to si m ilar powder co cai ne off

en de rs an d o ve rs ta ti ng th e cu lp ab il it y of m os t cr ackco cai ne off en de rs . Id . a t 97 -1 00. T hir d, the Co m m iss ionf ound the pe na lti es ove rs ta te the se ri ousn es s o f mo s tc r a c kc o c a i n e o f

f e n s e s an df

a i l t o p r o v i d e a d e qu a t e p r o p o rt i o n a l i ty. 10it opined that this consideration did not justi fy the 100-to-1 r atio. Id. at 101-02. 24 Id . at 100-02. Fourth, the C omm issio n found th at the curre nt penalties im pact m in or it ie s m os t s ev erel y , fos te rin g d is res pe ctforth e cri m in al jus ti ce s y st em . Id . at 102 -0 3. B as ed

on the se f

ind ing s, the Co m

m iss ionr ec om

m en de d th at

Co ngr es s re vis e the m an da tor

y se nte nc ing r an ge f

or c ra ck and p ow de r co ca ine to im ple m en t a 20- to- 1 dr

ug quanti ty

r at io. I d. a t 10 7. T he Co m

m iss iona lso a ske d C ongr es s f or gui danc e in c hangi ng the G uid el ine s stru ct ur e to b ette r targ et

the m ost se ri ous drug off en de rs . Id

. at1 0 8 . Ag ai n , C o n g re s s d i dn o tac to nth e C o m m i s s i o n ’s reco m m en da ti on s. W iththi s ba ck gr ound

in m ind , w e tur

n to the dis tr ic t c ourt’ s tr eatm en t of the co ca ine se nte nc ing dis pari ty . T he dis tr ic t c ourt di sa ppr ove d of

the se ve ri ty

of Congress’ s disp arate treatm ent of cra ck cocaine off enders relative to powder co ca ine of

fe nde rs . A t se nte nc ing , the dis tr ic t c ourt e xpr es se d it s be lie f that the dis pari ty “ sm ac ks o f dis cr im inatio n” and tha t the dif fe re nc e be tw ee n c ra ck

c oc ai ne an d p owd er co cai ne “ ha s n ev er jus ti fie d t he subs ta nt ia l d is pa rit y in sen te nc es .” E ve n th oughthe dis tr ic t c ourt di d no t c om ple te ly r ej ec t C ongr es s’ s po lic y

of im posin g harsher penalties on crack off enders, it took into account it s personal dis ag re em en t w ithCo ngr es s’ s j udgm en t a s to howm uc h hars he r the pe na lti es f orSee also United States v . Miller , 4 50 F .3 d 2 70 , 2 75 (7 th C ir . 2 00 6) (a g re e ingwi th 11 Pho and Eu ra ). 25 crac k offenders shouldbe. To the e xtent the dis trict court did so, it considered an im perm issib le fac tor in fashionin g W illiam s’ sentence. T he F ir st C ir cu it’ s de ci sio n in U nited Sta tes v . Pho , 433 F.3d 53 (1st Cir. 2006 ), and the F ourth C ir cu it’ s de ci sio n in U nited Sta tes v . Eura , 440 F . 3d 6 25 (4th Cir. 2006 ), are particularly instructive. T he district courts in bo th cases

11 cate gor ic al ly

r ej ec te d th e 100- to- 1 dr

ug quanti ty

r at io b ec au se the y

be lie ve d it ove rs ta te d w ha t the pe na lti es oug ht t o be f or c ra ck c oc ai ne of

fe nde rs r el at ive to po wde r co cai ne off

en de rs . Pho , 433 F . 3d at 58 -5 9; Eura , 440 F. 3d at 631 -32. I n se nte nc ing the de fe ndants be lowthe a dvi sor y G uid el ine s r an ge , the dis tr ic t c ourts fa ile d to m en tio n any

