In the

United States Court of Appeals

For the Seventh Circuit ____________________

No. 17-2618

MICHAEL DANIELS,

Petitioner-Appellant,

v.

UNITED STATES OF AMERICA,

Respondent-Appellee.

____________________

Appeal from the United States District Court

for the Eastern District of Wisconsin.

No. 15-CV-1440 — J.P. Stadtmueller, Judge.

____________________

ARGUED FEBRUARY 21, 2019 — DECIDED OCTOBER 4, 2019

____________________

Before EASTERBROOK, SYKES, and BARRETT, Circuit Judges.

SYKES, Circuit Judge. In 1991 Michael Daniels was sentenced to 35 years in prison for drug-trafficking crimes he 

committed while leading the violent Brothers of the Struggle 

street gang in Milwaukee in the 1980s. Based on two of his 

many prior crimes, he was sentenced as a career offender 

under the then-mandatory Sentencing Guidelines. But the

designation did not affect his sentencing range, which was

360 months to life with or without it.
2 No. 17-2618

More than two decades later, Daniels moved to vacate his 

sentence under 28 U.S.C. § 2255 on the authority of Johnson v. 

United States, 135 S. Ct. 2551 (2015), which invalidated the 

“residual clause” in the Armed Career Criminal Act as 

unconstitutionally vague. Daniels argued that the identically 

phrased residual clause in the career-offender guideline is 

likewise unconstitutionally vague. Because one of the predicate convictions for his career-offender status qualified only 

under the residual clause, Daniels maintained that he was 

entitled to resentencing. The district judge disagreed, relying 

on Beckles v. United States, 137 S. Ct. 886 (2017), which forecloses vagueness challenges to the post-Booker advisory 

Sentencing Guidelines. The judge certified his decision for 

appeal based on uncertainty about the status of circuit 

precedent regarding vagueness challenges to the pre-Booker 

mandatory Guidelines.

The parties addressed that question in their initial briefs. 

In the meantime, a panel of this court issued a definitive 

answer, ruling that defendants who were sentenced under 

the mandatory Guidelines may bring Johnson-based vagueness challenges to the career-offender guideline. Cross v. 

United States, 892 F.3d 288, 304–06 (7th Cir. 2018). Applying 

Johnson, the panel in Cross invalidated the residual clause of 

the “crime of violence” definition in the career-offender 

guideline and applied that ruling retroactively, authorizing 

relief under § 2255. Id. at 299–304.

We directed the parties to file new briefs addressing the 

effect of Cross on this case. We now affirm. Under Johnson

and Cross, Daniels was wrongly designated a career offender. But the error was harmless because it did not affect his 

sentence.
No. 17-2618 3

I. Background

On direct appeal 26 years ago, we described Daniels’s extensive involvement with a violent drug-trafficking organization in Milwaukee in the 1980s. See United States v. Goines, 

988 F.2d 750, 756–57, 778–79 (7th Cir. 1993). To briefly recap,

Daniels helped the Brothers of the Struggle gain a foothold 

in the city, ran one of the gang’s drug houses, recruited 

others to join the conspiracy, and generally “ruled with the 

proverbial iron fist through intimidation.” Id. at 779.

Daniels and 14 coconspirators were arrested in 1990 and 

charged in a 36-count indictment with conspiracy and 

related drug-trafficking and firearms offenses. After a sevenweek trial, a jury found him guilty of three crimes: (1) conspiracy to possess cocaine with intent to distribute, 21 U.S.C. 

§§ 841(a)(1), 846; (2) using a communication facility to 

further the distribution of cocaine, id. § 843(b); and (3) using 

a firearm in relation to a drug-trafficking crime, 18 U.S.C.

§ 924(c). He was sentenced in 1991 under the thenmandatory Sentencing Guidelines. His lengthy criminal 

record placed him in criminal-history category V, and his 

offense level was 38. Two of his prior convictions—a 1982 

conviction for “rape and indecent liberties to a child” and a

1988 conviction for possession of a controlled substance with 

intent to distribute—qualified as a “crime of violence” and a 

“controlled substance offense,” respectively, and thus counted as the two predicates necessary to trigger application of 

the career-offender guideline. U.S.S.G. § 4B1.1–.2.

Accordingly, Daniels was designated a career offender

based on these two convictions, which raised his criminalhistory category to VI. But the designation had no effect on

the sentencing range. With an offense level of 38 and a 
4 No. 17-2618

criminal-history category of either V or VI, the range was the 

same: 360 months to life. The judge imposed concurrent 

sentences of 420 months for the two drug crimes and a 

consecutive sentence of 60 months for the firearm offense. 

