The Hono r ab l e J o se ph Va n Bo k k el en, Uni te d S ta te s Di st r i ctCo ur t J udg e f o r the * N o r th ern Di st r i cto fI ndi an a, s i tt i ngb y de si gna ti o n. 

# United States Court of App eals

F orth eSeve nt h Ci r c uit Chicago, Illin ois 60604 A rgued M ay 14, 20 09 Deci ded A ugust 4, 20 09 B efo re I L A N A D IA M O N D R O V N E R, Cir cu i tJudg e TE R E N C E T . E V A N S , Cir cu i tJudg e JO SE P H V A N B O K K E L E N , D i s t r i ctJudg e * N o. 08
- 4238 U N IT E D ST A T E S O F A M E R IC A ,

P la intif f-A pp ellee,
v. D E M A R K O ST E W A R D ,

D ef endant-Appellant
. A pp ealfro m the U ni ted S tat es Dist ri ct Court f orthe So uthern Dist ri ct o fI l l i noi s. N o. 08 CR 30 060 J. Ph il G ilbe rt, Judg e .
OR D ER Dem ar ko St ew ar d, a s m al l
- ti m e drug tr affi cker, was sente nced to a t er m o f20 0 m o nths a fte r the di st r i ctc o ur t co nc l ude d tha t he was a c ar ee r o ffen derunde r the se nt en ci ngg ui del i ne s. S te war d a ppea l s hi s se nt en ce b y mount i ng, a s he di d b efo r e th e dist ri ct c ourt, a sw eepi ng at tacko n the use o fthe car eero ffender enhancem ent o n l ow-l eve l NONP RE C E DE NT I AL DI S PO S I T I ON To b e ci te d o nl y i n a cc o r dan ce wi th Fe d . R. A p p . P. 32 .1N o. 08
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### Pag e 2

drug deal er s l i ke hi m sel fand ar gui ng tha t the co urt acco rded the enhancem ent undue w ei ght. I n 2 00 5, the po l i ce s etup th r ee c o nt r o l l ed buy s th r o ug h a c o nfi den ti ali nf o r m an t an d an undercov ero ffi cero vera f our- m onth per i od, with S teward as thei r tar get . The b uys wer e a su cc es s- - S te war d s o l d 1 1. 5 g r ams o fc r ac kc o ca i ne a nd 1
. 2 g r ams o fc o ca i ne . Ono ne o cc as i o n h e al so b r o k er ed th e sa l e o fa n i no per ab l e ha ndg un. S te war d r ec ei ve d the g un in a coca i ne dealand then i m m edi ate l y r eso l d i t t o the info rm ant f or$8 0. Tw o yea rs l ate r S te war d was i ndi ct ed f o r di st r ibut i ngc r ac kc o ca i ne ( two c o unt s) , di st r ibut i ngc o ca i ne , a nd b ein g a felon in p os se ss ion of a fire ar m . See 2 1 U. S
. C
. § 8 4 1 ( a ) ( 1 ) ; 1 8 U. S
. C
. § 9 2 2 ( g ) ( 1 )
. H e ple aded gui l ty to al l co unts. A pro bati on o ffi cerpre pared a prese ntence re port, not i ng tha t S teward w as a ca re er offender si nce he had thre e pr i orst ate co nvi cti ons f orposs ess i on with i ntent to del i ver ei therco cai ne o r m ar ij uana. U.S
. S. G. § 4 B1. 1. But l i ke the c harg ed conduct, thes e pr i or drug tr affi cki ng co nvi cti ons showed thathe w as no l ar ge- scal e di str ibutor
. In to tal ( co m bi ni nga l l thr ee c o nv i ct i o ns ) , S te war d was c au g htwi thl es s th an6 g r ams o fc o ca i ne an d l es s th an2 5 g r ams o fmar ij ua na . Ba se d o n the c ar ee r o ffen dere nha nc ement, the proba ti on o ffi cercal cul ate d Ste w ar d’s gui del i nes r ange to be 1 88 to 235 m onths of i m pri sonm ent. W er e he not a ca re ero ffender, the ra nge woul d have be en 10 0 t o 125 m o nths o fi nc ar ce r at i o n. S t e wa r d o b j e c t e d t o th e P S R, a r g u i n gth a tth e c a r e e r o ffe n d e r e n h a n c e me n t, f o r l o wl ev elr et ai l t r affi ck er s, was f at al l y fl awe d. He co nt en ded th ata t i ts i nc ept i o n the enhancem ent, l i ke the 1 00- 1 cr ack to pow der c oca i ne se ntenci ng r ati o, l acke d em pir i cal su p p or t a n d cit ed a Se n te n c in g C om m iss ion rep or t q u es tio n in g its u se in c as es like h is. U . S. S EN T EN CI NG C OM M ’ N , F I FT EE N Y EARSOF G UID ELINE S S EN T EN CI NG : A N A S S E S S ME NTOF H OW W ELL THE F EDERAL C RI MINAL J UST ICE S YSTEM IS A CHIEVI NG THE G OALS OF S EN T EN CI NG R EFO RM 1 33
