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# United States Court of Appeals For the Seventh Circuit

No. 15-1580

U NI T E D S TAT E SOF A M E RI C A , Plaintiff-Appellee ,

v.

O R L AND O R O SAL E S

, Defen dant-Appellant.
Appe al f ro m the Uni ted S tates Distri ct Co urt fo r the

Western Di stric t o f Wi sconsi n No. 3: 14 -cr- 00 11 4- b b c-1 — Barba ra B. Crabb , Judg e.

A RGU E D N OV E MB E R 10, 2015

— D E C I D E D F E B R UAR Y 11, 2016

Before P O S N E R

, E A S T E R

B R O O K , and R OVN E R

, Circ uit Judges. R OVN E R , Cir cui t Judge

. O r l a ndo Rosales pleaded gui lty to
a charge that he conspi red to possess, wi th intent to di strib ute, 500 gr ams or more of cocaine, and w as sen tenced to a ter m of 120 months i n pris on. He appeals the sentence, contendi ng that t he di stric t court commi tte d procedural err or by not giving
a d e quate reasons for rej ecti ng hi s contention that he sh ou l d n ot be sentenced as a career o ffender . W e affi rm.2 No. 15-1580
I. Rosales play ed a managerial ro le in a small cocaine tr affi cki ng ring i n S a uk County , Wi scons in. Wi th the assi stance of three other i ndi vidu als, Rosal e s o bt ained cocaine from tw o di fferent supp li ers, one in Chi cago and one in M a d iso n, Wi scons i n, and then di strib uted i t to hi s cus tomer s in Wi sconsin. R osales’s drug tr affi cki ng w as exposed when in di vidu als cooper atin g wi th the g o ver nment i denti fi ed hi s Chi cago connecti on as a cocaine supp li er and named Rosales as one of the supp li er’s cus tomer s. The Chi cago supp li er w as arr ested after a confi denti al i nformant arranged a contro lled purchas e of cocaine from hi m; he in turn confi rmed that he had supp li ed
coca ine to Rosales on multi ple occasi ons. Rosales w as ulti

mately charged i n a one-count information wi th conspi ra cy wi th the i ntent to di strib ute in e xcess of 5 0 0 g r ams of cocaine from August 2011 to Nov ember 2013. He pleaded gui lty to that charge p ur su ant to a wri tte n plea agr eement in whi ch he agr eed to w ai v e i ndi ct ment and cooper ate wi th the government (Rosales ai ded the government in the prosecuti on of the supp li er wh o fingere d hi m) and in whi ch the government agr eed to recommend that he be giv en maxi mum credi t for acceptanc e of responsibi li ty and that hi s sentence be reduced i n recog ni tion of hi s sub stanti al assi stance to the government. Pursu ant to the Sente ncing Gui delines, Rosal e s faced an advis or y sentence of between 188 and 235 months. The range

w o ul d hav e been low er—140 to 175 months—abs ent a thr e e lev el i ncrease in hi s offense lev el resulti ng from the careerNo. 15-1580 3
offender gu ide line. U.S.S .G. § 4B1.1. Generally , the career 1 offender gui deline appli es when the defendant (1) w as at least 18 y ears old when he commi tt e d the instant offense; (2) the i nstant offense i s a felony that i s ei ther a cri me of violence or a contro lled sub stance offense; and (3) the defendant has at least tw o prior felony convic tions that q ua l ify ei ther as a cri me of violence or a contro lled sub stance offense. § 4B1.1(a). A contro lled sub stance offense i s defined to inclu d e a felony offe ns e t hat, as relev ant here, inv olv es the possess i on of a contro lled subst a nce wi th the intent to di strib ute. § 4B1.2(b)

. Th e cr i me to whi ch Rosales pleaded gui lty in thi s case of
course quali fi es as a contro lled sub stance offense, and Rosales had three such prior convic tions

