In the

United States Court of Appeals

For the Seventh Circuit

No. 15-1580

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

ORLANDO ROSALES,

Defendant-Appellant.

Appeal from the United States District Court for the 

Western District of Wisconsin

No. 3:14-cr-00114-bbc-1 — Barbara B. Crabb, Judge.

ARGUED NOVEMBER 10, 2015 — DECIDED FEBRUARY 11, 2016

Before POSNER, EASTERBROOK, and ROVNER, Circuit Judges.

ROVNER, Circuit Judge. Orlando Rosales pleaded guilty to

a charge that he conspired to possess, with intent to distribute,

500 grams or more of cocaine, and was sentenced to a term of

120 months in prison. He appeals the sentence, contending that

the district court committed procedural error by not giving

adequate reasons for rejecting his contention that he shouldnot

be sentenced as a career offender. We affirm.
2 No. 15-1580

I.

Rosales played a managerial role in a small cocaine trafficking ring in Sauk County, Wisconsin. With the assistance of

three other individuals, Rosales obtained cocaine from two

different suppliers, one in Chicago and one in Madison,

Wisconsin, and then distributed it to his customers in Wisconsin. Rosales’s drug trafficking was exposed when individuals

cooperating with the government identified his Chicago

connection as a cocaine supplier and named Rosales as one of

the supplier’s customers. The Chicago supplier was arrested

after a confidential informant arranged a controlled purchase

of cocaine from him; he in turn confirmed that he had supplied

cocaine to Rosales on multiple occasions. Rosales was ultimately charged in a one-count information with conspiracy

with the intent to distribute in excess of 500 grams of cocaine

from August 2011 to November 2013. He pleaded guilty to that

charge pursuant to a written plea agreement in which he

agreed to waive indictment and cooperate with the government (Rosales aided the government in the prosecution of the

supplier who fingered him) and in which the government

agreed to recommend that he be given maximum credit for

acceptance of responsibility and that his sentence be reduced

in recognition of his substantial assistance to the government. 

Pursuant to the Sentencing Guidelines, Rosales faced an

advisory sentence of between 188 and 235 months. The range

would have been lower—140 to 175 months—absent a threelevel increase in his offense level resulting from the career
No. 15-1580 3

offender guideline. U.S.S.G. § 4B1.1. Generally, the career 1

offender guideline applies when the defendant (1) was at least

18 years old when he committed the instant offense; (2) the

instant offense is a felony that is either a crime of violence or a

controlled substance offense; and (3) the defendant has at least

two prior felony convictions that qualify either as a crime of

violence or a controlled substance offense. § 4B1.1(a). A

controlled substance offense is defined to include a felony

offense that, as relevant here, involves the possession of a

controlled substance with the intent to distribute. § 4B1.2(b).

The crime to which Rosales pleaded guilty in this case of

course qualifies as a controlled substance offense, and Rosales

had three such prior convictions. In 2004 and 2008, he had been

convicted of possessing, with the intent to distribute, less than

200 grams and more than 2,500 grams of marijuana, respectively; and in 2011, he had been convicted of possessing, with

the intent to distribute, between one and five grams of cocaine.

The presentence report reminded the district judge that she

had the discretion to disagree with the policy reflected in the

career offender guideline when she sentenced Rosales. R. 14 at

29 ¶ 149; R. 15 at 29 ¶ 151.

In a written memorandum filed prior to sentencing, and

again in his oral remarks at the sentencing hearing, Rosales’s

counsel asked the court, on two separate but related grounds,

to disregard the sentencing increase called for by the career

Application of the career offender guideline also dictated that Rosales be

1

assigned to the top criminal history category of VI, but the extent of his

criminal history would have placed him in category VI regardless of the

career offender designation.
4 No. 15-1580

offender guideline. The first of these was a policy-based

challenge to the career offender guideline itself, positing that

the guideline was adopted without empirical research and

careful study, and represented unsound policy to the extent it

applied not only to large-scale drug traffickers but also to

relatively low-level offenders who, like Rosales, trafficked in

drugs primarily to support their own drug habits and did not

reap large amounts of money from their drug-dealing. The

second was an as-applied challenge, which argued that the

career offender designation was inappropriate in Rosales’s

case, given that his predicate drug-trafficking convictions

involved relatively modest amounts of marijuana and cocaine;

that he had no history of violence; that his drug dealings were

driven by a need to support himself, his family, and his own

drug, alcohol, and gambling habits; that his supplier received

only a 48-month sentence; and generally that a lengthier

sentencewas inconsistent with the sentencing factors identified

in 18 U.S.C. § 3553(a). Counsel proposed that Rosales be

sentenced to a term of six years.