- 34 ( 20 04 )
. T he g o ve r nm en t r es po nde d b y po i nt i ngo uttha t th e enha nc ement techni cal l y a pp l i ed-- a f act that St ew ar d did not dispute-
- and that the co urt had an ob liga tio n to ac c u ra te ly c alc u lat e t h e g u id elin es ran ge be for e im p os in g St ew ar d ’s s en te n c e. I n i ts vi ew , S teward’s co ntenti on was m er el y a “s entenci ng ar gum ent m asquer adingas a PS R o bj ec ti o n. ” S te war d, ho wev er, a l so made a st r ai g ht f o r war d s en te nc i nga r g um en t i n a sep arate sta tem en t of m iti gating factors
. Th ere, he argue d that the en ha nc em en t’s appl i ca ti o n r es ul te d i n a s en te nc e g r ea te r tha n n ec es sa r y, i n c o nt r av en ti o n t o the s en te nc i ng f acto rs l i ste d i n 18 U . S. C. § 3 553( a)
. He re i ter ate d his at tacko n the car eero ffender gui del i nes b ut al so poi nted to hi s t ough chi l dh oo d, w hi ch i ncl ud ed abuse at the hands o f alc oh olic p ar en ts an d st in ts in fo st er ca re , as w ell as h is a c tiv e p u rs u it of d ru g t re at m en t. U l ti m ate l y, he a rgued fo r a s entence o f10 0 m onths, the bot tom o fhi s unenhanced gui del i nes r ange.N o. 08
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### Pag e 3

A t s en te n c in g t h e d ist ric t c ou rtfirst d ea lt w ith Ste w ar d ’s o b j ec tio n s t o t h e P SR
. N oting tha t he fel l withi n the am bi t o fthe car eero ffender enhancem ent, the cour t a gr eed w i th the pro bati on o ffi cerand the gov er nm ent a nd se t the gui del i nes r ange at 188 to 235 m onths. In re achi ng thi s deci si on, the cour t s tat ed that “i fthe car eero ffender sta tus under the guidel i nes, the l aw , i s g oi ng to be changed, i t’ s no t g oi ng to [ be] by thi s Court
. ” I t then pr o cl ai m ed th ati t ha d “ co ns i der ed al l the i nf o r m at i o n i n the pr es en te nc e r epo r t i nc l udi ng gu ideline com p ut ations an d f acto rs set forth in 18 U
. S. C
. § 3553(a)” and sent en ced Stew ard to 200 m onths. The c ourtpro vi ded no furtheranal ysi s o fthe sta tutor y s entenci ng f acto rs , nordi d i t m enti on a ny o fS teward’s ar gum ents und ertho se f acto rs . O n ap p ea l Ste w ar d ren ew s h is w h ole sa le a tt ac k on th e c ar ee r offe n d er gu id elin es . A di st r i ctc o ur t’ s dut i es a t se nt en ci nga r e two f o l d: fi r st, the c o ur t m us t co r r ec tl y c al cul at e th e appl i cabl e g ui del i ne s r an g e; s ec o ndl y, i t m us t m ak e ani ndi vi dual i ze d a ss es smento fthe defe nd ant, i n l i ght o fthe sente nci ng f acto rs l i ste d i n 18 U . S. C. § 3 553( a) , to ar ri ve at a r ea so nabl e se nt en ce a nd a dequa te l y e xpl ain the c ho se n s en te nc e to a l l o w f o r mean i ng ful re vie w . G a ll v. U nited Sta tes , 1 28 S
. Ct
. 5 86 , 5 96
- 97( 20 07 )