. In 2004 and 2008, he had been convic ted of possess i ng, wi th the intent to di strib ute, less than 200 gr ams and more than 2,500 gr ams of mari juana, respectiv ely; and i n 2011, he had been c onvicted of posses sing, wi th the i ntent to di strib ute, betw een one and fi v e gr ams of cocaine. The presentence repo rt remin ded t he d istric t judge that she had the di screti on to d isagree wi th the poli cy reflected in the
career offender gui deline when she sentenced Rosales. R. 14 at 29 ¶ 149; R. 15 at 29 ¶ 151. In a wri tte n memorandum fi led prior to sentencing, and again in hi s or al remark s at the sentencing hearin g, Rosales’s
couns el asked the court, on tw o separate but relat ed gr ounds, to di sregar d the sentencing increase called for by the career

Appl i catio n of the career of fender guid el i ne also di ctated tha t Rosales b e 1

ass i gned to the top cri minal histo ry category of VI, b ut the extent o f hi s cri minal hi st o r y woul d hav e pl aced him i n category VI regardl ess of the
career o ffe nder d esi gna tio n.4 No. 15-1580
offender gui deline. The fi rst of these w as a poli cy-bas ed challen ge to the career offender g uideline i tself, posi tin g that the gui deline w as adopted wi thout empi ric al research and careful study

, and repr esented uns ound poli cy to the ext ent i t appli ed not only to large -sc ale drug tr affi ckers but also to relat i v ely low-lev el offenders who, li ke Rosa l es, tr affi cked in drugs prim arily to su pport their own drug habi ts and di d not reap large amounts of money from their drug-deali ng. The second w as an as-ap p li ed challen ge, whi ch arg ued that the
career offender desi gnation w a s inappropr i ate in Rosales’s case, giv en that hi s predic ate drug-tr a ffic kin g convic tions i nv olv ed relat i v ely modest amounts of mari juana and cocaine; that he had no hi stor y of violence; that hi s drug dealings w ere driv en by a ne e d t o supp or t hi mself , hi s fami ly

, and hi s own drug, alc ohol, and gambling h abi ts; that hi s supp li er recei v ed only a 48-mont h sentence; and gener ally that a lengthier
s e n te n c e wa s in c ons i stent wi th the sentencing factors i denti fi e d in 18 U.S.C. § 3553(a). Counsel propo sed that Rosales be sentenced to a ter m of si x y ears. Th e di stric t court, after hearin g the parties at sentencing , adopted the pre-sentence repo rt, appli ed the career offender gui deline in deter mining Rosales’s advis or y sentencing range, gr anted the government’s motion for a multi -lev el downw ard

v a rianc e from the Gui delines range based on hi s sub stanti al

a ss ist a nce, and or dered Rosales to serv e a sentence of 120 months i n p r iso n, to be follow ed by a four -y ear period of supervis ed release. After announc ing the sentence, the di stric t j ud ge asked defense couns el whether he “ha[d] any speci fic objections to the sentence or to the condi tions [of supervis ed release] that y ou hav en’t alr eady mentioned.” R. 36 at 27.No. 15-1580 5
MR. MANDELL: I don’t[,] other than I don’t know

why the court appli ed the career offender gui deline other than the p ri or convic tions under the in formati on I pr ov i ded, but – THE COUR T : That’s a goo d questi on. I appli ed

the career o ffender gui deline[ ] becau se Mr

. Rosales’s cri minal conduc t justifi ed the appli cati on. MR. M ANDELL: E ven t ho ug h t he pr io r co nv ictions w ere for relat i v ely minor offenses ? THE COURT : Ri ght. MR. M ANDELL: Okay

. R. 36 at 27-28. II. Rosales contends that the di stric t court err ed procedurally at hi s sentencing by not adequately art i culating i ts reasons for rej ecti ng hi s arg ument that the career offender gui deline should not be appli ed in hi s case giv en the relat i v ely minor nature o f hi s predi cate convic tions