The district court, after hearing the parties at sentencing,

adopted the pre-sentence report, applied the career offender

guideline in determining Rosales’s advisory sentencing range,

granted the government’s motion for a multi-level downward

variance from the Guidelines range based on his substantial

assistance, and ordered Rosales to serve a sentence of 120

months in prison, to be followed by a four-year period of

supervised release. After announcing the sentence, the district

judge asked defense counsel whether he “ha[d] any specific

objections to the sentence or to the conditions [of supervised

release] that you haven’t already mentioned.” R. 36 at 27.
No. 15-1580 5

MR. MANDELL: I don’t[,] other than I don’t know

why the court applied the career

offender guideline otherthan the

prior convictionsunderthe information I provided, but – 

THE COURT: That’s a good question. I applied

the career offender guideline[ ]

because Mr. Rosales’s criminal

conduct justified the application.

MR. MANDELL: Even though the prior convictions were for relatively minor

offenses?

THE COURT: Right.

MR. MANDELL: Okay.

R. 36 at 27-28.

II.

Rosales contends that the district court erred procedurally

at his sentencing by not adequately articulating its reasons for

rejecting his argument that the career offender guideline

should not be applied in his case given the relatively minor

nature of his predicate convictions. 

A district court is required at sentencing to address the

defendant’s principal arguments in mitigation unless those

arguments are without factual foundation or are too weak to

require discussion. United States v. Cunningham, 429 F.3d 673,

679 (7th Cir. 2005). This obligation functions as a safeguard

ensuring that the district judge has not overlooked and has
6 No. 15-1580

actually considered the principal issues informing her sentencing decision. United States v. Donelli, 747 F.3d 936, 940 (7th Cir.

2014). “The requirement is based on the view that a ‘judge who

fails to mention a ground of recognized legal merit (provided

it has a factual basis) is likely to have committed an error or

oversight.’” Id. (quoting Cunningham, 429 F.3d at 679).

Frequently, a defendant’s principal argument in mitigation

takes the form of a challenge to the Guidelines themselves.

After United States v. Booker, 543 U.S. 220, 125 S. Ct. 738 (2005),

a sentencing judge has the discretion to disagree either with a

particular provision of the Sentencing Guidelines, Kimbrough

v. United States, 552 U.S. 85, 128 S. Ct. 558 (2007), or the

sentencing range that results from application of the Guidelines as a whole, Rita v. United States, 551 U.S. 338, 351,

127 S. Ct. 2456, 2465 (2007), and to impose a non-Guidelines

sentence that, in her judgment, is more consistent with the

statutory sentencing factors set out in 18 U.S.C. § 3553(a). See

United States v. Corner, 598 F.3d 411, 416 (7th Cir. 2010) (en

banc). The judge’s authority to disagree with the Guidelines

extends to the career offender guideline at issue here. See id.

The court is not obliged to address all such arguments questioning the reasonableness of Guidelines provisions. The court

may pass over in silence a blanket policy challenge like

Rosales’s argument that the career offender guideline was

poorly conceived and is overbroad. See United States v. EstradaMederos, 784 F.3d 1086, 1088 (7th Cir. 2015) (collecting cases).

But an as-applied challenge to a guideline, provided it is

grounded in the facts of the case, not frivolous, and adequately

presented to the court, is one that must be addressed. See

United States v. Schmitz, 717 F.3d 536, 542 (7th Cir. 2013)
No. 15-1580 7

(distinguishing between categorical and as-applied challenges

to guideline); see also, e.g., United States v. Morris, 775 F.3d 882,

887 (7th Cir. 2015) (vacating sentence and remanding where

district court failed to address defendant’s argument that

crack-to-powder cocaine ratio resulted in excessive sentencing

range given that most of drug quantity attributed to him

comprised counterfeit crack cocaine). 

Arguments that a sentencing court committed procedural

error of the Cunningham variety, by failing to address a defendant’s principal argument in mitigation, including challenges

to the Guidelines, have become a staple in this court. See

Donelli, 747 F.3d at 941 (citing United States v. Castaldi, 743 F.3d

589, 595 (7th Cir. 2014)). And yet it is a relatively simple matter

for a district judge to obviate such an appellate argument by

ensuring, before the close of the sentencing hearing, that she

has addressed each of the defendant’s principal arguments in

mitigation. To that end, we suggested in United States v. GarciaSegura, 717 F.3d 566, 569 (7th Cir. 2013), that the judge ask

defense counsel whether he or she is satisfied that the court has

adequately addressed the main arguments in mitigation. If

counsel replies in the affirmative, a contention on appeal that

the district court failed to address a principal argument in

mitigation would be deemed waived. Id. If counsel replies in

the negative, then that would give the court the opportunity to

make clear either why it did not view the argument as warranting discussion or why it had rejected the argument on its

merits. Id.

In this case, the district judge did not pose quite the inquiry

we suggested in Garcia-Segura when she asked if there were
8 No. 15-1580

“any specific objections” to the sentence that defense counsel

hadn’t mentioned, see Morris, 775 F.3d at 886; but nonetheless

defense counsel took the opportunity to inquire why the judge

had sentenced Rosales as a career offender. The judge in turn

remarked that she applied the career offender guideline

because she thought that Rosales’s criminal conduct justified

it, notwithstanding (at defense counsel’s prompting) that his

predicate crimes were, in counsel’s view, relatively minor.