. Be ca us e S te war d s ee m s to a r g ue that the c ar eero ffender gui del i nes a re so fl aw ed that they shoul d have be en i gnor ed at both ste ps, we turn t o the di str i ct c ourt ’ s e xecuti on o fthi s t w o- ste p proce ss. As a n i ni ti almatt er, the c o ur t co r r ec tl y a ppl i ed th e enha nc ementwhenc al cul at i ng the guidel i nes r ange. S teward adm i ts that he te chnic al l y fi ts und erthe car eero ffender gui del i ne, and the dist ri ct c ourtwas not f re e t o i gnor e thi s f act- - i t i s wel l
- set tl ed ( as w e’ ve j us t note d ) th at th e d istri ct cou rt’s first obl igation i s to correctly calculate th e d efend an t’s gu id elin es ran ge , as t h ey st an d
. G all , 128 S. C t. at 59 6; U nited Sta tes v. Sa ch senm a ier, 49 1 F . 3d 68 0, 6 85 ( 7th Ci r . 2 00 7)
. T he c o ur t’ s st at ementtha t th e ca r ee r o ffen ders ta tu s enha nc ement i s “ the l aw ” was not, as S teward ar gues on a pp eal, a re vel ati on o fi ts m i sta ken b el i efthat the guidel i nes were m andator y. In f act, duri ng bo th the se ntenci ng hea ri ng and the change o fpl ea he ar i ng, the c o ur t ex pl i ci tl y r ec o g ni ze d tha t th eya r e adv i so r y . R athe r, the sta tem ent m er el y r eaffi rm s the co urt’ s o bl i gat i on t o accura tel y c al cul ate the gui del i nes ra nge duri ng the se ntenci ng hea ri ng. Bu t the co urt’ s duti es do not end afterthe gui del i nes a re cal cul ate d. The gui del i nes provi de i nsi ght forf ashi oni ng an appropri ate se ntence, but the punis hm ent m ust ul ti m at el y b e ba se d o n § 3 55 3( a) “ wi th o uta ny thumb o n the s ca l e f av o r i nga g ui del i ne sente nce. ” Sa ch senm a ier, 491 F.3d at68 5; see also Nelson v. U nited Sta tes , 12 9 S
. Ct. 89 0, 89 2 ( 2009 )
. S teward not onl y a tta cked the gui del i nes c al cul ati on, but he al so m ai ntai ned that th e c alc u lat ion yield ed a p u n ish m en t g re at er th an n ec es sa ry , con tr av en in g § 35 53 (a). St ew ar d rene w s thi s a rgum ent o n appeal, and so we m ust r evi ew hi s s entence f oran abuseN o. 08
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o fdi sc r et i o n, r emandi ngf o r r es en te nc i ngo nl y i fthe di st r i ctc o ur t f ai l ed to c o ns i derthe st at u to ry fac to rs or fa iled to ad eq u at ely ex p lain th e c h os en se n te n c e. G all , 12 8 S
. Ct. at59 7. On this r eco rd, we re l uctantl y fi nd an abuse o fdi scr eti on. The c ourt ’ s e nti re § 35 53 (a) a n aly sis co n sis ts of a fra gm en t o f a se n te n c e, w h er e itm en tio n s in p as sin g t h at it c on sid er ed th e s ta tu to ry fac to rs . T ru e, a c ou rtn ee d n otbe lab or its an aly sis , U ni t e d S t at e s v. D e an , 41 4 F . 3d 725, 72 9 ( 7th Ci r. 20 05) , but i t m ust e xplai n i ts deci si on a dequ ate l y e nough to allo w for a p p ella te rev iew , U ni t e d S t at e s v. Cunn i ngh am , 42 9 F . 3d 673, 67 9 ( 7th Ci r. 20 05) ( “A r o te s ta te m en t th atthe j udg e co ns i der ed al l r el ev an t f ac to r s wi l l no t al way s su ffi ce ; the te m pta ti o n t o a b us y j udg e to i m po se the g ui del i ne s se nt en ce a nd b e do ne wi thi t, wi th o ut w adingi nto the v ague and prol i x sta tutor y f acto rs , cannotbe i gnor ed. ”)
. And wh i l e a dist ri ct c ourti s fre e t o gl oss o veri nsubstanti alar gum ents, i gnor i ng a defe nd ant’ s princi pal conte nti on i s no t wis e. H er e, St ew ar d p re se n te d u n re b u tt ed ev id en c e t h at h e w as a sm all-t im e d ru g d ea ler