. A di stric t court i s required at sentencing to address the defendant’s prin ci pal arg um e nt s in mi tigati on unles s those

a r g uments are wi thout factual foundati on or are too w eak t o require d isc ussi on. United States v
. Cun nin gham , 429 F .3d 673, 6 7 9 (7 th Ci r
. 2005). Thi s obli gation func tions as a safeguar d ensuring that the di stric t judge has not ov erlo o k e d a nd has6 No. 15-1580 actually consi dered the prin ci pal i ssu es informi ng her sentenci ng deci si on. United States v
. Donelli, 747 F .3d 936, 940 (7th Ci r
. 2014). “The requirement i s based on the view that a ‘judge who fai ls to menti on a gr ound of recog ni zed legal m erit (prov i ded i t has a factual basi s) i s li kely to have co mm it t ed an err or or
ov ersi ght.’” Id. (quoti ng Cun nin gham , 429 F .3d at 679). Fr equently

, a defendant’s prin ci pal arg ument in mi tigati on take s the form of a challen ge to the Gui deline s themselv es. After United States v
. Boo ker , 543 U.S. 220, 125 S. Ct. 738 (2005),
a sentencing judge has the di screti on to di sagree ei ther wi th a particu lar prov i si on of the S e nt e ncing Gui delines, Kimbrough

v
. United States , 552 U.S. 85, 128 S. Ct. 558 (2007), or the
se nt e ncin g range that results from appli cati on of the Gui de

lines as a whole, Rita v
. Unit e d S ta tes , 551 U.S. 338, 351, 127 S. Ct. 2456, 2465 (2007), a nd t o i mpose a non-Gu i delines sent e nce that, in her judgment, i s more consi stent wi th the st a t utor y sentencing factors set out in 18 U.S.C. § 3553(a). S e e United States v
. Corner, 598 F .3d 4 11, 416 (7th Ci r
. 2010) (en banc ). The judge’ s authority to di sagree wi th the Gui delines ext ends to the career offender gui deline at i ssu e here. See id. Th e court i s not obli ged to address all such arg uments questioning the reasonableness of Gui delines prov i si ons. The court may pass ove r i n si lence a blanket poli cy challen ge li ke Rosales’s arg ument that the career offender g ui deline w as poor ly concei v ed and i s ov erbro ad. See United States v
. Estrada

Mederos , 784 F .3d 1086, 1088 (7th Ci r
. 2015) (collecting ca se s). B ut a n as-app li ed challen ge to a gui deline, prov i ded i t i s gr ounded i n the facts of the case, not fri v olous, and adequately presented to the court, i s one that must be addressed. See Unite d States v
. Schm itz, 717 F .3d 536, 542 (7th Ci r
. 2013)No. 15-1580 7 (di sti ngui shing betw een catego ric al and as-app li ed challen ges to gui deline); see a lso , e.g. , United Stat es v
. Morris , 775 F .3d 882, 887 (7th Ci r
. 2015) (vacati ng sentence and remandi ng where di stric t court fai led to address defendant’ s arg ument that crack-to-powder cocaine rat i o resulted in excessiv e sentencing range giv en that mo st o f drug quanti ty attr ibuted to hi m compri sed coun ter fei t crack cocai ne). Arg uments thata sentencing court commi tte d procedural

err or of the Cun nin gham v ariety , by fai ling to address a defendant’s prin ci pal arg ument in mi tigati on, inclu ding challenges to the Gui delines, hav e become a staple in th i s court. See Donelli, 747 F .3d at 941 (ci tin g United States v
. Castaldi, 743 F .3d 589, 595 (7th Ci r
. 2014)). And y et i t i s a relat i v ely si mple matter fo r a di stric t judge to obviate such an appellate arg ument by ensuring, before the close of the sentencing hearin g, that sh e has addressed each of the defendant’s prin ci pal arg uments in mi tigati on. T

