Tracy D. Shipman v. United States of America

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 17-3476
TRACY D. S HIPMAN ,
Petitioner-Appellant,
v.
U NITED S TATES OF A MERICA,
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.
____________________
A RGUED F EBRUARY 22, 2019 — DECIDED J UNE 5, 2019
____________________
Before R IPPLE, M ANION , and BRENNAN , Circuit Judges.
BRENNAN , Circuit Judge. Tracy Shipman appeals the dis-
trict 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 un-
der the then-mandatory Sentencing Guidelines. Because Ship-
man had three prior “crime of violence” felony convictions,
the district court sentenced him as a “career offender.”

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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 re-
solved, 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 re-
mand this case for further proceedings on the merits of Ship-
man’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 manufac-
ture 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.

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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 ei-
ther 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, pun-
ishable by imprisonment for a term exceeding
one year, that—
(2) is burglary of a dwelling, arson, or ex-
tortion, involves use of explosives, or oth-
erwise involves conduct that presents a
serious potential risk of physical injury to an-
other.
U.S.S.G. § 4B1.2(a)(2) (emphasis added). Subsection (2) con-
tains 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

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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-of-
fender 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. Sec-
tion 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 pe-
riod 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 “oth-
erwise 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).

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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 resen-
tenced because a vague residual clause fixed his term of im-
prisonment. 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 enu-
merated-offenses clause of the Guidelines’ career-offender
provisions.
Shipman’s residual clause challenge was straightforward:
a sentence under the Guidelines’ residual clause is unconsti-
tutional because that clause is identical to the ACCA’s resid-
ual 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 sen-
tences 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

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6 No. 17-3476
Beckles applied only to prisoners sentenced under the advi-
sory 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 ques-
tion 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).

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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 enhance-
ment 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 con-
clusively 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 Arkan-
sas 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 resid-
ual clause. Even if classified under the residual clause, the
government asserts Shipman failed to raise a void-for-vague-
ness challenge when sentenced in 2003, and so procedurally
defaulted on this claim. We start with the government’s pro-
cedural default objection.

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8 No. 17-3476
In Cross, we held petitioners sentenced under the Guide-
lines’ 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 gov-
ernment’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. Sec-
tion 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) “improp-
erly 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 rec-
ognized.” Cross, 892 F.3d at 294. “Under Johnson, a person has
a right not to have his sentence dictated by the unconstitu-
tionally 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

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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-of-
fenses clause—presents more detailed factual and legal ques-
tions. 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 enhance-
ments.
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 ge-
neric 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

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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 find-
ings 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 R EMAND 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 (con-
cluding 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”).

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