. H is p rior d ist rib u tio n co n vic tio n s--t h e c rim es th at m ad e h im a c ar ee r offe n d er --in vo lve d , in to ta l, a r o und a s ho t g l as s ful l o fi l l eg als ubs ta nc es . S te war d a l so po i nt ed to the S en te nc i ng Com m i ssi on’ s o w n re port, questi oni ng the effi cacy o fusi ng drug tr affi cki ng co nvi cti ons, esp eciall y for retail- level traffi ckers, to qu ali fy a d efend an t for career offend er statu s. U . S. S EN T EN CI NG C OM M ’ N , sup ra , at 133- 34. The Com m i ssi on not ed that the g oalo f i ncapaci tat i ng cr i m i nal s was underm i ned si nce, unl i ke re peat v i ol ent o ffenders ( w ho a l so quali fy a s ca re ero ffenders) , r eta i l
- l eve l drug tr affi cker s a re r eadi l y r epl aced. Li kewis e, prel i m i naryr ese ar ch sugg est s that the r eci vi dism r ate s f ordrug tr affi cker s s entence d as car eero ffenders ar e m uch l ower than other offenders w ho a re si m i l ar l y a ssi gned to a cri m i nal hi sto rycat ego ryVI . And o n to p ofthi s g ener al i zed ev i dence, the PSR not es that S te war d, who was r ec ei vingdr ugt r ea tment, was no t o nl y c o m pl i an t, b uttha t he s pen t ex tra tim e trying to get straight. A ccord ing to his health care p rovide rs, he seem ed “very sin c er e in h is e ffor ts to ch an ge h is life a n d be a b et te r fat h er .” These f acts add up to a nonf ri vol ous a rgum ent fora sente nce a t the l ow end , o r eve n below , the gu idelines ran ge. A fter U nited Sta tes v. B o o k er, 54 3 U.S
. 22 0 ( 2005 ) , the dist ri ct c ou rtis fre e t o, infac t re q u ire d to , l oo k b ey on d a d efe n d an t’s ca re er offe n d er st at u s, to h is in d ivid u al s itu at ion to d et er m in e a rea so n ab le s en te n c e u n d er § 35 53 . Se eU ni t e d S t at e s v. Liddel l , 54 3 F . 3d 877, 88 4- 85 ( 7th Ci r. 20 08) ( hol ding that al l o fthe sente nci ng g uidel i nes, in c lu d in g t h e c ar ee r offe n d er en h an c em en t, ar e a d vis or y); U nite d State s v. Harris , 53 6 F . 3d 798, 81 3 ( 7th Ci r. 20 08) ( sam e)
. That sta tute re quir es the di str i ct c ourtto “i m pose a sente nce s uffi ci ent, but not gr eat erthan necess ar y, ” t aki ng i nto acco unt ( am ong othe r th i ng s) the de fen dan t’ s hi st o r y a nd the ne ed to pr o te ctthe pub l i c f r o m fur th erc r i m es o fthe d efe n d an t. Seeid
. at( a) ( 1) , ( a) ( 2) ( C). S teward’s well
- supp or ted pl ea f ora 100- m onthN o. 08
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s e nt e nc e f o c us e d o n the s e t wo f a c t o r s , b utthe c o ur tp a s s e d o v e r h i s r e qu e s ti n s i l e nc e . B y doi ng so we cannot be s ure that the c ourtexer ci sed i ts disc re ti on ( that i s, ev en co nsi dered the f acto rs r el evantto se ntenci ng r ai sed byS teward), l et al one w hetheri t abused i ts disc re ti on i n doi ng so . Thi s s hor tco m i ng pre cl ud es affi rm i ng S teward’s se ntence. Of c ours e, r eas onabl eness i s a r ange, nota poi nt, and w e r eco gni ze that the s entence i m po se d b y the j udg e m ay, i ffur th ere xpl aine d, pa ss must er . We e xpr es s no v i ew o n the properse ntence and hol d onl y that the co urt m ust a dequ ate l y e xplai n i ts sente nce under § 3 553( a)
. Accordi ngl y, the j ud gm ent o fthe dist ri ct c ourti s VAC AT E D an d th e c as e is RE MANDE D f orr ese ntenci ng.