In the

United States Court of Appeals

For the Seventh Circuit ____________________

No. 17-3476

TRACY D. SHIPMAN,

Petitioner-Appellant,

v.

UNITED STATES OF AMERICA,

Respondent-Appellee.

____________________

Appeal from the United States District Court for the

Northern District of Illinois, Western Division.

No. 16 C 50016 — Philip G. Reinhard, Judge.

____________________

ARGUED FEBRUARY 22, 2019 — DECIDED JUNE 5, 2019

____________________

Before RIPPLE, MANION, and BRENNAN, Circuit Judges.

BRENNAN, Circuit Judge. Tracy Shipman appeals the district court’s denial of his petition for collateral postconviction

relief under 28 U.S.C. § 2255. When Shipman pleaded guilty 

to drug charges in 2003, the district court sentenced him under the then-mandatory Sentencing Guidelines. Because Shipman had three prior “crime of violence” felony convictions, 

the district court sentenced him as a “career offender.”
2 No. 17-3476

U.S.S.G. § 4B1.1 (2002).1 The career-offender provision of the 

Guidelines defined a “crime of violence” in U.S.S.G. 

§ 4B1.2(a)(1)–(2). Two passages in that guideline are at issue 

here: the enumerated-offenses clause, and the residual clause.

On appeal, Shipman argues the Guidelines’ residual 

clause is unconstitutionally vague. We agree, a conclusion 

that follows directly from our decision in Cross v. United 

States, 892 F.3d 288 (7th Cir. 2018). Indeed, Cross abrogated the 

rationale supporting the district court’s dismissal of 

Shipman’s petition for collateral relief. With that issue resolved, the case hits a snag: the record does not conclusively 

show whether Shipman was sentenced under the residual 

clause or the enumerated-offenses clause. We therefore remand this case for further proceedings on the merits of Shipman’s § 2255 petition.

I. BACKGROUND

Because Cross was decided nearly seven months after the 

district court issued its dismissal order, we summarize the 

facts and proceedings in this case only to the extent necessary 

to address the issues presented on appeal.2

Shipman pleaded guilty in 2003 to conspiring to manufacture and distribute methamphetamine in violation of

21 U.S.C. § 846 (2000). His presentence report used the 2002 

Sentencing Guidelines Manual, which at that time required 

 

1 Unless otherwise noted, all references to the Guidelines are to the 

2002 United States Sentencing Guidelines Manual.

2 The district court issued its dismissal order on November 20, 2017. 

Shipman filed a timely notice of appeal on December 5, 2017. Cross was 

decided on June 7, 2018, while Shipman’s appeal was pending. 
No. 17-3476 3

district courts to increase the offense level of a “career 

offender.” U.S.S.G. § 4B1.1. A defendant qualifies as a career 

offender if: (1) the defendant was at least 18 at the time of the

instant offense of conviction; (2) the offense of conviction is a 

“crime of violence or controlled substance offense”; and (3) 

the defendant has “at least two prior felony convictions of either a crime of violence or a controlled substance offense.”

§ 4B1.1.

When Shipman was sentenced in 2003, the Guidelines’ 

career-offender provisions defined a “crime of violence” (in 

relevant part) as: 

[A]ny offense under federal or state law, punishable by imprisonment for a term exceeding 

one year, that—

(2) is burglary of a dwelling, arson, or extortion, involves use of explosives, or otherwise involves conduct that presents a 

serious potential risk of physical injury to another.

U.S.S.G. § 4B1.2(a)(2) (emphasis added). Subsection (2) contains both the “enumerated-offenses clause” (non-italicized 

text) and the “residual clause” (italicized text).

The probation officer calculated a Guidelines sentencing 

range of 262 to 327 months’ imprisonment, based in part on 

Shipman’s designation as a career offender. Shipman’s age 

(35 years) and this drug charge supplied the first and second 

predicates for the career-offender designation. His three prior 

Arkansas convictions for “residential burglary” in 1986 and 

1987 satisfied the third predicate. Shipman did not object to 

the report’s career-offender designation or suggested
4 No. 17-3476

sentencing enhancement. The district court adopted the 

presentence report’s findings and calculations, classified 

Shipman as a career offender, and sentenced him to 262

months’ imprisonment. Neither the presentence report nor 

the district court explained whether Shipman’s career-offender designation rested on the enumerated-offenses clause 

or the residual clause.

A succession of Supreme Court decisions followed 

Shipman’s sentencing. First, the Supreme Court rendered the 

Guidelines “effectively advisory” in United States v. Booker, 

543 U.S. 220, 245 (2005). About a decade later the Supreme 

Court struck down the Armed Career Criminal Act’s (ACCA)

residual clause as unconstitutionally vague. Johnson v. United 

States, 135 S. Ct. 2551, 2257, 2563 (2015).3 Then, in Welch v. 

United States, 136 S. Ct. 1257, 1265 (2016), the Supreme Court 

held that Johnson applied retroactively on collateral review. 

Within one year of the Supreme Court’s decision in Johnson, 

Shipman petitioned for relief under § 2255. 

