Shane T. Watkins v. United States District Court for the Central District of Illinois

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 18-2967
S HANE T. WATKINS ,
Petitioner-Appellant,
v.
U NITED S TATES DISTRICT C OURT FOR THE
C ENTRAL DISTRICT OF I LLINOIS ,
Respondent-Appellee.*
____________________
Appeal from the United States District Court for the
Central District of Illinois.
No. 1:18-cv-01183-JBM — Joe Billy McDade, Judge.
____________________
A RGUED A PRIL 14, 2022 — DECIDED J UNE 16, 2022
____________________
* Before oral argument, the previous respondent—warden Steve Kal-
lis—filed a motion to substitute parties. He noted that petitioner had been
released from prison and had begun serving his term of supervised release
in the Central District of Illinois. Accordingly, we have substituted the
United States District Court for the Central District of Illinois as the re-
spondent. See Woodward v. United States District Court for the Eastern Dis-
trict of Michigan, No. 17-3591 (7th Cir. Mar. 31, 2022) (substituting district
court as respondent where petitioner was on supervised release).

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2 No. 18-2967
Before S YKES , Chief Judge, and HAMILTON and S CUDDER ,
Circuit Judges.
HAMILTON , Circuit Judge. This appeal presents several
challenging issues related to the “categorical approach” to
federal recidivist sentencing enhancements and the availabil-
ity of collateral relief from criminal convictions and sentences
under 28 U.S.C. § 2241. As it turns out, however, we need not
resolve these difficult questions because the case is moot.
Back in 2004, petitioner Shane T. Watkins was convicted
under federal law of possessing crack cocaine with intent to
distribute. He received a mandatory life sentence based on
three prior convictions for “felony drug offenses.” After mul-
tiple unsuccessful collateral attacks, Watkins filed this § 2241
petition. Invoking the Supreme Court’s decision in Mathis v.
United States, 579 U.S. 500 (2016), he argues that two of his
prior convictions do not qualify as predicate felony drug of-
fenses under 21 U.S.C. § 841(b)(1)(A), so his enhanced sen-
tence was unlawful. Without contesting the merits of that ar-
gument, the government asserts, among other things, that
Watkins has abused the writ of habeas corpus and that he
does not meet the requirements to seek the habeas remedy
provided in § 2241.
The problem for this appeal stems from good news for
Watkins. Following enactment of the First Step Act of 2018, he
applied for relief under that statute. He was resentenced to
time served and released from prison. He is currently serving
a reduced term of supervised release. Watkins says that a fa-
vorable decision on the merits here could lead to a further re-
duction in his supervised release term, but any help we might
provide in that effort is too speculative to keep the case alive.
We therefore vacate the judgment and remand with

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No. 18-2967 3
instructions to dismiss the petition as moot. See United States
v. Munsingwear, Inc., 340 U.S. 36, 39 (1950).
I. Factual and Procedural Background
A. Initial Sentence and Appeal
In 2004, a jury convicted Watkins under federal law for
possessing more than fifty grams of crack cocaine with intent
to distribute. Before trial, the government had filed a notice of
intent under 21 U.S.C. § 851 to seek an enhanced sentence
based in part on three prior drug convictions. One of those
convictions was for possession of cocaine in violation of fed-
eral law. The other two were for possession of cocaine and
delivery of cocaine in violation of the Illinois Controlled Sub-
stances Act, 720 ILCS 570/401(d) (1999). When Watkins was
convicted in 2004, § 841(b) called for a mandatory life sen-
tence for a defendant with two or more prior convictions for
felony drug offenses. See 21 U.S.C. § 841(b)(1)(A) (2004); see
also § 802(44) (“The term ‘felony drug offense’ means an of-
fense that is punishable by imprisonment for more than one
year under any law of the United States or of a State … that
prohibits or restricts conduct relating to narcotic drugs, mari-
huana, anabolic steroids, or depressant or stimulant sub-
stances.”).
At sentencing, Watkins did not dispute that he had two
such prior convictions. Judge McDade, who had presided at
Watkins’ trial, said that a life sentence for the offense was
“horrific” and described the case as “a perfect example of one
of the evils of mandatory minimums.” As required by statute,
however, the judge imposed the mandatory sentence of life in
prison, as well as the mandatory minimum ten-year term of
supervised release. Watkins appealed. He challenged the

