Jamar Plunkett v. Dan Sproul ( 2021 )

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 20-2461
JAMAR E. PLUNKETT,
Petitioner-Appellant,
v.
DAN SPROUL,
Respondent-Appellee.
____________________
Appeal from the United States District Court for the
Southern District of Illinois.
No. 19-cv-00655 — Nancy J. Rosenstengel, Chief Judge.
____________________
ARGUED SEPTEMBER 17, 2021 — DECIDED OCTOBER 20, 2021
____________________
Before SYKES, Chief Judge, and FLAUM, and KIRSCH, Circuit
Judges.
FLAUM, Circuit Judge. A grand jury indicted petitioner-ap-
pellant Jamar Plunkett on a charge of distributing crack co-
caine. Plunkett pleaded guilty after the government estab-
lished that his prior Illinois drug conviction subjected him to
an enhanced statutory maximum sentence. Plunkett now ap-
peals the district court’s decision to deny his § 2241 collateral
attack on his sentence. Plunkett, however, waived his
2 No. 20-2461
appellate rights, subject only to limited exceptions not pres-
ently applicable. Given this waiver, we now dismiss his ap-
peal.
I. Background
A. Underlying Criminal Case Proceedings
In January 2013, Plunkett sold crack cocaine to a confiden-
tial informant. A federal grand jury subsequently indicted
Plunkett on one count of distributing cocaine base, a Schedule
II controlled substance, in violation of 21 U.S.C. §§ 841(a)(1)
and 841(b)(1)(C). Convictions for offenses under
§ 841(b)(1)(C) carry a default statutory maximum sentence of
twenty years’ imprisonment. After Plunkett pleaded not
guilty, the government filed an information under 21 U.S.C.
§ 851 notifying the district court that Plunkett had a 2008 Illi-
nois felony conviction for unlawful delivery of cocaine in vi-
olation of 720 Ill. Comp. Stat. 570/401(d). The government as-
serted that this prior conviction qualified as a predicate “fel-
ony drug offense” under § 841(b)(1)(C) and thus subjected
Plunkett to an increased statutory maximum prison term of
thirty years for his federal drug offense.
Faced with a possible thirty-year prison term, Plunkett
reached an agreement with the government to plead guilty in
October 2013. In his plea agreement, Plunkett and the govern-
ment agreed that he qualified as a career offender and that his
advisory range under the U.S. Sentencing Guidelines was 188
to 235 months’ imprisonment. The government further
agreed to recommend a sentence at the low end of the sen-
tencing range. In return, Plunkett agreed to waive his rights
to appeal or collaterally attack his conviction or sentence, with
limited exceptions. Among these, Plunkett preserved his right
No. 20-2461 3
to seek collateral review based on any subsequent change in
the interpretation of the law declared retroactive by the Su-
preme Court or this Court that renders him actually innocent
of the charges against him.
The district court accepted Plunkett’s guilty plea. During
the change-of-plea hearing, the court informed Plunkett mul-
tiple times that he faced a statutory maximum sentence of
thirty years’ imprisonment and engaged him in a lengthy col-
loquy regarding his understanding of his waiver of his appeal
and collateral-attack rights.
The district court then held a sentencing hearing in Janu-
ary 2014. The court found that Plunkett qualified as a career
offender and faced a statutory maximum sentence of thirty
years’ imprisonment. The court further found that the Guide-
lines recommended an advisory sentencing range of 188 to
235 months’ imprisonment. Neither party objected to these
findings. Consistent with the terms of the plea agreement, the
government then recommended a low-end Guidelines sen-
tence of 188 months. The district court, however, rejected the
government’s recommendation and ultimately sentenced
Plunkett to 212 months in prison—two years above the Guide-
lines minimum—and six years of supervised release. The
court also imposed a $500 fine and a $100 assessment.
B. Collateral Challenges
1. Section 2255 Motion
Plunkett did not appeal his conviction or sentence, but in
January 2015 he filed a pro se motion in the district court to
vacate, set aside, or correct his sentence under 28 U.S.C.
§ 2255. In his motion, Plunkett argued that he received inef-
fective assistance of counsel because his lawyer did not
4 No. 20-2461
correctly calculate his Guidelines sentencing range and did
not appeal his sentence. He did not assert that the district
court incorrectly classified him as a career offender or errone-
ously found that his prior Illinois felony drug conviction sub-
jected him to an increased statutory maximum sentence un-
der § 841(b)(1)(C).