A few years later, the Supreme Court’s decision in Bailey 

v. United States, 516 U.S. 137 (1995), cast doubt on the § 924(c) 

conviction, and Daniels filed a § 2255 motion to vacate his 

sentence. The judge granted the motion, vacated the firearm

conviction, and resentenced him on the two remaining 

counts. His offense level increased to 40 because he became 

eligible for a firearm-related enhancement that was previously precluded by the separate § 924(c) conviction. His

criminal-history category remained the same. As before, the 

career-offender designation had no effect: The sentencing

range was 360 months to life with or without it. The judge 

reimposed the same 420-month sentence for the two remaining convictions, explaining that he saw no reason to revisit

the original sentence.

Daniels unsuccessfully appealed the judge’s resentencing

decision and thereafter filed a flurry of motions challenging 

other aspects of his sentence. One such motion attacked the 

career-offender designation. While that motion was pending, 

Daniels wrote to the U.S. Probation Office asking it to review

his career-offender label. On review the Probation Office 

determined that Daniels was not in fact a career offender 

because the 1988 drug conviction was for simple felony drug 

possession, not possession with intent to distribute,1 and 

 1 The original charge was for possession of controlled substances with 

intent to distribute.
No. 17-2618 5

none of his other convictions qualified as career-offender

predicates.

On February 9, 2009, the Probation Office sent a letter to 

the Bureau of Prisons removing the career-offender designation to ensure that the original misdesignation would not 

affect Daniels’s security classification. The letter also explained that eliminating the career-offender label did not 

change Daniels’s Guidelines sentencing range, which remained 360 months to life. The judge reviewed the letter and 

acknowledged that “one of [Daniels’s] prior felony convictions was erroneously found to be a ‘controlled substance 

offense’ as defined in § 4B1.2, when it in fact did not meet 

the definition.” Because the Guidelines range did not 

change, the judge took no further action.

In 2015 Daniels moved to reduce his sentence under 

18 U.S.C. § 3582(c)(2) based on a retroactive amendment to 

the Sentencing Guidelines for certain drug offenses. He

reminded the court that he was no longer a career offender. 

The Probation Office reduced Daniels’s offense level in light 

of the amendment but advised the judge that the change did 

not affect the Guidelines range and therefore no adjustment 

in the sentence was warranted. The judge agreed and denied

the motion. 

Later in 2015 Daniels filed the present § 2255 motion. He 

again challenged his career-offender designation, only this 

time he invoked the Supreme Court’s decision in Johnson, 

which invalidated the residual clause in the Armed Career 

Criminal Act on vagueness grounds. 135 S. Ct. at 2563.

Daniels argued that the identically worded residual clause in 

the career-offender guideline is likewise unconstitutionally 

vague. His 1982 conviction for sexual abuse of a minor had 
6 No. 17-2618

been counted as a crime of violence only under the residual

clause, so in light of Johnson, Daniels had yet another reason 

to attack the career-offender designation.2

The district court stayed the motion to await further legal 

developments—notably, the Supreme Court’s decision in 

Beckles, which rejected a Johnson-based vagueness challenge 

to the residual clause of the career-offender guideline in the

post-Booker advisory Guidelines. Beckles, 137 S. Ct. at 895. 

Beckles did not, however, address whether offenders who 

were sentenced under the mandatory Guidelines may raise 

vagueness challenges. Id. at 892.

After Beckles, the judge lifted the stay and surveyed our

pre-Beckles circuit precedent on vagueness challenges to the 

Sentencing Guidelines, including United States v. Hurlburt, 

835 F.3d 715 (7th Cir. 2016) (en banc); United States v. Tichenor, 683 F.3d 358 (7th Cir. 2012); and United States v. Brierton, 

165 F.3d 1133 (7th Cir. 1999). Briefly stated, in Brierton we 

ruled that the mandatory Guidelines cannot be challenged 

on vagueness grounds, 165 F.3d at 1139, and Tichenor extended that holding to the post-Booker advisory Guidelines,

 

2 As we’ve noted, over the years Daniels filed multiple requests for relief 

from his sentence. Other than the Bailey challenge to the § 924(c) conviction, none were captioned as a § 2255 motion. Under Magwood v. 

Patterson, 705 U.S. 320 (2010), and Suggs v. United States, 705 F.3d 279, 282 

(7th Cir. 2013), the sentence imposed after Daniels successfully challenged his § 924(c) conviction is deemed a new judgment for § 2255 

purposes. Based on his many other requests for relief, however, the 

present § 2255 motion might constitute a successive petition requiring 

authorization. See 28 U.S.C. § 2255(h). Based on the “convoluted procedural history” of the case and the substantive changes in the law, the 

government agrees that it should not be so construed. We accept that

concession. 
No. 17-2618 7

683 F.3d at 364–65. But we overruled Tichenor in Hurlburt

based on the Supreme Court’s intervening decision in Peugh 

v. United States, 569 U.S. 530 (2013). Hurlburt, 835 F.3d at 722–

25. Beckles clearly displaced Hurlburt, but the status of earlier

circuit caselaw remained unclear. The judge denied the 

§ 2255 motion but granted a certificate of appealability, 

noting the “analytical minefield” in our caselaw after Beckles.

