United States of America v. Roy Crockett, Jr.

United States Court of Appeals
For the Seventh Circuit
Chicago, Illinois 60604
Argued January 25, 2023
Decided May 17, 2023
Before
DIANE S. SYKES, Chief Judge
DIANE P. WOOD, Circuit Judge
DORIS L. PRYOR, Circuit Judge
No. 20-3025
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
ROY CROCKETT, JR.,
Defendant-Appellant.
Appeal from the United States District
Court for the Eastern District of Wisconsin.
No. 19-CR-86
Lynn Adelman,
Judge.
O R D E R
Roy Crockett, Jr., pleaded guilty to two counts of possessing a firearm and
ammunition as a felon, and he was sentenced under the Armed Career Criminal Act
(ACCA). The ACCA enhanced his sentence if, as he conceded in the district court, he
committed three prior qualifying felonies on “occasions different from one another[.]”
18 U.S.C. § 924(e)(1). Crockett’s plea agreement included a waiver of his right to appeal.
Here, Crockett seeks to invalidate his plea on the ground that Wooden v. United States,
NONPRECEDENTIAL DISPOSITION
To be cited only in accordance with FED. R. A PP. P. 32.1

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142 S.Ct. 1063 (2022), altered this court’s interpretation of different “occasions,” so that
his plea was not voluntary or knowing. Because Crockett’s appeal waiver assumed the
risk of this legal development, it blocks his appeal. Therefore, we dismiss the appeal.
I
From 1998 until 2016, Crockett was incarcerated for three felony convictions,
including: carjacking in Norfolk, Virginia, and robbery and carjacking in Hampton,
Virginia. In 2016, Crockett was released from Virginia state prison, with portions of his
remaining sentences suspended.
In 2019, Crockett was arrested by federal authorities with guns, hundreds of
rounds of ammunition and body armor. Following the arrest, Crockett was charged
with two counts of possessing a firearm as a felon, 18 U.S.C. § 922(g)(1), and one count
of possessing body armor as a violent felon, 18 U.S.C. § 931. Based on the three prior
convictions, the Indictment also charged Crockett pursuant to 18 U.S.C. § 924(e)(1), the
ACCA sentencing provision. Crockett pleaded guilty, pursuant to a plea agreement,
which charged him by Information with two counts of being a felon in possession of a
firearm. The Information alleged that he was subject to the ACCA sentencing
enhancement and listed his prior convictions.
In his plea agreement, Crockett agreed that he was subject to a sentencing
enhancement under the ACCA and agreed not to move “to withdraw the guilty plea
solely as a result of a determination that he is an Armed Career Criminal.” The ACCA
requires that anyone who violates 18 U.S.C. § 922(g) and has three prior convictions for
violent felonies that were “committed on occasions different from one another” be
imprisoned for a minimum of 15 years. See 18 U.S.C. § 924(e)(1). Crockett stipulated that
three of his prior convictions—namely, his one armed robbery and two carjacking
convictions—“resulted from offenses that occurred on three different occasions.”
Regarding these convictions, the plea agreement1 listed the charges, the date of
conviction, the case number, and the court that convicted him. Crockett moves to
supplement the record with the related charging documents and police reports to show
that the two carjackings occurred on the same night and were, he says, part of a
common scheme. We address this motion later.
1 The plea agreement erroneously says that Crockett’s prior offenses were two armed robbery charges
and one carjacking charge. This is incorrect, however, neither party contends that this clerical error is
material.

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The plea agreement also contains an appellate waiver. It states that Crockett
“knowingly and voluntarily waives his right to appeal his conviction or sentence,”
including to appeal based on a claim that the conduct he admitted to did “not fall
within the scope of the statutes or Sentencing Guidelines.” The waiver excludes, among
other things, appeals based on “punishment in excess of the statutory maximum” and
“a claim that the plea agreement was entered involuntarily.”
In exchange for the plea and waiver, the government made several concessions.
It recommended that the mandatory minimum sentence of 180 months imprisonment
under the ACCA run concurrently on both counts. It also agreed to recommend, in
total, a three-level decrease under the Sentencing Guidelines for acceptance of
responsibility, and to dismiss the body armor count.
The district judge conducted a plea colloquy, pursuant to Rule 11 of the Federal
Rules of Criminal Procedure, and accepted the plea agreement. The judge confirmed
that Crockett had discussed the plea deal with his attorney, was pleading guilty
voluntarily, and understood the rights he was waiving, including his “right to appeal or
challenge” his conviction or sentence. Also, the judge asked whether the facts in the
plea agreement were “substantially correct.” Crockett stated that they were. Finally, the
judge confirmed that Crockett understood that he was facing “a minimum of 15 years to
life” on each count.
Next, a probation officer prepared a presentence investigation report. The PSR,
noting that Crockett was subject to the ACCA, calculated Crockett’s offense level as 30
and his criminal-history category as IV. And it stated that under the ACCA, the
mandatory-minimum imprisonment term was 180 months. Crockett did not object to
the PSR’s sentencing calculation.
At the sentencing hearing, the district judge adopted the PSR and heard from
counsel. Crockett’s lawyer argued, in mitigation, that Crockett was “concerned for his
faith community” and, admittedly wrongly, armed himself to protect his family and his
mosque. In addition, the Government jointly recommended with Crockett that any
federal sentence run concurrently with his two outstanding Virginia cases. The judge
acknowledged “positive things” Crockett had done, including that he was “actively
involved with his mosque,” but stated that “[u]nfortunately, this [was] not like a
sentence where the judge has any real power,” except to apply the mandatory
minimum. The judge imposed the mandatory minimum of 180 months on both counts