The district court denied Plunkett’s § 2255 motion, con-
cluding that Plunkett’s waiver of his appellate and collateral-
attack rights foreclosed his claims, which lacked merit in any
event. The court dismissed the motion with prejudice and did
not issue a certificate of appealability. Plunkett filed a motion
for reconsideration under Federal Rule of Civil Procedure
59(e), which the district court also denied.
2. Section 2241 Petition
In 2016, while Plunkett’s § 2255 motion remained pend-
ing, the U.S. Supreme Court issued its opinion in Mathis v.
United States, 136 S. Ct. 2243 (2016). That case reiterated that
(1) the modified categorical approach applies only to divisible
offenses, and (2) a state statute that lists alternative means, as
opposed to elements, of committing the state offense defines
a single, indivisible offense for the categorical analysis. See 136
S. Ct. at 2248, 2253, 2257. At the time, Plunkett did not seek to
supplement his pending § 2255 motion with any arguments
based on Mathis.
In June 2019, two years after the denial of his § 2255 mo-
tion, Plunkett challenged the use of his 2008 Illinois drug con-
viction to increase his statutory maximum sentence for the
first time. Plunkett filed a pro se petition for a writ of habeas
corpus under 28 U.S.C. § 2241 in the district court, asserting
that his challenge fell within § 2255(e)’s “saving clause”
No. 20-2461 5
exception that allows a prisoner to seek habeas relief under
§ 2241 when the remedy under § 2255 “is inadequate or inef-
fective to test the legality of his detention.” See 28 U.S.C.
§ 2255(e). His petition asserted that after Mathis and our sub-
sequent decision in United States v. Elder, 900 F.3d 491 (7th Cir.
2018), his 2008 Illinois conviction no longer qualified as a
predicate offense; he further contended that because of this
erroneous classification, his federal sentence was unlawfully
enhanced. Specifically, he argued that, under Mathis, the stat-
ute underlying his state conviction—720 Ill. Comp. Stat.
§ 570/401—was categorically overbroad because it criminal-
ized a broader range of conduct and substances than its fed-
eral counterpart. According to Plunkett, the erroneous appli-
cation of the increased statutory maximum sentence caused
him to suffer a miscarriage of justice because it resulted in an
increase in his Guidelines sentencing range based on his ca-
reer offender status. 1
The district court denied Plunkett’s § 2241 petition on pre-
liminary review. The court interpreted Plunkett’s argument
that his prior Illinois drug offense should not qualify as a fel-
ony drug offense as a challenge to his “designation and sen-
tence as a career offender.” The court then explained that
Plunkett’s career-offender sentence was imposed under the
advisory Sentencing Guidelines; therefore, our decision in
1 Specifically, Plunkett asserted that the increase in his statutory maxi-
mum sentence to thirty years based on his Illinois conviction resulted in
an offense level of 34 and a criminal history category of VI, which together
resulted in a Guidelines range of 262 to 327 months. Plunkett argued that
without the enhanced statutory penalty, his offense level would have been
31, resulting in a Guidelines range of 188 to 235 months. With a further
three-offense-level reduction for acceptance of responsibility, he asserted
that his Guidelines range would have been 140 to 175 months.
6 No. 20-2461
Hawkins v. United States, 706 F.3d 820 (7th Cir.), supplemented
on denial of reh’g, 724 F.3d 915 (7th Cir. 2013), which held that
errors in calculating advisory Guidelines ranges are not cog-
nizable on collateral review, precluded Plunkett’s challenge.
The district court further noted that even if Plunkett’s prior
Illinois convictions no longer pass muster after Mathis, he still
had not demonstrated the requisite fundamental defect in his
212-month sentence because it did not exceed the nonen-
hanced statutory maximum of 240 months for his offense. The
district court thus dismissed Plunkett’s § 2241 petition with
prejudice.