o that end, w e suggested in United States v
. GarciaSegu ra , 717 F .3d 566, 569 (7th Ci r
. 2013), that th e judge ask defense couns el whether he or she i s sati sfi ed that the court has adequately addr e ssed the main arg uments in mi tigati on. If
couns el replies i n t he affi rmativ e, a contention on appeal that the di st r ict court fai led to address a prin ci pal arg ument in mi tigati on w ould be deemed w ai v ed. Id. If couns el replies in the negativ e, then that w ould giv e the court the oppor tuni ty to make clear ei ther why i t di d not view the arg ument as w arr anti ng di scu ssi on or why it had rej ected the arg ument on i ts merits. Id. In thi s case, the di stric t judge di d not pose qui te the inqui ry
w e suggested i n Garcia-Seg ura when she asked i f there w ere8 No. 15-1580 “any speci fi c o bjections ” to the sentence t hat d e fe nse counsel hadn’t menti oned, see Morris , 775 F .3d at 886; but nonetheless defense couns el too k the oppor tuni ty to inqui re why the judge had sentenced Rosales as a career offender

. The j udge in t urn
r e mar ked that she appli ed the career offender gui deline becau se she thought that Rosa l es’s cri minal conduc t justifi ed i t, notwi thstanding (at defense couns el’s p r omptin g) that hi s predic ate crimes were, in c ounsel’s vi ew , relat i v ely mi nor
. In view of thi s exchange, there can b e no qu esti on that the di stric t court consi der e d a nd rej ected Rosales’s prin ci pal arg ument i n mi tigati on. The court plainly understood that i t had the di screti on not to sentence Rosales as a career offender , di screti on that w as hi ghli ghted both in Rosales’s se nt encing memorandum and the probati on offi cer’s presentence repo rt

. And the di stric t judge qui te clearly indi cated that she beli ev ed i t appropr i ate to adhere to the ca r e e r offender gui deline in sentencing Rosales. The only i ssu e i s the adequacy of the judge’ s explanation. Defens e co un sel perhaps could hav e pressed the judge to say more than she di d, but havin g already prompte d the court for an explanation, w e do not fault hi m for letting the matter rest once the court indi cated that i t had rej ected the ar gument on its m erits. A court’s obli gation t o address a defendant’s prin ci pal arg ument i n mi tigati on does inclu de giving reasons for why i t has rej ected that a rg ument. See Garcia-Segura , 717 F .3d at 569 (ci tin g Cun nin gham , 429 F .3d at 679) ; see also , e.g. , United Stat es
v
. Thomas , 794 F .3d 705, 713 (7th Ci r .) (ci tin g Morris , 775 F .3d at 886-88), cert. d enied, 136 S. Ct. 558 (2015). In thi s case, the court’s explanation that i t hew ed to the career offender gui deline becau se Rosales’s conduc t j us tifi ed i t arg uablyNo. 15-1580 9
amounted to ipse dixit, in that the cour t did not ar ticulate why i t viewed hi s conduct as support ing appli ca t io n of the gui deline. Cf. United States v
. Jones , 798 F .3d 6 1 3 , 6 1 8 (7th Ci r
. 2015) (a lthough recor d made clear di stric t court consi dered defe ndant’s mi tig a t io n arg uments but rej ected them, court di d not di rectly explain why i t found them unpersuas i v e). But for tw o
reaso ns w e are sati sfi ed that any Cun nin gham err or w as har mless