f ac ts c onc er

nin g th e de fe ndants a s in div idu al s th at w oul d have warranted non-Guidelines sentences, but instead relied on the general in equi ti es th ey

pe rcei ve d e xi st edin th e 1 00 -to -1 rat io . Pho , 433 F . 3d at 64 ; Eura , 440 F. 3d at 63 4. T he F ir st and F ourth C ir cu its va cate d th e se nte nc es , c onc lud ing that di str ic t c ourts are bound b y Co ngr es s’ s po lic y

j udgm en ts c onc er

nin g th e ap pr op ria te pe na lt ie s fo r fed eral off en se s. Pho , 433 F . 3d at 62 -6 3; Eura , 440 F . 3d at 633-34. Both courts held th at sentences m ust be based on indiv idualized as pe ct s of the de fe ndant’ s c as e that f it w ith in the § 35 53( a) f

ac tor s, and n ot o nPos t- Booke r , w e have re je c te d a de fe nd ant’ s c ha lle ng e to t he re a so na

ble ne ss o f h is 12 sentenc e pre dicated on the disparity betwee n cra ck and pow der c ocaine . See U nited States v. Ma rli n , 147 F. App’ x 122, 124 (11th Cir. 2005) (unpublished opinion). 26 ge ne ral iz eddi sa gr eem en t wi th co ng res si on al sen te nc in g p ol ic y . Pho , 433 F. 3d at 64- 65; Eura , 440 F . 3d at 63 4. We a g re e w i th th e F i rs tan dFo u rt h Ci rc u i t ’s co n cl u s i o n s . C o n g re s s ’s de ci sio n to pun ishc ra ck

c oc ai ne of

fe nde rs m or e se ve re ly

than po w de r co ca ine offenders is plainly

a policy decision. It r eflec ts Congress’s j udgm ent that crac k co ca ine pos es agr eate r harm to soc ie ty

than po w de r co ca ine . W e have r ep eate dly h e l dC o n g r e s s ’s d i s p ar a t e tr e a t men to f c r a c k c o c a i n e o f

f e n d e r s i s s up p o rt e db y a rat io na l b as is . Se e, e . g. , B ys e , 28 F . 3d at 11 68- 71 ( re j ec tin g e qua l pr ote ct ion challenge that the crac k-to-powder coca ine disparity constitu tes intentio nal race dis cr im inatio n) ; U

nited Sta tes v . Slo an , 97 F . 3d 1 378, 138 3- 84 ( 11th C ir . 199 6) (holdin g the sentencing disparity is supp orted by

a rational basis ). T he 100-to-1 12 drug quan tity

ratio not onlyref

lects Congress’ s policydecision that crack of fe nde rs sho uld

be pun ish ed

m or e se ve re ly , but

a lso r ef le ct s it s c hoi ce a s to how m uc h m or e se ve re the pun ish m en t sh oul d be . F ed er al c ourts are not a t l ibe rty to supp la ntth is po li cy

de ci si on . Se e Pho , 433 F . 3d at 62 -6 3; Eura , 440 F . 3d at 63 3; see also Mistretta v. U

nited Sta tes , 488 U . S. 361 , 364 , 109 S . Ct . 647 , 650 -5 1 (1989) (“ Congress, of course, has the power to f ix the sentence for a f

ederal c rim e,27

an d th e sc ope of

j udi ci al dis cr et ionw ithr es pe ct to a se nte nc e is s ubj ec t t o congression al control.” ( internal citation om itted)). A lthou gh the two drugs m ay be c he m ic al ly

similar, the ir

e ff ec t onsoc ie ty

is not the sam e, and i t i s no t f

or the co urts t o say

j ust howm uc h w or se c ra ck

c oc ai ne is than po w de r co ca ine . T his is sim ply an im pe rm iss ibl e se nte nc ing c onsi de ratio n. A s th e Se ve nthCi rc uit aptl y put it: “ § 355 3(a) . . . does not include a factor such as ‘ the j udge thi nks th e law m isgui ded.’ ” Miller , 450 F . 3d at 27 5. W ill iam s, how ev er , a sse rt s th at the c ra ck ve rs us p ow de r co ca ine se nte nc ing dis pari ty is a va lid c onsi de ratio n un de r § 35 53( a) (6 ), w hic h r equir es c ourts t o co nsi de r “ the ne ed