Plunkett again filed a motion for reconsideration. He as-
serted that the district court misinterpreted his petition as a
challenge to his career-offender designation, when in fact he
sought to challenge the use of his prior Illinois convictions as
predicate offenses for the career-offender enhancement. The
district court denied the motion. The court denied misunder-
standing the nature of Plunkett’s challenge and reiterated that
it would not grant relief because Plunkett’s final sentence fell
within the 240-month statutory maximum even absent the en-
hancement. The court also explained that the Supreme
Court’s decision in Brady v. United States, 397 U.S. 742 (1970),
foreclosed Plunkett’s argument that the allegedly erroneous
increase in the statutory maximum sentence distorted the plea
negotiations and influenced his decision to plead guilty; the
court noted that at the time he entered into the plea agree-
ment, Plunkett agreed with the government’s assessment that
his Illinois drug conviction exposed him to a sentence ranging
between 188 and 235 months. The district court concluded
that because his sentence fell squarely within that range, he
did not raise a viable habeas claim.
No. 20-2461 7
This appeal followed.
II. Discussion
Plunkett appeals the denial of his § 2241 petition, reassert-
ing many of the arguments he raised before the district court.
He contends that his collateral attack on his sentence falls
within § 2255(e)’s “saving clause” exception that allows a
prisoner to seek habeas relief under § 2241 when the remedy
under § 2255 “is inadequate or ineffective to test the legality
of his detention.” See 28 U.S.C. § 2255(e). The government, in
addition to responding to this argument, counters that Plun-
kett’s waiver of his collateral-attack rights in his plea agree-
ment precludes his § 2241 petition and requires dismissal of
this appeal. “Generally speaking, appeal waivers are enforce-
able and preclude appellate review.” United States v. Desotell,
929 F.3d 821, 826 (7th Cir. 2019) (quoting United States v.
Worthen, 842 F.3d 552, 554 (7th Cir. 2016)). Because we agree
with the government that Plunkett’s § 2241 challenge falls
within the scope of his voluntary and knowing collateral-at-
tack waiver, we do not reach the merits of his appeal.
A defendant may waive his right to challenge his sentence
on collateral review through a plea agreement, assuming such
waiver is knowing and voluntary. See Dowell v. United States,
694 F.3d 898, 901–02 (7th Cir. 2012); Fed. R. Crim. P.
11(b)(1)(N). We review de novo the enforceability of a collat-
eral attack waiver in a plea agreement. See Dowell, 694 F.3d at
901. “[A] valid and enforceable waiver … only precludes chal-
lenges that fall within its scope.” Garza v. Idaho, 139 S. Ct. 738,
744 (2019) (second alteration in original) (citation omitted).
“We generally enforce an appellate waiver if its terms are ex-
press and unambiguous and the record shows that it was
knowing and voluntary.” United States v. Bridgewater, 995 F.3d
8 No. 20-2461
591, 595 (7th Cir. 2021). In determining the scope of a waiver,
“‘[w]e interpret the terms of [a plea] agreement according to
the parties’ reasonable expectations’ and construe any ambi-
guities in the light most favorable to [the petitioner].’’ Dowell,
694 F.3d at 902 (first alteration in original) (quoting United
States v. Quintero, 618 F.3d 746, 751 (7th Cir. 2010)); see also
United States v. Galloway, 917 F.3d 604, 606–07 (7th Cir. 2019)
(“We interpret plea agreements—including appellate waivers
contained within them—according to ordinary principles of
contract law.”).
A. Scope of Plunkett’s Collateral-Attack Waiver
As described above, Plunkett’s plea agreement contained
a broad waiver of his right to seek collateral review of his con-
viction or sentence. Specifically, Plunkett acknowledged “that
Title 18, Title 28, and other provisions of the United States
Code afford every defendant limited rights to contest a con-
viction and/or sentence through appeal or collateral attack,”
but he agreed to “waive[] his right to contest any aspect of his
conviction and sentence that could be contested under Title
18 or Title 28, or under any other provision of federal law,”
other than to appeal the reasonableness of his sentence. Title
28 governs collateral attacks brought under § 2241 and § 2255.
Thus, by its terms, the waiver applies to Plunkett’s challenge
to his sentence.
Plunkett argues, however, that his petition falls outside
the ambit of the collateral-attack waiver because the plea
agreement preserved his right to challenge his sentence based
on “any subsequent change in the interpretation of the law by
the United States Supreme Court or the United States Court
of Appeals for the Seventh Circuit that is declared retroactive
by those Courts and that renders Defendant actually innocent
No. 20-2461 9
of the charges covered herein.” The parties do not dispute that
Plunkett challenges his sentence based on intervening statu-
tory decisions from the Supreme Court and this Court that
apply retroactively. 2
The determinative issue, therefore, is the meaning of
the phrase “actually innocent of the charges covered herein.”