This appeal followed. While briefing was underway, 

Daniels submitted additional pro se filings to the district 

court concerning his career-offender status. On November 14, 2018, the Probation Office again wrote to the Bureau 

of Prisons noting the mistaken career-offender designation

and explaining that the misdesignation did not affect Daniels’s Guidelines range and “will not impact the terms or 

conditions of his supervised release.” The Probation Office 

also explained that if Daniels ever faces a future revocation 

proceeding, a criminal-history category V will be used “in 

any [Guidelines] calculations.”

After the parties filed their initial briefs but before oral 

argument, another panel of this court addressed the “analytical minefield” that troubled the district judge, ruling that

the Supreme Court’s holding in Beckles is limited to the 

advisory Guidelines. Cross, 892 F.3d at 304–07. The mandatory Guidelines, Cross explained, are meaningfully different 

and may be challenged on vagueness grounds. Id. Applying

the logic of Johnson, the Cross panel invalidated the residual 

clause in the career-offender guideline and applied that 

ruling retroactively to authorize § 2255 relief for two defendants who were sentenced as career offenders under the 

mandatory Guidelines. Id. at 307.
8 No. 17-2618

In light of Cross, we struck the parties’ briefs and instructed them to file new briefs addressing its effect on this

case.

II. Discussion

This § 2255 appeal presents only legal issues, so our review is de novo. Hrobowski v. United States, 904 F.3d 566, 569

(7th Cir. 2018). As we’ve explained, Daniels was sentenced as 

a career offender based on a 1988 drug conviction and a 1982 

conviction for sexual abuse of a minor. The former was 

counted as a “controlled substance offense” for careeroffender purposes. U.S.S.G. § 4B1.2(b). The latter was considered a career-offender predicate under the residual clause 

of the definition of “crime of violence.” Id. § 4B1.2(a)(2). For 

years Daniels has argued that neither conviction actually 

qualifies, making the career-offender label erroneous. 

We begin with the obvious: The Probation Office uncovered and corrected the career-offender misdesignation long 

ago. In 2009 the Probation Office determined that the 1988 

drug conviction was for simple felony possession of controlled substances, which doesn’t qualify as a predicate 

controlled-substance offense. That knocked out one of the 

two necessary predicates for the career-offender designation, 

and although the error had no effect on Daniels’s sentencing 

range, the Probation Office took steps to correct the misdesignation with the Bureau of Prisons.

After Cross, it’s now clear that the 1982 conviction also 

should not have been counted. The government has not 

raised a timeliness objection to this new claim: Daniels filed 

his § 2255 motion within one year of the Supreme Court’s 

decision in Johnson, as required by 28 U.S.C. § 2255(f)(3). 
No. 17-2618 9

And the claim is clearly cognizable under Cross. The 1982 

conviction for sexual abuse of a minor was included as a 

career-offender predicate only under the residual clause of 

the “crime of violence” definition in the Guidelines. U.S.S.G.

§ 4B1.2(a)(2). Cross invalidated the residual clause as unconstitutionally vague in light of Johnson and applied that ruling 

retroactively, authorizing relief under § 2255. 892 F.3d at 

299–307. Beckles wasn’t an obstacle in Cross because it only 

addressed the post-Booker advisory Guidelines. See id. at 304. 

Other circuits disagree, but Cross controls and Beckles is not 

an obstacle here either. See D’Antoni v. United States, 916 F.3d 

658, 664 n.4 (7th Cir. 2019) (collecting cases from other 

circuits).

All this is undisputed. Everyone agrees that Daniels was 

mistakenly designated a career offender based on two 

nonqualifying predicates. “Since the parties do not dispute 

the error, we [need] only address whether the error [is]

harmless.” United States v. Lomax, 816 F.3d 468, 478 (7th Cir. 

2016). 

The parties debate whether the Chapman or Brecht standard governs the harmless-error analysis. The former applies 

to constitutional errors identified and reviewed on direct 

appeal and requires the government to demonstrate that the

error “was harmless beyond a reasonable doubt.” Chapman 

v. California, 386 U.S. 18, 24 (1967). The latter applies to 

constitutional errors identified on collateral review under 

28 U.S.C. § 2254. Under Brecht v. Abrahamson, a state prisoner

must show that the error “had [a] substantial and injurious 

effect or influence in determining the jury’s verdict.”