to av oid unw ar rante d se nte nc e dis pari tie s am ong de fe ndants with sim ilar re cords who have been found guil ty of sim ilar conduct.” Severa l di st ric t co ur ts th atha ve ad dr es se d t he is su e ag ree wi th W il li am s’ po si ti on . See, e. g. , United States v. F

isher , __ F. Supp. 2d __, 2005 W L 2542916 , at *8-9 (S . D . N . Y . O ct . 11, 200 5) ; U nited Sta tes v . Sm ith , 35 9 F . Sup p. 2 d 7 71 , 78 1 (E.D. W is. 200 5) . P ow de r co ca ine of fe nde rs , how ev er , have not be enf ound gui lty of sim ilar conduct in any

relevant sense. Congress has determ ined that crack offenders and powder offenders ar e not sim ilarly situated, and that the disparities cau se d b y it s ch oi ce o f th e 1 00 -to -1 dru g q ua nt it y rat io are warran te d. Se e Pho , 433 F.3d at 64 (“ Congress plainl y believed that not all cocaine offenses are equal28

an d th at tr af fi ck ing in cr ac k in vol ve s di ff er en t r ea l c ondu ct

than tr af fi ck ing in pow de r. . . . C le ar ly , the n, Co ngr es s in te nde d th at part ic ular dis pari ty

to ex ist , and federa l courts are not fr ee to second-guess that ty pe of decision.”). T he district court’ s rej ection of the 100-to-1 d rug quantit y ratio, therefore , c annot be justified under § 355 3(a)( 6). W illiam s also contend s the district court didnot im perm issib ly

usurp Congress’ s policyj udgm ent because W illiam s was sentence d within the statuto ry ra n g e. He ar g u es th e 1 0 0 -t o -1 ra t i o embe d d edi nth e G u i d el i n es i s n o tCo n g re s s ’s policy , but the Sentencing Com m issio n’ s policy , one the Com m issio n has unanim ousl y

r ej ec te d. H e sugg es ts tha t the dis tr ic t c ourts c ane xe rc ise the ir se nte nc ing dis cr et ionto re j ec t the a dvi sor

y c ra ck c oc ai ne G uid el ine s w ith out ru nn in g a fo ul of C on gr es s’s p ol ic y jud gm en t. W ill iam s is inc or

re ct in sugg es tin g th e 100- to- 1 r at io e m be dde d inthe Gu i d el i n es i s m er el y th e S en t en ci n g Co m m i s s i o n ’s p o l i cy an dn o tCo n g re s s ’s policy . In determ ining the threshold q uantities for triggering th e statutory se nte nc ing r an ge s in§ 84 1( b) , Co ngr es s de ci de d ona100 -t o- 1 di ff er en tia l, and the Se nte nc ing Co m

m iss ionw as le ft

no c hoi ce but

to em plo y the sam e ratio in craf ti ng th e v ari ou s Gu id el in es ran ge s wi th in th os e st atut ory ran ge s. Se e id. a t 63 (“ As the Se ntencing Comm issio n recognized when it superim posed th e guidelines29

on the statut or

y f ram ew ork, it

w oul d be il log ic al to se t the m ax im um and m ini m um se nte nc es on o ne c onstru ct and the n to use som e oth er , e sse nti al ly an ti th et ic co ns tru ctas t he ba si s fo r fas hi on in g s en te nc es wit hi n t he ran ge .”). In de ed , Co ngr es s r ej ec te d th e Co m m iss ion ’ s pr opos al that w oul d have e quate d th e drugs for Guidelines purpos es because of the gross sentencing dis parities that w oul d r es ult