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4 No. 18-2967
partial denial of a pre-trial motion to suppress but did not
challenge his sentence. This court affirmed. United States v.
Watkins, 175 F. App’x 53, 58 (7th Cir. 2006).
B. Collateral Relief Proceedings
In 2007, Watkins filed a motion for relief under 28 U.S.C.
§ 2255. In an amended motion, he argued that he had received
ineffective assistance of counsel and that one of his prior con-
victions should have been classified as a misdemeanor rather
than as a felony drug offense. Judge McDade denied his mo-
tion in 2009.
Seven years later, the Supreme Court decided Mathis v.
United States, 579 U.S. 500 (2016). As we have said, Mathis pro-
vided guidance on the “categorical approach for classifying
prior convictions for purposes of recidivist sentencing en-
hancements.” Guenther v. Marske, 997 F.3d 735, 739 (7th Cir.
2021). The categorical approach matters to defendants who
have received enhanced sentences based on prior convictions
because it is used to “determine whether [a] state conviction
can serve as a predicate offense by comparing the elements of
the state statute of conviction to the elements of the federal
recidivism statute.” United States v. Elder, 900 F.3d 491, 501
(7th Cir. 2018).
A few months after Mathis was decided, Watkins filed his
first petition for a writ of habeas corpus under 28 U.S.C.
§ 2241. Relying on Mathis, he argued that his prior drug con-
victions did not qualify as controlled substance offenses un-
der the Sentencing Guidelines, so the enhanced sentence he
received was unlawful. Judge Shadid denied Watkins’ peti-
tion. The judge first noted that Watkins’ designation as a ca-
reer offender under the Guidelines was “irrelevant” because

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No. 18-2967 5
“his sentence was based on the statutory minimum sentence
rather than the career offender guideline.” In any event, the
judge concluded, Watkins’ three prior drug convictions all
qualified as felony drug offenses, even after Mathis.
Watkins then filed this second § 2241 petition. This time,
he asserted that his sentence was unlawful because the statu-
tory enhancement was erroneous. Again citing Mathis, Wat-
kins argued that his Illinois convictions did not qualify as fel-
ony drug offenses under the categorical approach because the
Illinois drug statute under which he was convicted swept
more broadly than federal law. He also asserted that a § 2241
petition was the proper vehicle for relief. A convicted peti-
tioner seeking relief under § 2241 must show that
(1) the claim relies on a statutory interpretation
case, not a constitutional case, and thus could
not have been invoked by a successive § 2255
motion; (2) the petitioner could not have in-
voked the decision in his first § 2255 motion and
the decision applies retroactively; and (3) the er-
ror is grave enough to be deemed a miscarriage
of justice.
Franklin v. Keyes, 30 F.4th 634, 643 (7th Cir. 2022), quoting Cha-
zen v. Marske, 938 F.3d 851, 856 (7th Cir. 2019). Watkins argued
that these conditions were satisfied because Mathis—a statu-
tory interpretation case—had not been decided at the time he
filed his § 2255 motion and because he had received an im-
proper life sentence.
Judge McDade dismissed this second § 2241 petition. The
judge invoked the abuse-of-the-writ doctrine, concluding that
“any claim based on Mathis was available to Watkins when he

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6 No. 18-2967
filed his first § 2241 petition in late 2016.” And regardless,
Judge McDade said, Watkins could not raise an independent
Mathis claim in a § 2241 petition because Mathis did not create
a new rule.
Watkins appealed. While his appeal was pending, Con-
gress passed the First Step Act of 2018, Pub. L. No. 115-391,
132 Stat. 5194. As relevant here, section 404 of the Act allows
defendants convicted of certain crack cocaine offenses to
move for reduced sentences. See United States v. Shaw, 957
F.3d 734, 739–40 (7th Cir. 2020). Watkins filed such a motion
in January 2019, almost fifteen years into his life sentence.
Judge McDade resentenced him to time served and imposed
a reduced eight-year term of supervised release.
In this appeal from the denial of his second § 2241 petition,
Watkins argues that he was erroneously subjected to a man-
datory life sentence and that the conditions for proceeding
under § 2241 are satisfied. The government offers several rea-
sons to reject the petition, arguing that the case is moot, that
Watkins abused the writ, and that Watkins cannot pursue re-
lief under § 2241. Because we agree that Watkins’ case is moot,
we do not decide the other issues.
II. Mootness
Article III of the Constitution limits the judicial power to
“resolving live ‘Cases’ and ‘Controversies,’ rather than issu-
ing advisory opinions.” E.F.L. v. Prim, 986 F.3d 959, 962 (7th
Cir. 2021), quoting U.S. Const. art. III, § 2. To invoke federal
jurisdiction, therefore, a plaintiff must have “a ‘personal
stake’ in the outcome of the action.” United States v. Sanchez-
Gomez, 138 S. Ct. 1532, 1537 (2018), quoting Genesis Healthcare
Corp. v. Symczyk, 569 U.S. 66, 71 (2013). That requirement