. See Morris , 775 F .3d at 885 (procedural err or at sentencing i s subject to harmless- err or rev i ew). First, Rosales’s as-app li ed challen ge t o the career offender gui deline ov erlapped sub stanti ally wit h hi s poli cy arg ument and w ould apply equally to many offenders. As hi s sentencing memorandum i tself posi ted, becau se the career offender gui deline comes i nto play whenev er a defendant has tw o prior convic tions fo r a drug tr affi cking offense, reg ardless of the drug quanti ty i nv olv ed , the gui deline wi ll apply to countless low-lev el offenders who are poor , addi cted to narcotic s, a nd
resor t to t r affi cki ng to supp or t themselv es and their fami li es, not to menti on their addi cti ons. So vis -à-vi s t he purpor ted
ov erbre adth of the g ui deline, Rosales’s c ase di d not present a particu larly uni que o r compelling set of ci rcums tances that required di scu ssi on. T o be sure, the court w as oblig e d to consi der Rosales’s personal characteris tic s and hi stor y in
arr i ving at an appropr i ate sentence, i rr especti v e of how much he may hav e had i n common wi th other lo w-lev el, repeat di strib utor s of narcotics who quali fy as career o ff e nders. See § 3553(a)( 1). But the c ou rt p l a inl y compli ed wi th that obli gation here: i t address ed Rosales’s indi vidu al ci rcums tances, inclu di ng hi s drug and alcohol addi cti ons, at some length in arr i ving at the sentence. R. 36 at 17-18, 21-22.10 No. 15-1580 Second, the recor d other wi se makes plain to us wh y the di stric t judge w as not convin ced the career offender gui deline
w as out of place here. See R ita , 551 U.S. at 358-59, 127 S. Ct. at 2469 (sh or t expla na t i on of court’s sentencing rat i onale suffi

ci ent whe re re c or d makes plain reason for i ts conclu si on); Jones , 798 F .3d at 618 (“So long as the recor d giv es us confi dence that the court meaningfully consi dered the defendant’s mi tigati on arg uments, ‘ev en i f i mpli ci tly and i mpreci sely ,’ that i s enough.”) (quoti ng United States v
. Diekemper, 604 F .3d 345, 355 (7th Ci r
. 2010)). R osales had not the requis i te tw o but rat her three prior convic tions for d r ug tr affi cking, and the case for those predic ates being minor (or , for that matter

, remot e from hi s present convict i on, as he has also arg ued) w as nev er as convin cing as hi s couns el made i t out to be. One of those three convic tions i nv olv e d a 7 .3-pound quanti ty of mari juana, whi ch is by no means a small quanti ty , let alone a perso na l -u se quanti ty , as Rosales has said w a s typical of hi s prior convic

tions

. Mor e to the poin t, Rosales’s cri minal hi stor y reflects a patter n o f dr ug sales that began wi th mari juana, tr ansi tioned to cocaine (a more seri ous narcotic) , and culm inated in a multi

partici pant tr affi cki ng oper ation that dealt in what the di stric t judge characterized as sub stanti al quanti ties of the latter drug. (She found that Rosales w as responsi ble for 2.87 kilograms of cocaine, conserv ativ ely .) Apart from the predic ate convic tions tr i gge ring the career offender enhanc ement, Ro sales’s cri minal hi stor y i nclu ded multipl e a rr ests and convic tions for the possess i on of narcotics and drug paraphernalia. Furt hermor e,
as the di st r ict judge poin ted out, hi s hi stor y rev ealed no evidenc e of legiti mate income in the y ears i mmedi ately precedi ng the i ns t a nt offense. So one could reasonably infer ,No. 15-1580 11
and i t is obvious to us that Judge Crabb di d, that Rosales w as engaged i n drug dealing in those y ears and that the tr ansac tions t hat gav e ris e to thi s prosecuti on w ere part of a y earslong, conti nuous, and escalating patter n of drug deal ing

. In short, i t does not appear that Rosales w as unfai rly ensnared by the career offender guid eli ne. Bey ond thi s, Ro sa l e s’s attack on the career offender gui deline w as really a challen ge to the wi sdom of the gui deline i tself, whi ch, as we hav e sai d, w as the sort of chall e ng e the di stric t courtw as not required to addr ess. III. For all of the foreg oin g re a so ns, w e AFF IRM Rosales’s sentence.