The government essentially contends that this phrase refers
only to the underlying offense to which Plunkett pleaded
guilty in the agreement. 3 If this definition applies, Plunkett’s
challenge does not fall within the exception to his collateral-
attack waiver because he would remain guilty—that is, not ac-
tually innocent—of his federal drug offense, regardless of
whether he prevails on his challenge to his sentence. Plunkett,
on the other hand, argues that, when read in context, the
phrase also refers to the applicable sentence enhancement.
We agree with the government’s interpretation of the
waiver’s language. In interpreting plea agreements, we apply
2 Our Circuit has not always taken a uniform approach to answering ques-
tions about Mathis’s retroactivity. See Chazen v. Marske, 938 F.3d 851, 861
(7th Cir. 2019) (“We have likewise suggested (without deciding) that
Mathis is retroactive.”); see also Liscano v. Entzel, 839 F. App’x 15, 16 (7th
Cir. 2021) (“Our circuit’s decisions about the retroactivity of Mathis seem
to look in different directions.”). Because we need not reach a decision on
this issue to decide that Plunkett’s relied-upon exception is inapplicable
in this instance, we proceed, as the parties do, on the assumption that
Mathis applies retroactively on collateral review.
3 The government put forward the following definition of “charges” from
Law.com: “the specific statement of what crime the party is accused
(charged with) contained in the indictment or criminal complaint.” See
Charge, Law.com, https://dictionary.law.com/Default.aspx?typed=charge
&type=1 (last visited Oct. 20, 2021).
10 No. 20-2461
the ordinary principles of contract law and give unambiguous
terms their plain meaning. Galloway, 917 F.3d at 607.
“Charges”—and specifically “charges covered herein”—is
one such term. Black’s law dictionary defines a charge as “a
formal accusation of an offense as a preliminary step to pros-
ecution.” Charge, Black's Law Dictionary (11th ed. 2019). This
definition suggests that “charge” implies a connection to an
offense, which would exclude a sentencing enhancement and
which is in accord with common usage of the term.
Petitioner points to the government’s use of the phrase
“Charging Prior Offenses” to refer to the relevant prior drug
offense in its filing titled “Information as to Sentencing” to
suggest that the government itself refers to the sentencing en-
hancement as a “charge.” While this argument is not entirely
without merit, it is significantly undercut by the fact that this
document has no operative effect other than to provide the
sentencing court with information relevant to its sentencing
decision. See 21 U.S.C. § 851. It does not add a charge to the
indictment, nor does it indicate that the government will seek
to prosecute Plunkett for any additional offense. As its open-
ing sentence states, the document is merely “for use in en-
hancing any sentence rendered in this case ….”
The plea agreement itself extinguishes any lingering
doubt as to the meaning of “charges covered [t]herein.” The
only “charge[] covered [t]herein” is the charge for the distri-
bution of cocaine base. The plea agreement never refers to the
sentencing enhancement as a charge, and, in fact, language
from another provision of the agreement demonstrates that it
recognizes charges and sentencing enhancements as distinct.
That provision states that if the Defendant violates any provi-
sion of the plea agreement, “the Government is not bound by
No. 20-2461 11
the provisions herein and may request that the Court impose
on the Defendant any penalty allowable by law, including the
filing of additional charges or sentencing enhancement notices ….”
(emphasis added).
Given that the plea agreement refers to charges and sen-
tencing enhancements as distinct concepts and given that the
plain meaning of the term “charges” refers to charged of-
fenses, we hold that a successful challenge to his sentence
would not render Plunkett “actually innocent of the charges
covered” in the plea agreement. Therefore, this appeal falls
squarely into the category of appeals that Plunkett has waived
his right to bring.