In view of this exchange, there can be no question that the

district court considered and rejected Rosales’s principal

argument in mitigation. The court plainly understood that it

had the discretion not to sentence Rosales as a career offender,

discretion that was highlighted both in Rosales’s sentencing

memorandum and the probation officer’s presentence report.

And the district judge quite clearly indicated that she believed

it appropriate to adhere to the career offender guideline in

sentencing Rosales. The only issue is the adequacy of the

judge’s explanation. Defense counsel perhaps could have

pressed the judge to say more than she did, but having already

prompted the court for an explanation, we do not fault him for

letting the matter rest once the court indicated that it had

rejected the argument on its merits.

A court’s obligation to address a defendant’s principal

argument in mitigation does include giving reasons for why it

has rejected that argument. See Garcia-Segura, 717 F.3d at 569

(citing Cunningham, 429 F.3d at 679); see also, e.g., United States

v. Thomas, 794 F.3d 705, 713 (7th Cir.) (citing Morris, 775 F.3d at

886-88), cert. denied, 136 S. Ct. 558 (2015). In this case, the

court’s explanation that it hewed to the career offender

guideline because Rosales’s conduct justified it arguably
No. 15-1580 9

amounted to ipse dixit, in that the court did not articulate why

it viewed his conduct as supporting application of the guideline. Cf. United States v. Jones, 798 F.3d 613, 618 (7th Cir. 2015)

(although record made clear district court considered defendant’s mitigation arguments but rejected them, court did not

directly explain why it found them unpersuasive). But for two

reasons we are satisfied that any Cunningham error was

harmless. See Morris, 775 F.3d at 885 (procedural error at

sentencing is subject to harmless-error review). 

First, Rosales’s as-applied challenge to the career offender

guideline overlapped substantially with his policy argument

and would apply equally to many offenders. As his sentencing

memorandum itself posited, because the career offender

guideline comes into play whenever a defendant has two prior

convictions for a drug trafficking offense, regardless of the

drug quantity involved, the guideline will apply to countless

low-level offenders who are poor, addicted to narcotics, and

resort to trafficking to support themselves and their families,

not to mention their addictions. So vis-à-vis the purported

overbreadth of the guideline, Rosales’s case did not present a

particularly unique or compelling set of circumstances that

required discussion. To be sure, the court was obliged to

consider Rosales’s personal characteristics and history in

arriving at an appropriate sentence, irrespective of how much

he may have had in common with other low-level, repeat

distributors of narcotics who qualify as career offenders. See

§ 3553(a)(1). But the courtplainly complied with that obligation

here: it addressed Rosales’s individual circumstances, including his drug and alcohol addictions, at some length in arriving

at the sentence. R. 36 at 17-18, 21-22.
10 No. 15-1580

Second, the record otherwise makes plain to us why the

district judge was not convinced the career offender guideline

was out of place here. See Rita, 551 U.S. at 358-59, 127 S. Ct. at

2469 (short explanation of court’s sentencing rationale sufficient where recordmakes plain reason for its conclusion); Jones,

798 F.3d at 618 (“So long as the record gives us confidence that

the court meaningfully considered the defendant’s mitigation

arguments, ‘even if implicitly and imprecisely,’ that is

enough.”) (quoting United States v. Diekemper, 604 F.3d 345, 355

(7th Cir. 2010)). Rosales had not the requisite two but rather

three prior convictions for drug trafficking, and the case for

those predicates being minor (or, for that matter, remote from

his present conviction, as he has also argued) was never as

convincing as his counsel made it out to be. One of those three

convictions involveda 7.3-pound quantity of marijuana, which

is by no means a small quantity, let alone a personal-use

quantity, as Rosales has said was typical of his prior convictions. More to the point, Rosales’s criminal history reflects a

pattern of drug sales that began with marijuana, transitioned

to cocaine (a more serious narcotic), and culminated in a multiparticipant trafficking operation that dealt in what the district

judge characterized as substantial quantities of the latter drug.

(She found that Rosales was responsible for 2.87 kilograms of

cocaine, conservatively.) Apart from the predicate convictions

triggering the career offender enhancement, Rosales’s criminal

history included multiple arrests and convictions for the

possession of narcotics and drug paraphernalia. Furthermore,

as the district judge pointed out, his history revealed no

evidence of legitimate income in the years immediately

preceding the instant offense. So one could reasonably infer,
No. 15-1580 11

and it is obvious to us that Judge Crabb did, that Rosales was

engaged in drug dealing in those years and that the transactions that gave rise to this prosecution were part of a yearslong, continuous, and escalating pattern of drug dealing. In

short, it does not appear that Rosales was unfairly ensnared by

the career offender guideline.

Beyond this, Rosales’s attack on the career offender

guideline was really a challenge to the wisdom of the guideline

itself, which, as we have said, was the sort of challenge the

district court was not required to address.

III.

For all of the foregoing reasons, we AFFIRM Rosales’s

sentence.