At this point, a word on § 2255 procedure is helpful. Section 2255(f)(1) establishes a “1-year period of limitation”

within which a federal prisoner may file a motion to vacate, 

set aside, or correct a sentence. In most cases, the one-year period begins to run when the judgment becomes final. 

Shipman invokes § 2255(f)(3), which sets a one-year filing 

deadline for postconviction relief starting from “the date on 

which the right asserted was initially recognized by the 

 3 See Johnson, 135 S. Ct. at 2564 (citing 18 U.S.C. § 924(e)(2)(B)(ii) (2012) 

(ACCA residual clause) (counting as a violent felony any crime that “otherwise involves conduct that presents a serious potential risk of physical 

injury to another”)). The ACCA’s residual clause used identical language 

as employed in U.S.S.G. § 4B1.2(a)(2).
No. 17-3476 5

Supreme Court, if that right has been newly recognized by the 

Supreme Court and made retroactively applicable to cases on 

collateral review.”

Shipman argued the Supreme Court’s decision in Johnson

recognized the right he asserted in his petition: to be resentenced because a vague residual clause fixed his term of imprisonment. Shipman’s petition, however, was not limited to 

a residual clause challenge—he claimed his drug sentence 

was improperly enhanced under the residual clause and enumerated-offenses clause of the Guidelines’ career-offender

provisions.

Shipman’s residual clause challenge was straightforward: 

a sentence under the Guidelines’ residual clause is unconstitutional because that clause is identical to the ACCA’s residual clause stricken in Johnson. Shipman’s second claim—that 

his burglary convictions do not qualify as predicate offenses 

under the Guidelines’ enumerated-offenses clause—was 

more intricate, relying on a chorus of additional Supreme 

Court decisions. 

Those arguments made, Shipman’s case was put on hold 

while multiple cases worked their way through the courts, 

among them Beckles v. United States, 137 S. Ct. 886 (2017). In 

Beckles, the Supreme Court held Johnson does not apply to sentences enhanced under post-Booker advisory Guidelines. Id. at 

895.

After Beckles, the district court lifted the stay and signaled

its intent to deny Shipman’s petition. The court observed that 

“following Beckles, there appears to be no legal basis” for 

Shipman’s void-for-vagueness challenge under Johnson, but it

offered Shipman an opportunity to respond. Shipman argued
6 No. 17-3476

Beckles applied only to prisoners sentenced under the advisory Guidelines (post-Booker), not the mandatory Guidelines

(pre-Booker).

Shipman failed to persuade the district court, which

denied Shipman’s petition as untimely. That court ruled a

defendant may rely on § 2255(f)(3) for timeliness purposes 

only “if the defendant’s entitlement to relief ... is so evident 

that it can no longer be considered an ‘open question.’” In the 

district court’s view, after Beckles it remained an open question whether Johnson’s reasoning extends to the pre-Booker

mandatory Guidelines.4 From that premise, the district court 

concluded Johnson did not commence a one-year limitation 

period, making Shipman’s petition untimely under 

§ 2255(f)(1). In concluding the petition was time-barred, the 

district court did not reach the merits of Shipman’s claims.

Although the district court dismissed Shipman’s petition

as untimely, it granted him a certificate of appealability on the 

issue.

II. DISCUSSION

We review the district court’s denial of Shipman’s § 2255 

petition de novo. D’Antoni v. United States, 916 F.3d 658, 662 

(7th Cir. 2019). Because Shipman filed his petition more than 

one year after his judgment became final, he must show the 

Supreme Court has “recognized” a new right to obtain

 4 See also Beckles, 137 S. Ct. at 903 n.4 (Sotomayor, J., concurring in 

judgment) (observing that Beckles’ holding leaves open the question 

whether pre-Booker Guidelines can be challenged for vagueness under due 

process principles).
No. 17-3476 7

postconviction relief. § 2255(f)(1), (3). Shipman again points to 

Johnson, and justifiably so. 

While Shipman’s appeal was pending, this court decided 

Cross, which held: “Under Johnson, the guidelines residual 

clause is unconstitutionally vague insofar as it determined 

mandatory sentencing ranges for pre-Booker defendants.” 892 

F.3d at 291. A petition challenging a career-offender enhancement under the mandatory Guidelines’ residual clause is 

timely under § 2255(f)(3) if it was filed within one year of 

Johnson. Id. at 294. Because Shipman met that deadline, his 

petition was not untimely.

We next assess whether we can resolve this case on the 

merits. A prisoner is entitled to a hearing on a § 2255 claim 

“[u]nless the motion and the files and records of the case conclusively show that the prisoner is entitled to no relief ... .” 

§ 2255(b). In other words, Shipman gets a hearing unless the 

record before us conclusively establishes he is not entitled to 

relief. First, we address Shipman’s residual clause challenge, 

and then turn to his challenge of a sentencing enhancement 

under the enumerated-offenses clause.