507 U.S. 619, 623, 633–34 (1993) (quotation marks omitted).
10 No. 17-2618

The Supreme Court has not addressed which standard 

applies in § 2255 cases, but some of our sister circuits have 

adopted Brecht in this context.3 We haven’t taken a firm 

position, and our caselaw gestures in conflicting directions. 

Compare Lanier v. United States, 220 F.3d 833, 839 (7th Cir. 

2000) (applying a harmless-error test resembling the 

Chapman formulation), with Sorich v. United States, 709 F.3d 

670, 674 (7th Cir. 2013) (using the Brecht standard to evaluate

constitutional error in jury instructions).

We don’t need to resolve that tension. The error here is 

harmless under any standard. We have long held that 

Guidelines-calculation errors that don’t affect a defendant’s 

sentencing range are harmless as a matter of law. See, e.g.,

United States v. Harmon, 721 F.3d 877, 892 (7th Cir. 2013) 

(concluding that any error in calculating a defendant’s 

criminal-history category “was harmless” because “his 

guidelines range was the same—360 months to life—

whether he was in criminal history category I or II”). It’s 

undisputed that the career-offender misdesignation did not

affect the Guidelines range: with or without it, Daniels faced 

360 months to life in prison. Accordingly, no record-sensitive 

evaluation of the type described in either Chapman or Brecht

is needed.

Daniels identifies several cases where we examined the 

judge’s sentencing remarks to determine harmlessness even 

though the Guidelines range was the same with or without 

 3 See United States v. Smith, 723 F.3d 510, 517 (4th Cir. 2013); United States 

v. Dago, 441 F.3d 1238, 1246 (10th Cir. 2006); United States v. Montalvo, 

331 F.3d 1052, 1058 (9th Cir. 2003) (per curiam); Ross v. United States, 

289 F.3d 677, 682 (11th Cir. 2002); Murr v. United States, 200 F.3d 895, 906 

(6th Cir. 2000). 
No. 17-2618 11

the error. See Lomax, 816 F.3d at 479; United States v. Anderson, 517 F.3d 953, 966 (7th Cir. 2008). For example, he points 

to language from Lomax stressing that “had the district court 

relied on [the] career offender status when choosing the 

appropriate sentence, the error would not have been harmless even though the guideline range would have been the 

same.” 816 F.3d at 479. We note for starters that this was 

unexplained dicta. Even so, it merely suggests that if the 

judge had explicitly tied the sentence to the career-offender 

misdesignation, the error would have been harmful. Here

the judge never mentioned the career-offender designation 

in announcing his sentencing decision. No further inquiry is 

required.

Nor does Narvaez v. United States help Daniels’s position.

There the § 2255 petitioner pleaded guilty to bank robbery 

and was sentenced as a career offender based on two prior 

Wisconsin convictions for failing to return to confinement. 

The career-offender designation “increased the thenmandatory sentencing range ... from 100–125 months to 

151–188 months,” and the judge imposed a prison term at 

the midpoint of the enhanced Guidelines range. Narvaez v. 

United States, 674 F.3d 621, 624 (7th Cir. 2011). After the 

Supreme Court cast doubt on whether his prior convictions 

qualified as “crimes of violence,” the petitioner moved to 

vacate his sentence under § 2255. We reversed the district 

court’s denial of relief, holding that the petitioner “never 

should have been classified as a career offender and never 

should have been subjected to the enhanced punishment.” 

Id. at 627. Daniels compares his circumstances to Narvaez but 

overlooks a crucial distinction: In that case the careeroffender misdesignation increased the Guidelines range. Not 

so here.
12 No. 17-2618

Finally, Daniels argues that the career-offender misdesignation carries prejudicial collateral consequences. He lists 

three: The Bureau of Prison’s security-classification rules 

account for an inmate’s criminal-history category, the Guidelines rules on supervised release similarly consider a defendant’s criminal-history category, and future changes in 

the law that might otherwise benefit him may not apply to 

career offenders. 

But the Probation Office addressed any possible collateral 

effects of the misdesignation in two separate letters to the 

Bureau of Prisons. Its 2009 letter explained that Daniels is 

not in fact a career offender, ensuring that the initial misdesignation will not affect his security classification. In the 2018 

letter, the Probation Office explained that the initial misdesignation “will not impact the terms of conditions of his 

supervised release” and that the correct criminal-history 

category will be used in any Guidelines calculations “if 

Mr. Daniels face[s] future revocation proceedings.”

In short, although Daniels was wrongly designated a career offender, the error was harmless because it did not 

affect the Guidelines range. The district judge properly 

denied the § 2255 motion. 

AFFIRMED