if the G uid el ine s di d no t e m plo y the sam e dr

ug quanti ty

r at io a s th e st atut ory sch em e. See H. R. Rep. No. 104-272 , at 4 (1995), re pri nte d in 1995 U . S. C. C. A . N . 335 , 337 . T he sam e is tru e if ins te ad of e quatin g th e tw o dr

ugs, the Gui de li ne s u se d adi ffer en t d ru g q ua nt it y rat io , say a 20 -to -1 rat io . Se e Pho , 433 F3d at 63-64. If

the Guidelines used a 20-to-1 ratio, a f irst tim e offe nder co nvi ct ed of se lli ng 5 0 gr am s of

c ra ck c oc ai ne ( the e qui va le nt o f one kil ogr am of pow de r co ca ine in our

hy pothe tic al ) w oul d have aG uid el ine s r an ge of 63 t o 78 m on th s’ im

pr is on m en t, see U. S. S. G. § 2D1.1(c )(7), but would have a m andatory m inim um sentence of 120 m onth s’ incarce ration under § 841 (b)(1)( A) . In co ntr as t, af

ir st t im e of

fe nde r co nvi ct ed

of se lli ng 4 9 gr am s of

c ra ck c oc ai ne ( the equivalent of 98 0 gram s of powder c ocaine in our hy poth etical) w ouldalso have a G uid el ine s r an ge of

63 t o 78 m onths’ im

pr iso nm en t, but

w oul d no t be sub

j ec t t o th e 1 20 -m on th m an da to ry m in im um . Se e id. § 84 1( b) (1 )( B) . I n th is s ce nari o, the differe nce of one gram

of cra ck cocaine w ouldresult in a sentencing dis parity of at30

least 42 m onth s. T hus, the statutory m inim um s and m axim

um s and the Guidelines refle ct Congress’ s policydecision to p unish cra ck offenses m ore severe ly than po wde r co cai ne off

en se s b y equa ti ng on e g ram

of c rackto 10 0 g ram s o f co cai ne . T he sam e unw ar

rante d di spari tie s be tw ee n si m ilarl y sit ua te d de fe ndants w oul d r es ult

if adis tr ic t c ourt w er e pe rm itt ed to use it s di sc re tio n to dis re gard the 100- to- 1 r at io. T hus, adis tr ic t c ourt’ s r ej ec tio n of the 100 -t o- 1 r at io e m

be dde d in the G uid el ine s no t on ly

c ount er m an ds C ongr es s’ s po lic y c hoi ce , but

a lso u n d erm i n es s en t en ci n g u n i fo rmit y i nd i re ct co n tra v en t i o no f § 3 5 5 3 (a )( 6 )’s com m and that dist rict courts seek to avoid unwarranted sentencing disp arities be twee n s im il arl y

si tu at edde fen da nt s. Se e Pho , 433 F . 3d at 63 -6 4; Eura , 440 F. 3d at 63 3 ( “ [G ] ivi ng a

se nte nc ing c ourt the auth or ity to se nte nc e a de fe ndant based on its view of an appropriate ratio betw een cr ack cocaine and po wder co ca ine w oul d in ev ita

bly r es ult in anunw ar

rante d di spari ty

be tw ee n si m ilarl y situated defendants in direct contradiction to the specific m andate of 18 U. S. C. § 35 53( a) (6 ). ”) . O f co ur se , som e dis pari ty be tw ee n si m ilarl y

sit ua te d de fe ndants is an inevitable result of Booker . See B ooker , 543 U . S. a t 26 3, 125 S . Ct . a t 76 6- 67 ( “ W e cannot

and d o no t c la im

that us e of

a‘ re as ona

ble ne ss’ standard

w ill pr ovi de the uni fo rm ity

that C ongr es s or igi na lly

sou ght to se cure . ”) . T his i n ev i t ab l e d i s p ar i ty, ho we v er , s h o u l do n l y b e t h e p ro du ct o f t h e d i s tri ct co u rt ’s31