B. Plunkett’s Waiver Was Knowing and Voluntary
Plunkett may nonetheless escape application of this
waiver if it was not knowing and voluntary. In determining
whether a waiver contained in a plea agreement was knowing
and voluntary, “we must examine the language of the plea
agreement itself and also look to the plea colloquy between
the defendant and the judge.” United States v. Chapa, 602 F.3d
865, 868 (7th Cir. 2010). A defendant’s waiver is knowing and
voluntary if he “understand[s] the choice confronting him
and … understand[s] that choice is his to make.” United States
v. Alcala, 678 F.3d 574, 579 (7th Cir. 2012) (alterations in origi-
nal) (quoting United States ex rel. Williams v. DeRobertis,
715 F.2d 1174, 1182–83 (7th Cir. 1983)); see also United States v.
Johnson, 934 F.3d 716, 719 (7th Cir. 2019) (explaining that we
consider circumstances surrounding the plea to “evaluat[e]
whether the district court ‘properly informed the defendant
that the waiver may bar the right to appeal’” (quoting United
States v. Shah, 665 F.3d 827, 837 (7th Cir. 2011))). “A written
appellate waiver signed by the defendant will typically be
12 No. 20-2461
voluntary and knowing, and thus enforceable through dis-
missal of a subsequent appeal.” Galloway, 917 F.3d at 606.
Plunkett asserts that he could not have knowingly and
voluntarily waived his right to collaterally attack his sentence
under Mathis because he did not know the correct statutory
maximum sentence when he pleaded guilty. We have long ex-
pressed the view, however, that plea-bargain appeal waivers
involve risk:
By binding oneself one assumes the risk of fu-
ture changes in circumstances in light of which
one’s bargain may prove to have been a bad
one. That is the risk inherent in all contracts;
they limit the parties’ ability to take advantage
of what may happen over the period in which
the contract is in effect.
United States v. Bownes, 405 F.3d 634, 636 (7th Cir. 2005). “That
the risk materialized for [Plunkett] does not trump the know-
ing and voluntary nature of his plea and waiver when he ac-
cepted the [g]overnment’s deal.” Alcala, 678 F.3d at 580.
Plunkett argues that our longstanding rule does not apply
to challenges, like his, based on intervening retroactive deci-
sions construing the statutory sentence applicable at the time
the defendant pleaded guilty. Here, Plunkett draws too fine a
distinction. “We have consistently rejected arguments that an
appeal waiver is invalid because the defendant did not antic-
ipate subsequent legal developments.” United States v.
McGraw, 571 F.3d 624, 631 (7th Cir. 2009). “[T]here is abun-
dant case law that appeal waivers … are effective even if the
law changes in favor of the defendant after sentencing,” even
if those changes are “unforeseen legal changes” that bring
No. 20-2461 13
about “a ‘sea change’ in the law.” Bownes, 405 F.3d at 636–37;
see also United States v. Vela, 740 F.3d 1150, 1151 (7th Cir. 2014)
(holding that a subsequent change in the law does not render
an appeal waiver involuntary). “The point of an appeal
waiver, after all, is to prospectively surrender one’s right to
appeal, no matter how obvious or compelling the basis for an
appeal may later turn out to be.” United States v. Smith,
759 F.3d 702, 707 (7th Cir. 2014); see also Oliver v. United States,
951 F.3d 841, 845 (7th Cir. 2020) (“[O]ne major purpose of an
express waiver is to account in advance for unpredicted fu-
ture developments in the law.”). As is the case with all con-
tracts, then, parties to plea agreements accept the risk that fu-
ture circumstances will change in ways that, had those cir-
cumstances existed at the time of the bargain, they may not
have agreed to so bind themselves. But bind himself Plunkett
did. And, per this Court’s precedent, a subsequent change in
the law regarding the statutory maximum sentence applicable
at the time he struck his deal does not render his waiver un-
knowing or involuntary.
The record here otherwise reveals that Plunkett know-
ingly and voluntarily waived his right to collaterally chal-
lenge his conviction and sentence. In addition to signing a
written waiver, which is presumed to be enforceable, see Gal-
loway, 917 F.3d at 606, Plunkett also attested in his plea collo-
quy—to which we lend “particular credence,” Alcala, 678 F.3d
at 578—to the fact that he made the waiver knowingly and
voluntarily. And there is simply nothing else in the record to
suggest otherwise.
14 No. 20-2461
III. Conclusion
Because Plunkett’s plea agreement contained a valid
waiver of his right to collaterally attack his sentence, this ap-
peal is DISMISSED.