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No. 18-2967 7
extends to all stages of the litigation, “not merely … the time
the complaint is filed.” Id., quoting Preiser v. Newkirk, 422 U.S.
395, 401 (1975). If intervening circumstances deprive the
plaintiff of a personal stake in the outcome, “the action can no
longer proceed and must be dismissed as moot.” Genesis
Healthcare, 569 U.S. at 72. Courts have a “‘constitutional obli-
gation to resolve the question of mootness’ and address it sua
sponte if needed.” E.F.L., 986 F.3d at 962–63, quoting United
States v. Fischer, 833 F.2d 647, 648 n.2 (7th Cir. 1987).
A case is moot “only when it is impossible for a court to
grant any effectual relief whatever to the prevailing party.”
Chafin v. Chafin, 568 U.S. 165, 172 (2013), quoting Knox v. Ser-
vice Employees International Union, Local 1000, 567 U.S. 298, 307
(2012). Where the parties “have a concrete interest, however
small, in the outcome of the litigation, the case is not moot.”
Knox, 567 U.S. at 307–08, quoting Ellis v. Brotherhood of Railway,
Airline & Steamship Clerks, 466 U.S. 435, 442 (1984). But a po-
tential injury that is “too speculative cannot serve as the
source of a party’s interest in a case.” United States v. Shorter,
27 F.4th 572, 575 (7th Cir. 2022).
Shorter illustrates the limits of speculation when evaluat-
ing mootness. In that case, the defendant appealed the district
court’s denial of his motion for compassionate release. After
the appeal was filed, the defendant was released from prison
and placed on home confinement for the remainder of his sen-
tence, with a three-year term of supervised release to follow.
We held that the case was moot because the defendant’s re-
quested relief had been accomplished by his release to home
confinement. That conclusion was not affected by the fact that
the defendant “hypothetically could return to prison through
a violation of the conditions of either his home confinement

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8 No. 18-2967
or his supervised release.” 27 F.4th at 576 (internal citation
omitted). “Any chain of events leading to [the defendant’s]
potential return to the prison,” we said, was “too speculative
to provide him with a constitutionally cognizable stake in this
case.” Id.1
Nor was speculation sufficient to avoid mootness in
Eichwedel v. Curry, 700 F.3d 275 (7th Cir. 2012). There, a habeas
petitioner challenged the revocation of his good-conduct
credits by the Illinois Department of Corrections. While the
appeal was pending, his credits were restored and he began
his term of supervised release. The petitioner said that the
case was not moot because he could have applied for up to
ninety days of good-time credits if his own credits had not
been revoked. As a result, he could have been released ninety
days earlier and completed his supervised release sooner. We
rejected those arguments, concluding that the petitioner could
point to only “the possibility that he might have served a
shorter period of incarceration before beginning his period of
supervised release.” Id. at 279. From there, “prison authorities
might have seen fit to grant him a reduction in the days he had
to serve.” Id. Those possibilities were “not sufficient to estab-
lish a continuing controversy.” Id.
To picture any effective relief in this case, we would need
to imagine a similarly attenuated chain of events built on es-
calating levels of speculation. First, as a preliminary matter, if
we vacated Watkins’ sentence, the district court would then
1 Both parties in Shorter agreed that the case should be dismissed as
moot, but defense counsel did not file a form signed by the defendant in-
dicating that he had consented to dismissal. We therefore addressed the
substance of the mootness issue. See Shorter, 27 F.4th at 575 & n.2.