Shipman contends that, after Johnson and Cross, his Arkansas burglary convictions no longer fit under the Guidelines’

residual clause. The government objects, arguing the district 

court classified Shipman’s burglary convictions as crimes of 

violence under the enumerated-offenses clause, not the residual clause. Even if classified under the residual clause, the 

government asserts Shipman failed to raise a void-for-vagueness challenge when sentenced in 2003, and so procedurally 

defaulted on this claim. We start with the government’s procedural default objection.
8 No. 17-3476

In Cross, we held petitioners sentenced under the Guidelines’ residual clause (in its mandatory form) can demonstrate 

the requisite cause and prejudice to excuse procedural 

default. Cross, 892 F.3d at 294–96. Thus, if Shipman’s burglary 

convictions were classified under the residual clause, the government’s procedural default objection cannot stand under

Cross.

As for Shipman’s claim, Johnson and Cross are of no help 

to him unless he was sentenced under the residual clause. Section 2255(f)(3) does not require Shipman to prove at the outset 

that Johnson applies to his situation. Cross, 892 F.3d at 293–94

(holding an alternative interpretation of § 2255(f)(3) “improperly reads a merits analysis into the limitations period”). That 

said, neither Johnson nor Cross cleared a path to challenge 

every sentence under the mandatory career-offender 

Guidelines. See Sotelo v. United States, No. 16-4144, 2019 WL 

1950314, at *6 (7th Cir. May 2, 2019). Shipman must still “claim 

the benefit of a right that the Supreme Court has recently recognized.” Cross, 892 F.3d at 294. “Under Johnson, a person has 

a right not to have his sentence dictated by the unconstitutionally vague language of the mandatory residual clause.” 

Id. So Shipman must assert precisely that right for Johnson and 

Cross to apply.

In any event, we cannot make that determination because 

the district court never reached the issue. At Shipman’s 

sentencing, the district court made no mention whether the

burglary convictions rested on the enumerated-offenses 

clause or the residual clause. Shipman’s presentence report is 

similarly unavailing. Although the report concludes Shipman 

is a career offender under § 4B1.1, the report neither cites 

§ 4B1.2(a)(2) nor explains which career-offender provision 
No. 17-3476 9

was applied. Without knowing which provision the district 

court relied on to classify Shipman as a career offender, we 

cannot assess the merits of Shipman’s claim under Johnson

and Cross. 

Shipman’s second claim—that his Arkansas burglary 

convictions do not qualify under Guidelines’ enumerated-offenses clause—presents more detailed factual and legal questions. His argument takes aim at the Arkansas burglary 

statute in effect when he was convicted in 1986 and 1987, 

arguing it does not qualify for federal sentencing enhancements.

A state crime may qualify as a predicate conviction for 

federal sentencing purposes “only if the elements of the state 

crime mirror, or are narrower than, the elements of the generic crime.” United States v. Elder, 900 F.3d 491, 501 (7th Cir. 

2018) (citation omitted). When Shipman was sentenced, the 

enumerated-offenses clause listed “burglary of a dwelling” as 

one of several offenses constituting a crime of violence under 

the Guidelines’ career-offender provisions. § 4B1.2(a)(2). The 

Supreme Court defines “generic burglary” as “an unlawful or 

unprivileged entry into, or remaining in, a building or other 

structure, with intent to commit a crime.” Taylor v. United 

States, 495 U.S. 575, 598 (1990). The Arkansas burglary statute, 

however, included vehicles as “occupiable structures.” See 

Julian v. State, 298 Ark. 302, 303 (1989) (citing Ark. Code Ann. 

§ 5-39-101 (1987)). Because the Arkansas burglary statute

included vehicles, Shipman argues it was not generic and 

therefore does not qualify as a crime of violence.5

 5 Shipman cites a series of Supreme Court decisions to support this 

proposition: United States v. Stitt, 139 S.Ct. 399 (2018) (addressing the scope 
10 No. 17-3476

The government responds that all viable bases for 

Shipman to attack a career-offender designation under the 

enumerated-offenses clause were available at sentencing and 

within the one-year limitations period of § 2255(f)(1). The 

government also argues there has been no change in the law 

since then to justify Shipman’s reliance on § 2255(f)(3). But in 

this case, without an explanation of the career-offender 

designation, it is unclear how Shipman could object to that

categorization.

Although this appeal has narrowed the issues, the record 

does not “conclusively show” that Shipman “is entitled to no 

relief” on his claims, so remand is warranted for further findings on these questions. 28 U.S.C. § 2255(b). Given the state of 

the record, we express no opinion on the merits of Shipman’s 

claims, reserving that for the district court to evaluate and 

decide in the first instance.

III. CONCLUSION

Because our decision in Cross negates the underpinnings 

of the district court’s dismissal, we VACATE the district court’s 

order dismissing Shipman’s petition and REMAND the case to 

the district court for proceedings consistent with this opinion.

 

of generic burglary); Mathis v. United States, 136 S. Ct. 2243, 2251 (2016)

(“[A] state crime cannot qualify as an ACCA predicate if its elements are 

broader than those of a listed generic offense.”); see id. at 2250, 2257 (concluding that defendant’s prior burglary convictions cannot give rise to 

ACCA’s sentence enhancement because the elements of Iowa's burglary 

law, which includes entries into vehicles, are broader than those of generic 

burglary, which is limited to unlawful entry into a “building or other 

structure”); Taylor, 495 U.S. at 598 (defining “generic burglary”).