dis cr et ionin w ei ghi ng i ndi vid ua liz ed § 35 53( a) f

ac tor s inagiv enc as e, not the consequence of the district court’ s “ general, acr oss-the-board pol icy considerations .” Pho , 433 F . 3d at 62 . W illiam s is correct that a sentence below the Guidelin es range in a c rack cocaine ca se m ay

be rea sonable, so long as it ref lects the indivi dualized, ca sespe ci fi c fa ct or s in§ 35 53( a) . I t m ay be that f or som e of the r ea sons state d inthe Se nte nc ing Co m

m iss ion ’ s r ep orts, the G uid el ine s r an ge in a giv enc ra ck c as e overstates the seriousness of the particular defendant’ s offense or that in di vi du al iz edm it ig at in g fa ct or s co un se l ag ai ns t a Gu id el in es sen te nc e. Se e Eura , 440 F. 3d at 63 7 ( Mi ch ae l, J. , c onc ur ri ng) ( “ Whil e the Co m

m iss ion ’ s f

ind ing s al one c annot

j ust if y abe low -g uid el ine s se nte nc e, in ce rt ai n c as es the y c anhe lp se nte nc ing c ourts ana ly ze the § 35 53( a) f ac tor s and s el ec t a

se nte nc e that i s

‘ suf fi ci en t, but

not gr eate r than ne ce ssary ’ to puni sh, de te r, and r eh ab ili ta te the de fe ndant. ”) . B ut t o say

Co ngr es s’ s c hoi ce of

a100 -t o- 1 dr

ug quanti ty

r at io i s never j ustified is a categorical re j ection of congression al policy , not an ind ivi dua liz ed , c as e- spe ci fi c co nsi de ratio n. C ongr es s c onc lud ed the 100 -t o- 1 r at io is j ust if ie d, and the c ourts h av e no a uth or ity to ch an ge that. Insho rt , the dis tr ic t c ourt e rr ed in m iti ga tin g W ill iam s’ se nte nc e ba se d on its pe rs ona l di sa gr ee m en t w ithCo ngr es s’ s po lic y de ci sio n to e m

plo y a100 -t o- 1,32

crac k-to-powder drug quantityratio in punis hing cra ck cocaine off enders m ore severely than powder cocaine of

fenders. In so doing , the district court im pe rm iss ibl y

usurp ed Co ngr es s’ s auth or ity

to se t se nte nc ing pol ic y

and f ai le d to properly consider § 355 3(a)( 6)’ s directive to avoid un warranted sentence dis pari tie s be tw ee n si m ilarl y sit ua te d de fe ndants . W e ag re e, m or eo ve r, w iththe Fo urth C ir cu it that “ al low ing se nte nc ing c ourts t o su bve rt Co ngr es s’ c le ar ly expr es se d w ill c er

ta inl y doe s no t pr om ote r es pe ct f or the law , pr ovi de j ust puni shm en t f

or the of fe nse of c onvi ct ion , or

r es ult in a se nte nc e re fl ec tiv e of the offense’ s seriousness as deem ed by Congress.” Id

. at 633 (m aj ority

opini on). ii . Ca re er

O ffe nde r G uid

el ine Prov isi on Appellant next argues the district court erre d in refusing to s entence W ill iam s a s ac ar ee r of

fe nde r. T he re is no d isp ute that W ill iam s qu al if ie d a s a care er off ender under U .S .S .G . § 4B1. 1. A t sentencing, however, the district court stated the care er off

ender enhancem ent “ is a totally inappropriate way

to consid er the ind ivi dua l natur e of

an of fe nse or ade fe ndant’ s in div idu al ba ck gr ound ” an d sa id i t w as not

goi ng t o se nte nc e W ill iam s a s ac ar ee r of fe nde r. I n it s se nte nc ing m em or an dum , the dis tr ic t c ourt a ga in e xpl ai ne d w ha t i t c onsi de re d to be the

