### In the 

# United States Court of Appeals For the Seventh Circuit

____________________ No. 17

- 2618
M ICHAEL D ANIELS , P etitioner

- Appellant ,

v.
U NITED S TATES OF A MERICA , Respondent

- Appellee

.

____________________ Appeal from the United States District Court for the Eastern District of Wisconsin

. No. 15

- CV

- 1440

— J.P. Stadtmueller , Judge

.

____________________ A RGUED F EBRUARY 21, 2019

— D ECIDED O CTOBER 4, 2019

____________________
Before E ASTERBROOK , S YKES , and B ARRETT , Circuit Judges

. S YKES , 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 t wo of his many prior crim e s , he was sentenced as a career offender under the then

- mandatory S entencing G uidelines . B ut t h e designation did no t a ffect his sentencing range , which was 360 months to life with or without it

.2 No. 17

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More than two decades later, Daniels mo ved to vaca te 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 a s unconstitutionally vague. Daniels argued that the identical ly phrased r esidual clause in the career

- offender g uideline is likewise unconstitutionally vague

. Because o ne of the predicate convictions for his career

- offender status qualified only under the residual clause, Daniels maintained that he was entitled to re sentencing

. The district judge d isagreed , relying

on Beckles v. United States , 137 S. Ct. 886 (2017 ) , which foreclose s vagueness challenges to the post

- Booker advisory S entencing G uidelines

. T he judge certifi ed 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, rul ing that defendants who were sentenced under the mandatory Guidelines may bring Johnson

- based vagueness challenge s to the career

- offender guideline

. C ross v. Un ited States , 892 F.3d 288, 304

– 06 (7th Cir. 2018). Applying Johnson , the panel in Cross invalidate d the residual clause of the “ crime of violence ” definition in the career

- offender g uideline and applie d that rul ing retroactively , authorizing relief under § 2255

. Id

. at 299

– 30 4

. W e directed the parties to file new briefs addressing the effect of Cross on this case

. W e now affirm. Under Johnson and Cross , Daniels was wrongly designated a career offender . B ut the error was harmless because it did not affect his sentence.No. 17

- 2618 3

I. Background
O n 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, 7 56

– 57, 778

– 79 (7th Cir. 1993 ). To briefly recap, Daniels helped t he 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 indict ment with conspiracy and related drug

- traffic king and firearms offenses . After a seven

week trial, a jury found him guilty o f 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 cocai ne, 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 u nder the then

mandatory S entencing G uidelines

. H is lengthy criminal record placed him in c riminal

- h istory c ategory V , and his offense level was 38

. T wo of his prior convicti ons

— a 1982 conviction for “ rape and indecent liberties to a child ” and a 1988 conviction for possession of a controlled substance w ith 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, Dani els was designated a career offender based on these two convictions , which raised his criminal

history category to VI . But th e designation had no effect on the sentencing range. With an offense level of 38 and a4 No. 17

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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. Unit ed States , 516 U.S. 137 (1995), ca st 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 leve l 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. A s before , the

career

- offender designation had no effect: The sentencing range was 360 months to life with or without it

. The judge

re imposed the same 420

- month sentence for the two remaining convictions, explaining that he saw no reason to revisi t the original sentenc e

. Daniels unsuccessfully appealed th e 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 th at motion was pending, Daniels wrote to the U .S. Probation Office asking i t to review his career

- offender label

. On review t he Probation O ffice determined that Da niels was not in fact a career offender because the 1988 drug c onviction 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

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none of h is other convictions qualified as career

- offender predicate s

. On February 9, 2009, t he P robation O ffice sent a letter to the Bureau of Prisons remov ing the career

- offender designation to ensure that the original misdesignation would n o t affect Daniels ’ s security classification. T he letter also explained that eliminating the career

- offender label did not change Daniels ’ s Guidelines sentencing range , which remained 360 months to life

. The ju dge 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 no t 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 S entencing G uidelines for certain drug offenses. He reminded the court that he was no longer a career offende r. The P robation O ffice reduc ed Daniels ’ s offense level in light of the amendment but advised the judge that the change did not affect the G uideline s range and therefore no adjustment in the sentence was warranted. The judge agreed and denied the motion.
Later in 2015 Daniels filed th e present § 2255 motion . He again challeng ed his career

- offender designation , only this time he invok ed the Supreme Court ’ s decision in Johnson , which invalidate d the residual clause in the Armed Career Criminal Act on vagueness grounds

. 135 S. Ct. at 2563. Daniels argue d that the identically worded residual clause in the career

- offender guideline is likewise unconstitutionally vague

. His 1982 co nviction for sexual abus e of a minor had6 No. 17

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been counted as a crime of violence only under the residual clause, so i n light of Johnso n , Daniels had yet another reason to attack the career

