The Honorable Joseph Van Bokkelen, United States District Court Judge for the *

Northern District of Indiana, sitting by designation.

United States Court of Appeals

For the Seventh Circuit

Chicago, Illinois 60604

Argued May 14, 2009

Decided August 4, 2009

Before

 ILANA DIAMOND ROVNER, Circuit Judge

 TERENCE T. EVANS, Circuit Judge

 JOSEPH VAN BOKKELEN, District Judge

*

No. 08-4238

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

DEMARKO STEWARD,

 Defendant-Appellant.

Appeal from the United States District

Court for the Southern District of Illinois.

No. 08 CR 30060

J. Phil Gilbert,

Judge.

ORDER

Demarko Steward, a small-time drug trafficker, was sentenced to a term of 200

months after the district court concluded that he was a career offender under the

sentencing guidelines. Steward appeals his sentence by mounting, as he did before the

district court, a sweeping attack on the use of the career offender enhancement on low-level

NONPRECEDENTIAL DISPOSITION

To be cited only in accordance with

Fed. R. App. P. 32.1
No. 08-4238 Page 2

drug dealers like himself and arguing that the court accorded the enhancement undue weight.

In 2005, the police set up three controlled buys through a confidential informant and

an undercover officer over a four-month period, with Steward as their target. The buys

were a success--Steward sold 11.5 grams of crack cocaine and 1.2 grams of cocaine. On one

occasion he also brokered the sale of an inoperable handgun. Steward received the gun in a

cocaine deal and then immediately resold it to the informant for $80. Two years later

Steward was indicted for distributing crack cocaine (two counts), distributing cocaine, and

being a felon in possession of a firearm. See 21 U.S.C. § 841(a)(1); 18 U.S.C. § 922(g)(1). He

pleaded guilty to all counts.

A probation officer prepared a presentence report, noting that Steward was a career

offender since he had three prior state convictions for possession with intent to deliver

either cocaine or marijuana. U.S.S.G. § 4B1.1. But like the charged conduct, these prior

drug trafficking convictions showed that he was no large-scale distributor. In total

(combining all three convictions), Steward was caught with less than 6 grams of cocaine

and less than 25 grams of marijuana. Based on the career offender enhancement, the

probation officer calculated Steward’s guidelines range to be 188 to 235 months of

imprisonment. Were he not a career offender, the range would have been 100 to 125

months of incarceration.

Steward objected to the PSR, arguing that the career offender enhancement, for lowlevel retail traffickers, was fatally flawed. He contended that at its inception the

enhancement, like the 100-1 crack to powder cocaine sentencing ratio, lacked empirical

support and cited a Sentencing Commission report questioning its use in cases like his. 

U.S. SENTENCING COMM’N, FIFTEEN YEARS OF GUIDELINES SENTENCING: AN ASSESSMENT OF

HOW WELL THE FEDERAL CRIMINAL JUSTICE SYSTEM IS ACHIEVING THE GOALS OF SENTENCING

REFORM 133-34 (2004). The government responded by pointing out that the enhancement

technically applied--a fact that Steward did not dispute--and that the court had an

obligation to accurately calculate the guidelines range before imposing Steward’s sentence. 

In its view, Steward’s contention was merely a “sentencing argument masquerading as a

PSR objection.” Steward, however, also made a straightforward sentencing argument in a

separate statement of mitigating factors. There, he argued that the enhancement’s

application resulted in a sentence greater than necessary, in contravention to the sentencing

factors listed in 18 U.S.C. § 3553(a). He reiterated his attack on the career offender

guidelines but also pointed to his tough childhood, which included abuse at the hands of

alcoholic parents and stints in foster care, as well as his active pursuit of drug treatment. 

Ultimately, he argued for a sentence of 100 months, the bottom of his unenhanced

guidelines range.
No. 08-4238 Page 3

At sentencing the district court first dealt with Steward’s objections to the PSR. 

Noting that he fell within the ambit of the career offender enhancement, the court agreed

with the probation officer and the government and set the guidelines range at 188 to 235

months. In reaching this decision, the court stated that “if the career offender status under

the guidelines, the law, is going to be changed, it’s not going to [be] by this Court.” It then

proclaimed that it had “considered all the information in the presentence report including

guideline computations and factors set forth in 18 U.S.C. § 3553(a)” and sentenced Steward

to 200 months. The court provided no further analysis of the statutory sentencing factors,

nor did it mention any of Steward’s arguments under those factors.

On appeal Steward renews his wholesale attack on the career offender guidelines. A

district court’s duties at sentencing are twofold: first, the court must correctly calculate the

applicable guidelines range; secondly, it must make an individualized assessment of the

defendant, in light of the sentencing factors listed in 18 U.S.C. § 3553(a), to arrive at a

reasonable sentence and adequately explain the chosen sentence to allow for meaningful

review. Gall v. United States, 128 S. Ct. 586, 596-97 (2007). Because Steward seems to argue

that the career offender guidelines are so flawed that they should have been ignored at

both steps, we turn to the district court’s execution of this two-step process.