“ arb it rary com

po un di ng ” eff

ectof t he care er o ffen de r en ha nc em en t. W il li ams , 372 F. Supp. 2d at 1339. T his, too, w as err or.33

Inc re at ing the S en te nc ing Co m m iss ionand c harg ing it

w ithe sta bli shi ng se nte nc ing pol ic ie s and p ra ct ic es f or the f ed er al c ri m ina l j ust ic e sy ste m , Co ngr es s dir ec te d th e Co m

m iss ionto: as sur e that the gui de lin es spe ci fy ase nte nc e to a

te rm of im prisonm ent at or near

the m axim

um term authorized for categories of defendants in which the defendant is eighteen y ears old or older an d— (1 ) ha s be enc onvi ct ed of af el ony that i s— (A ) a cr im e of

vio le nc e; or (B ) anof fe nse de sc ri be d inse ct ion401 of the Co ntr oll ed

S ubst an ce s A ct

( 21 U . S. C. 841 ) . . . ; and (2 ) ha s pr ev iou sly

be enc onvi ct ed

of tw o or m or e pr ior fe lon ie s, e ac h of

w hic h is

— (A ) a c rim e of violence; or (B ) anof fe nse de sc ri be d inse ct ion401 of the Co nt ro ll edSubs ta nc es Act (2 1 U.S.C. 8 41 ). . . . 28 U . S. C. § 99 4( h) . S ec tio n 99 4( h) r ef le ct s C ongr es s’ s po lic y

that r ep eat dr

ug of fe nde rs r ec ei ve se nte nc es “ at or ne ar ” the e nhanc ed

statut or y m ax im um s se t ou t in § 8 41 (b ). Se e U

nited Sta tes v . L aB ont e , 520 U . S. 751 , 762 , 117 S . Ct . 167 3, 16 79 (19 97 ) (h ol di ng “ th e p hr as e ‘at o r ne ar t he m ax im um term au th or iz ed ’ . . . re qui re s ac ourt t o se nte nc e a care er of fe nde r ‘ at or ne ar ’ the ‘ m ax im

um ’ pr iso n34

te rm a va ila ble onc e al l r el ev an t st at

uto ry se nte nc ing e nhanc em en ts are take n in to acco un t” ). Congress’ s goal was not sim ply to pun ish offenders with prior cr im inal histo ries m ore severe ly

than first tim e offe nders; Congress also wanted to target spe ci fi c re ci div ism , part ic ularl y r ep eat dr ug o ff en de rs . T he re is no que sti on W illiam s is a rec idivi st drug dealer. To the e xtent the dis trict court believed W ill iam s’ pr ior

c ri m ina l hi sto ry

w as a de quate ly

take n in to c onsi de ratio n inhis cr im ina l hi sto ry

c at eg or y of V I, it ign or ed Co ngr es s’ s po lic y

of targ et ing r ec idi vis t dr ug o ff en de rs f or m or e se ve re pun ish m en t. T he dis tr ic t c ourt, the re fo re , e rr ed in m itigatin g W illiam s’ sentence based on its dis agreem ent with the car eer offender G uid el ine s pr ovi sio n.

ii i. Se nte nc ing

F ac tor M ani pulati on Fi na lly , Appe llant arg ue s th e dis tr ic t c ourt e rr ed in m iti ga tin g W ill iam s’ se nte nc e ba se d onit s be lie f that the D E A“ snare d” W ill iam s by arr an gin g to pur ch as e cr ac k c oc ai ne f

ro m him , w he n apow de r co ca ine pur ch as e w oul d have be enc onsi ste nt w ithhis pr ior dr ug s al es . T he dis tr ic t c ourt’ s de ci sio n to m iti ga te W ill iam s’ se nte nc e be ca

use of the D E A ’ s c ondu ct

in inv es tig at ing W ill iam s c al ls to m ind a claim

we have ref

erre d to as “ sentencing factor m anipulatio n.” United States v. Sanchez , 13 8 F .3d14 10 , 14 14 (11 th Cir . 19 98 ).35