- offender designation. 2
T he district court stayed the motion to await further legal development s

— n otably, 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 G uidelines. Beckles , 137 S. Ct. at 895. Beckles did n o t , however, address whether offenders who were sentenced under the mandatory G uidelines may raise vagueness challenge s

. Id. at 892. After Beckles , the judge lifted the stay and surveyed our pre

- Beckles c ircuit 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. Tich e nor , 683 F.3d 358 (7th Cir. 2012) ; and United States v. Brierton , 165 F.3d 1133 (7th Cir. 1999). B riefl y 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 sentenc e 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 agree s 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 b ased on the Supreme Court ’ s intervening decision in Peugh v. United States , 569 U.S. 530 (2013)

. Hurlburt , 835 F.3d at 722

– 25. B eckles clearly displaced Hurlburt , but the status of earlier circuit caselaw remained unclear. T he 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

- off ender status. O n November 14, 2018, t he P robation O ffice again wrote to the Bureau of Prisons noting the mistake n career

- offender designation and explaining that the misdesignation did no t a ffect Daniels ’ s G uidelines 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 init ial brief s but before oral argument , another panel of this court address ed 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. T he mandatory Guidelines, Cross explained, are meaningfully different and may be challenged on vagueness grounds

. Id. Applying the logic of Johnson , the Cross panel invalidate d the residual clause in the career

- offender guideline and applied that

r ul ing 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 , w e struck the parties ’ brief s and instructed the m to file new b rief s addressing its effect on this

case. II. Discussion This § 2255 appeal presents only legal issue s , so our review is de novo. Hrobowski v. United States , 904 F.3d 566, 569 (7th Cir. 201 8 ). As we ’ ve explained, Daniels was sentenced as a career offender base d on a 1988 d rug conviction and a 1982 conviction for sexual abuse of a minor. The former was counted as a “ controlled substance offense ” for career

offender purposes . U.S.S.G. § 4B1.2(b). T he latter was considered a career

- offender predicate under the res idual 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 P robation O ffice uncovered and corrected the career

- offender misdesignation long ago

. I n 2009 the Probation Office determined that the 1988 drug conviction was f or simple f elony p ossession 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 sentencingrange, 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

. T he government has not raise d 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 t h e 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 rul ing retroactively, authorizing relief under § 2255. 892 F.3d at 299

– 30 7

. Beckles was n ’ t an obstacle in Cross b ecau se it only address e d the post

- Booker advisory G uidelines. 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 th e 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 i dentified on collateral review under 28 U.S.C. § 2254

. U nder 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) ( quotat ion marks omitted)

.10 No. 17

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T he 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, 8 39 (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

cons titutional error in jury instructions).
W e don ’ t need to resolve th at tension

. Th e 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. S ee , 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 mis designation did no t
a ffect the G uidelines range: with or without it, Daniels faced 360 months to life in prison

. Accordingly, n o record

- sensitive evaluation of the type descri bed in either Chapman or Brecht is ne eded

. Daniels identifies several cases where we examined the judge ’ s sentencing remarks to determine harmlessness even though the G uidelines range was the same with or without

3 See United States v. Smith , 723 F.3d 510, 517 (4t h 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

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the error

. See Lomax , 816 F.3d at 479; Unit ed 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 theappropriate 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 t his was unexplained dicta . Even so , it merely suggests that if the judge had explicitly t ied the sentence to the career

- offender misdesignation, t h e error would have be en harmful

. Here the judge never mention ed t h e career

- offender designation in announcing his sentencing decision

. No further inquiry is required.
Nor does Narvaez v. United States help Daniels ’ s position. There t he § 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. Th e career

- offender designation “ increased the then

mandatory sentencing range

... from 100

– 1 25 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, ” t he petitioner moved to vacate his sentence under § 2255

. We reversed the district court ’ s denial of relief, holding that t he petitioner “ never should have been classified as a career offender and never should have been s ubject ed to the enhanced punishment. ” Id. at 627. Daniels compares his circumstances to Narvaez but overlooks a crucial distinction : In that case the career

offender mis designation increased the G uidelines range

. Not so here.12 No. 17

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Finally, Daniels argues that th e career

- offender mis designation carries prejudicial collateral consequences. He lists three: T he Bureau of Prison ’ s security

- classification rules account for an inmate ’ s criminal

- history category , the G uidelines rules on supervised release similarly con sider 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 P robation O ffice addressed any possible collateral effects of the misdesignation in two separate lette rs to the Bureau of Prisons. Its 2009 letter explain ed that Daniels is not in fact a career offender , ensuring that the initial misdesignation will not affect his security classification. I n the 2018 letter , the Probation Office explain ed that the initial mis designation “ 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 wa s harmles s because it did not affect the Guidelines range. T he district judge properly denied the § 2255 motion. A FFIRMED