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No. 18-2967 9
have to resentence Watkins to twenty years’ imprisonment—
since that is the mandatory minimum he would have been
subject to based on his predicate federal conviction alone. See
21 U.S.C. § 841(b)(1)(A) (2004). (The reduced mandatory min-
imum sentences under section 401 of the First Step Act did not
automatically apply to already-sentenced defendants.) Wat-
kins would then need to re-apply for relief under the First
Step Act. The district court would then have to hold another
First Step Act hearing, weigh the relevant factors, and con-
clude that Watkins was entitled to a reduced sentence even
lower than the fifteen years he already served. Finally, one of
two things would need to happen. Either the district court
would have to exercise its considerable discretion under 18
U.S.C. § 3583(e) to reduce Watkins’ term of supervised release
to less than eight years or Watkins would have to violate his
supervised release conditions and use the excess prison time
he served as banked time against any new term of imprison-
ment.
At each step, Watkins can only speculate that he might
benefit from a decision on the merits. Consider the new First
Step Act hearing Watkins would receive after being resen-
tenced to the twenty-year mandatory minimum, having al-
ready completed a reduced sentence of the fifteen years he
had already served. In essence, Watkins is arguing that the
district court might be inclined to impose a new reduced sen-
tence even lower than fifteen years if it had a determination
from this court that the original sentence was unlawful. But
that is pure guesswork. At the original First Step Act hearing,
the district court already exercised its discretion in consider-
ing a potential sentence reduction. See United States v.
McSwain, 25 F.4th 533, 537 (7th Cir. 2022) (noting that First
Step Act “establishes that the decision whether to reduce a

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10 No. 18-2967
defendant’s sentence, and by how much, is a decision com-
mitted to the discretion of the district court”); United States v.
Fowowe, 1 F.4th 522, 527 (7th Cir. 2021) (emphasizing district
court’s “discretion in determining whether and how much to
reduce a defendant’s sentence” under First Step Act). The
court then granted Watkins exactly what his attorney had re-
quested: a reduced sentence of time served. A remote possi-
bility that the court might go even lower—when it would not
actually shorten Watkins’ prison time—if we were to reach the
merits is not enough to save the case from mootness. Cf.
United States v. Juvenile Male, 564 U.S. 932, 937 (2011) (holding
that a “possible, indirect benefit in a future lawsuit cannot
save this case from mootness”).
Even if Watkins could overcome that hurdle, his argument
requires further speculation at the next step. He says that a
new sentence lower than fifteen years might help him win a
reduced term of supervised release. Under 18 U.S.C.
§ 3583(e), a defendant may move for early termination of su-
pervised release. See, e.g., United States v. Hassebrock, 21 F.4th
494, 496 (7th Cir. 2021). The statute provides that a district
court may “terminate a term of supervised release and dis-
charge the defendant released at any time after the expiration
of one year of supervised release … if it is satisfied that such
action is warranted by the conduct of the defendant released
and the interest of justice.” § 3583(e)(1). The court may do so,
however, only after “considering the factors set forth in sec-
tion 3553(a)(1), (a)(2)(B), (a)(2)(C), (a)(2)(D), (a)(4), (a)(5),
(a)(6), and (a)(7).” § 3583(e). Given the wide discretion in con-
sideration of the § 3553(a) factors, see, e.g., United States v. Gib-
son, 996 F.3d 451, 469 (7th Cir. 2021), the mere possibility that
our decision might influence the court’s determination on re-
mand is not enough to keep the case alive. See Phifer v. Clark,

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No. 18-2967 11
115 F.3d 496, 500 (7th Cir. 1997) (“[A]n event’s potential influ-
ence on future discretionary decisions is insufficient to save a
claim from mootness.”), citing Lane v. Williams, 455 U.S. 624,
632–33 (1982).
Nor do we see why Watkins needs a decision on the merits
from our court to prevail in a possible future § 3583(e) pro-
ceeding. There is no dispute that Watkins’ sentence was im-
properly enhanced based on the Illinois convictions. In fact,
the government has said in its brief that it would concede as
much in any proceeding for early termination of supervised
release under § 3583(e). Watkins responds that such a conces-
sion is not sufficient and that the district court has shown an
“unwillingness” to revisit the conclusion that his prior con-
victions are felony drug offenses. The district court decision
he refers to, however, was issued in August 2018—before all
the cases Watkins relies on to argue that the relevant provision
of the Illinois statute is categorically overbroad. See United
States v. Oliver, 987 F.3d 794 (8th Cir. 2021); United States v.
Ruth, 966 F.3d 642 (7th Cir. 2020); United States v. De La Torre,
940 F.3d 938 (7th Cir. 2019); Najera-Rodriguez v. Barr, 926 F.3d
343 (7th Cir. 2019).
This intervening case law, combined with the govern-
ment’s concession, should be more than enough to make clear
in a § 3583(e) proceeding that Watkins was not properly sub-
ject to a mandatory life sentence. Whether that warrants a fur-
ther reduction in Watkins’ term of supervised release is a
question for the district court to answer, but it is not a ques-
tion that would be affected one way or the other by our decid-
ing the merits here. Any ruling we issued would therefore
amount to an advisory opinion in violation of “the oldest and
most consistent thread in the federal law of justiciability.”