A sentencing fac tor m anipulatio n claim “ ‘ requires us to consid er whether the m an ipu la tio n inhe re nt i n asti ng o pe ratio n, e ve n if ins uf fi ci en tly opp re ssi ve to supp ort an e ntr ap m en t de fe nse , . . . or due pr oc es s c la im , . . . m ust som et im es be filtered out of the sentencing calculus.’ ” Id. (quot ing U nited Sta tes v . Co nne ll , 960 F. 2d 19 1, 194 (1st Cir. 1992 )). T he claim focuses on the Governm ent’ s conduct an d “poi nts to ‘ the opp ortun iti es that the se nte nc ing gui de lin es pos e fo r pr ose cu tor s to ge rr

ym an de r the dis tr ic t c ourt’ s se nte nc ing opt ion s and thus, defendant’ s sentences.’ ” I d. ( quot ing Co nne ll , 960 F. 2d at 194 ). W e ne ed not de ci de w he the r a fi ndi ng o f se nte nc ing f ac tor m an ipu la tio n is a valid m itigatin g consid eration under § 3553 (a) because, even if it can be, it w as not an a ppr opr ia te c onsi de ratio n he re . T he re is no que sti on W ill iam s’ arr es t and convictio n was the r esult of a valid sting operation, and the D EAno m ore

“ snared” W illiam s or engaged in sentencing fac tor m anipulatio n than in anyother s t i n g o p er at i o n . To s ay a d i s tri ct co u rtm ay fa ct o r i n t o a c ra ckco ca i n e o ff en d er ’s se nte nc e the bare f

ac t tha t the G ove rn m en t c hose to pur ch as e cr ac k in ste ad of pow de r co ca ine , w ith out

m or e, w oul d un de rm ine Co ngr es s’ s po lic y of pun ish ing cr ac k c oc ai ne of

fe nde rs m or e se ve re ly

and i m pe rm iss ibl y

int er fe re w iththe executive branch’ s perform ance of le gitim ate lawenforce m ent practices. Contrary to the dis tr ic t c ourt’ s c onc lus ion , it doe s no t pr om ote r es pe ct f or the lawto im

plyWe n ote that a ll f ive of Willi ams’ pr ior

fe lony c oc a ine c onvic tio ns lis te d in the PSI 13 inv olv e d c ra c k c oc a ine ; tw o o f t ho se we re c onvic tio ns fo r p os se ssi ngc ra c k c oc a ine wi th i nte nt t o se ll. 36 G ove rn m en t m isc ondu ct

f ro m the m er e fa ct

that the G ove rn m en t c hose to purchase cra ck cocaine fr om a cr ack dealer

instead of any

other controlled subs tanc e. T o th e ex te nt the dis tr ic t c ourt c onsi de re d th is f ac t a s am iti ga tin g 13 co nsi de ratio n, it

e rr ed a s am atte r of

law . T his is not

to say that se nte nc ing m anipulatio n m ay

never be a valid consi deration in sentencing . In this case, how ev er , it

w as e rr or

to m iti ga te W ill iam s’ se nte nc e ba se d onthe f ac t tha t the DE A purchased c rack c ocaine from W illiam s instead of powder cocaine. b. H arm less E rro r Be ca use Appe llant o bj ec te d to the dis tr ic t c ourt’ s c onsi de ratio n of the se im pe rm iss ibl e fa ct or s, it

is W ill iam s’ bur de n un de r our tr ad iti ona l harm le ss e rr or standard to show , ba se d onthe r ec or d a s aw hol e, that the e rr or s di d no t su bs ta nt ia ll y