As an initial matter, the court correctly applied the enhancement when calculating

the guidelines range. Steward admits that he technically fits under the career offender

guideline, and the district court was not free to ignore this fact--it is well-settled (as we’ve

just noted) that the district court’s first obligation is to correctly calculate the defendant’s

guidelines range, as they stand. Gall, 128 S. Ct. at 596; United States v. Sachsenmaier, 491 F.3d

680, 685 (7th Cir. 2007). The court’s statement that the career offender status enhancement

is “the law” was not, as Steward argues on appeal, a revelation of its mistaken belief that

the guidelines were mandatory. In fact, during both the sentencing hearing and the change

of plea hearing, the court explicitly recognized that they are advisory. Rather, the

statement merely reaffirms the court’s obligation to accurately calculate the guidelines

range during the sentencing hearing.

But the court’s duties do not end after the guidelines are calculated. The guidelines

provide insight for fashioning an appropriate sentence, but the punishment must

ultimately be based on § 3553(a) “without any thumb on the scale favoring a guideline

sentence.” Sachsenmaier, 491 F.3d at 685; see also Nelson v. United States, 129 S. Ct. 890, 892

(2009). Steward not only attacked the guidelines calculation, but he also maintained that

the calculation yielded a punishment greater than necessary, contravening § 3553(a). 

Steward renews this argument on appeal, and so we must review his sentence for an abuse
No. 08-4238 Page 4

of discretion, remanding for resentencing only if the district court failed to consider the

statutory factors or failed to adequately explain the chosen sentence. Gall, 128 S. Ct. at 597.

On this record, we reluctantly find an abuse of discretion. The court’s entire §

3553(a) analysis consists of a fragment of a sentence, where it mentions in passing that it

considered the statutory factors. True, a court need not belabor its analysis, United States v.

Dean, 414 F.3d 725, 729 (7th Cir. 2005), but it must explain its decision adequately enough to

allow for appellate review, United States v. Cunningham, 429 F.3d 673, 679 (7th Cir. 2005) (“A

rote statement that the judge considered all relevant factors will not always suffice; the

temptation to a busy judge to impose the guidelines sentence and be done with it, without

wading into the vague and prolix statutory factors, cannot be ignored.”). And while a

district court is free to gloss over insubstantial arguments, ignoring a defendant’s principal

contention is not wise.

Here, Steward presented unrebutted evidence that he was a small-time drug dealer. 

His prior distribution convictions--the crimes that made him a career offender--involved, in

total, around a shot glass full of illegal substances. Steward also pointed to the Sentencing

Commission’s own report, questioning the efficacy of using drug trafficking convictions,

especially for retail-level traffickers, to qualify a defendant for career offender status. U.S.

SENTENCING COMM’N, supra, at 133-34. The Commission noted that the goal of

incapacitating criminals was undermined since, unlike repeat violent offenders (who also

qualify as career offenders), retail-level drug traffickers are readily replaced. Likewise,

preliminary research suggests that the recividism rates for drug traffickers sentenced as

career offenders are much lower than other offenders who are similarly assigned to a

criminal history category VI. And on top of this generalized evidence, the PSR notes that

Steward, who was receiving drug treatment, was not only compliant, but that he spent

extra time trying to get straight. According to his health care providers, he seemed “very

sincere in his efforts to change his life and be a better father.”

These facts add up to a nonfrivolous argument for a sentence at the low end, or even

below, the guidelines range. After United States v. Booker, 543 U.S. 220 (2005), the district

court is free to, in fact required to, look beyond a defendant’s career offender status, to his

individual situation to determine a reasonable sentence under § 3553. See United States v.

Liddell, 543 F.3d 877, 884-85 (7th Cir. 2008) (holding that all of the sentencing guidelines,

including the career offender enhancement, are advisory); United States v. Harris, 536 F.3d

798, 813 (7th Cir. 2008) (same). That statute requires the district court to “impose a

sentence sufficient, but not greater than necessary,” taking into account (among other

things) the defendant’s history and the need to protect the public from further crimes of the

defendant. See id. at (a)(1), (a)(2)(C). Steward’s well-supported plea for a 100-month
No. 08-4238 Page 5

sentence focused on these two factors, but the court passed over his request in silence. By

doing so we cannot be sure that the court exercised its discretion (that is, even considered

the factors relevant to sentencing raised by Steward), let alone whether it abused its

discretion in doing so. This shortcoming precludes affirming Steward’s sentence.

Of course, reasonableness is a range, not a point, and we recognize that the sentence

imposed by the judge may, if further explained, pass muster. We express no view on the

proper sentence and hold only that the court must adequately explain its sentence under

§ 3553(a). Accordingly, the judgment of the district court is VACATED and the case is

REMANDED for resentencing.