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12 No. 18-2967
Flast v. Cohen, 392 U.S. 83, 96 (1968) (citation omitted); see also
Muskrat v. United States, 219 U.S. 346, 354 (1911) (discussing
Supreme Court’s refusal to issue advisory opinion in 1793).
Aside from relief under § 3583(e), Watkins argues, a new
reduced sentence below fifteen years would allow him to re-
ceive “banked” time credit toward any prison sentence for
any future violation of his supervised release conditions. He
cites Bureau of Prisons regulations providing that “’[a]ny
prior custody time spent in official detention after the date of
offense that was not awarded to the original sentence or else-
where shall be awarded to the revocation term’ when a de-
fendant is sentenced to a term of incarceration for violating
his supervised release.” United States v. Jackson, 952 F.3d 492,
498 (4th Cir. 2020)(alteration in original), quoting BOP Pro-
gram Statement § 5880.28, Sentence Computation Manual-
CCCA of 1984 (1999) at 1-69.
Again, however, this argument is contingent on several
different events occurring. Watkins admits that there are no
revocation proceedings under way, so this potential benefit
would become available only if he (1) received a sentence
lower than fifteen years on remand; (2) violated his super-
vised release conditions; and (3) was sentenced to another
term of incarceration, at which point his banked time could
be awarded against the new term. That possibility is too far
removed from the current proceedings to render this a live
case or controversy under Article III. See Shorter, 27 F.4th at
576 (finding compassionate release appeal moot even though
defendant hypothetically could have returned to prison upon
future violation of supervised release conditions); cf. Phifer,
115 F.3d at 500 (“A habeas petition can play no role in

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No. 18-2967 13
sheltering someone from his or her own possible future mis-
conduct.”).2
Resisting the government’s arguments that any potential
relief is too speculative, Watkins relies heavily on Pope v. Per-
due, 889 F.3d 410 (7th Cir. 2018). But that case does not compel
a different conclusion. There, the petitioner argued that the
Bureau of Prisons had erroneously extended the length of his
sentence. While his appeal proceeded, he was released from
prison and began serving his term of supervised release. His
release did not moot the case, however, because “a finding
that Pope spent too much time in prison … would carry ‘great
weight’ in a § 3583(e) motion” to reduce Pope’s term of super-
vised release. Id. at 414, quoting United States v. Johnson, 529
U.S. 53, 60 (2000). Even though § 3583(e) had required the
court to impose a minimum term of supervised release, we
recognized that the court could terminate that term early if it
was “satisfied that such action is warranted by the conduct of
the defendant released and the interest of justice.” Id., quoting
§ 3583(e)(1).
This case differs from Pope because no finding by this court
could establish that Watkins spent more time in prison than
the law allowed. Recall that the government sought an en-
hanced sentence for Watkins based on three prior drug con-
victions: one federal conviction and two Illinois convictions.
As noted above, even if the sentencing court had relied on
2 Watkins noted in his reply brief that he was then being held in
county jail for allegedly possessing a stolen vehicle in violation of state
law. At oral argument, his counsel reported that all charges had been
dropped but that the government had filed a petition to revoke his super-
vised release. A few weeks later, however, the government moved to dis-
miss the petition to revoke, and the district court granted that motion.

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14 No. 18-2967
only the federal conviction—which Watkins’ § 2241 petition
does not challenge—Watkins still would have faced a mini-
mum of twenty years in prison. Under the First Step Act, how-
ever, he was released after serving fifteen years. This is not a
case where we can find that the petitioner “spent too long in
prison.” Pope, 889 F.3d at 415.3
The judgment of the district court is VACATED, and the
case is REMANDED with instructions to dismiss the petition
as moot.
3 For similar reasons, United States v. Trotter, 270 F.3d 1150 (7th Cir.
2001), also does not help Watkins. In that case, a favorable decision on the
merits would have reduced the defendant’s guideline range from 6–12
months to 4–10 months. Id. at 1152. But here, as Watkins concedes, his stat-
utory range would remain the same even if we resolved the merits in his
favor.

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