affe ctth e d is tri ctco ur t’s ch oi ce o f se nt en ce. See M ath en ia , 409 F . 3d at12 92 . W il li am s h as fai le d t o m eethi s b ur de n. W ill iam s po int s to nothin g inthe r ec or d sh ow ing the e rr or s di d no t subs tanti al ly

a ff ec t the dis tr ic t c ourt’ s c hoi ce of se nte nc e. Ar ev ie wof

the sentencing transcript and th e district court’ s sentencing m em orandum instead show s th e dis tr ic t c ourt de vot ed the ove rwhe lm ing m aj or ity of it s e xpl an at ionof37

th e s e n t e n c e t o e x p r e s s i n g i t s d i s a g r e e men twi th th e c o c a i n e s e n t e n c i n g d i s p ar i ty, the c ar ee r of

fe nde r pr ovi sio n, and the D E A ’ s de ci sio n to pur ch as e cr ac k c oc ai ne from W illiam s. A lthou gh the record ref lects that the district court also consi dered ind ivi dua liz ed

f ac ts and c ir cum stanc es of W ill iam s’ c as e— suc h a s th e re la tiv el y s m al l amou n to f c ra ckco ca i n e i n v o l v edi nh i s o ff en s es —th e d i s tri ct co u rt ’s explana tio n of

W ill iam s’ se nte nc e w as so p er m eate d by

it s c onsi de ratio n of im perm issib le fac tors that we are unable to conclude the errors did not have a subs tanti al e ff

ec t onit s c hoi ce of

se nte nc e. T he e rr or s are , the re fo re , not harm le ss, and we m ust vacate the sentence and re m and for the district court to resentence W ill iam s so le ly

on the ba sis of

the ind ivi dua liz ed

f ac ts and c ir cum stanc es of W il li am s’ cas e b eari ng on th e § 35 53 (a) fa ct or s. 2. Unreasonab le Length of the Sentence H av ing c onc lud ed

W ill iam s’ se nte nc e is unr ea sona ble be ca use it is ba se d on im pe rm iss ibl e fa ct or s, w e do n ot r ea chAppe llant’ s a lte rn at ive arg um en t tha t, as sum ing the dis tr ic t c ourt c onsi de re d on ly pr ope r fa ct or s inc ra ft ing W ill iam s’ se nte nc e, the le ngth of

the se nte nc e is n ev er

the le ss unr ea sona

ble be ca use the re co rdd o es n o tju s t i fy an y d ev i at i o nfr o m th e a d v i s o ry Gu i d el i n es ra n g e. We expr es s no opi nio n a s to w he the r the re are ind ivi dua l f ac ts and c ir cum stanc es in W il li am s’ cas e th atwou ldm ak e a 2 04 -m on th sen te nc e rea so nabl e.38 IV. C ONC LUS ION W e conclude, a fter a

de novo review, that the district court consid ered im pe rm iss ibl e fa ct or s inc ra ft ing W ill iam s’ se nte nc e. B ec au se W ill iam s f ai le d to show, based on the rec ord as a whole, that the err ors did no t subs tantially aff ect th e d is tri ctco ur t’s ch oi ce o f se nt en ce, we co nc lu de th e err or s ar e n otha rm le ss . W e, the re fo re , va cate W ill iam s’ se nte nc e as unr ea sona ble w ith out

r ea ch ing Appe llant’ s a lte rn at ive arg um en t tha t the r ec or d do es not j ust if y the le ngth of

the sentence im

posed. On r em and, the district court m ust resentence W illiam s based on the ind ivi dua l f

ac ts and c ir cum stanc es of W ill iam s’ c as e be ar ing on the § 355 3(a) f

actors. W e express no opin ion as to what sentence the district court shou ld i m pose a ft er pr ope rl y appl y ing the § 35 53( a) f ac tor s. VACATED AND REMANDED.