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to run concurrent with each other and to any suspended state sentence, as the parties
had jointly recommended.
II
Our analysis begins with the appeal waiver. Appeal waivers generally “must be
enforced” if the “terms are express and unambiguous, and the record shows that the
defendant knowingly and voluntarily entered into the [plea] agreement.” United States
v. Nulf, 978 F.3d 504, 506 (7th Cir. 2020) (quoting United States v. Haslam, 833 F.3d 840,
844 (7th Cir. 2016) (alteration in original)). Crockett urges this court to set aside the
appeal waiver for two reasons. First, he argues that Wooden revealed that this court’s
previous interpretation of the ACCA was incorrect and, therefore, his underlying plea
was not knowing and voluntary. See FED. R. C RIM. P. 11(b)(1)(G). Second, he argues that
the sentence exceeds the statutory maximum because the ACCA charge lacked an
adequate factual basis. Neither argument is availing.
A. Knowing and Voluntary Plea
Crockett’s core argument is that his plea is invalid because Wooden altered this
court’s interpretation of the word “occasions” in the ACCA. Wooden held that to
determine whether predicate offenses occurred on different “occasions” under the
ACCA, several factors are relevant including “[t]iming,” “intervening events,”
“[p]roximity,” and “the character and relationship of the offenses[.]” 142 S.Ct. at 1071.
Before Wooden, this court had held that offenses occurred on different “occasions” as
long as the defendant had an “opportunity to stop and proceed no further,” and the
offenses were not committed simultaneously. United States v. Elliott, 703 F.3d 378, 383
(7th Cir. 2012). Wooden altered that understanding. 142 S.Ct. at 1068-69 (abrogating
United States v. Morris, 821 F.3d 877 (7th Cir. 2016)).
Because Wooden changed the meaning of different “occasions,” Crockett argues,
he was misinformed about a critical element of his offense, rendering his plea invalid.
To prove that he was misinformed, he relies heavily on Bousley v. United States, 523 U.S.
614 (1998). There, a defendant argued that the Supreme Court’s reinterpretation of the
offense to which he had pleaded guilty meant that the district court had misinformed
him about the elements. Id. at 617–18. Although it did not decide the case on that
ground, id. at 624, the Court stated that if the defendant could prove that neither he, his

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attorney, “nor the court correctly understood the essential elements of the crime with
which he was charged,” his guilty plea was “constitutionally invalid.” Id. at 618-19.
The problem for Crockett in relying on Bousley is that the defendant in that case
was not bound by an appeal waiver, and if Crockett’s appeal waiver is valid, the waiver
prevents this court from considering his argument about Bousley. Crockett, therefore,
must explain why his appeal waiver is invalid. To do so, he repeats that Wooden
revealed that no one at his plea hearing—neither Crockett, his attorney, nor the judge—
knowingly or intelligently understood the “occasions” element of the ACCA; therefore,
like in Bousley, his plea is invalid. And because “an appeal waiver stands or falls with
the underlying agreement and plea,” Nulf, 978 F.3d at 506, he concludes that his appeal
waiver is invalid as well.
But we have previously rejected this logic: appeal waivers remain valid even
when a defendant “argues that his waiver was not knowing and intelligent because he
had no reason to anticipate” a subsequent legal development. United States v. Bownes,
405 F.3d 634, 636 (7th Cir. 2005); accord United States v. Vela, 740 F.3d 1150, 1152, 1154
(7th Cir. 2014). True, a defendant may contend that an appeal waiver is invalid because
it was entered unknowingly or involuntarily, or without the district court taking the
plea in compliance with Rule 11 of the Federal Rules of Criminal Procedure. See United
States v. Cole, 569 F.3d 774, 776 (7th Cir. 2009). But “abundant case law” holds that
appeal waivers do not become invalid just because “the law changes in favor of the
defendant after sentencing.” Bownes, 405 F.3d at 636.
This conclusion is consistent with the principle that guilty pleas must be made
“voluntarily, knowingly, and intelligently, ‘with sufficient awareness of the relevant
circumstances and likely consequences.’” Bradshaw v. Stumpf, 545 U.S. 175, 183 (2005)
(quoting Brady v. United States, 397 U.S. 742, 748 (1970)). A plea is intelligently made
when the defendant understands at the time of his plea “not only the nature of the
charge … but also that his or her conduct actually falls within the charge.” United States
v. Olson, 880 F.3d 873, 877 (7th Cir. 2018) (quoting United States v. Frye, 738 F.2d 196, 199
(7th Cir. 1984) (alteration in original)). To meet this standard, the defendant is not
required to have perfect information. See, e.g., United States v. Graf, 827 F.3d 581, 585–86
(7th Cir. 2016). And this imperfect information can produce plea deals that, like any
contract, will still be knowing and intelligent despite “the risk of future changes in
circumstances” and an inability to foresee them. Bownes, 405 F.3d at 636.

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Both parties may manage this risk of a future change in circumstances in
negotiating the terms of the plea deal and appeal waiver, as occurred here. When
Crockett pleaded guilty, this court had already acknowledged a circuit split on the
meaning of “occasions.” See, e.g., Morris, 821 F.3d at 880, abrogated by Wooden, 142 S.Ct.
at 1068–69. Rather than pursue on appeal the chance of a favorable legal change to the
meaning of that word, Crockett bargained away his right to appeal in return for an
immediate benefit: the government’s offer to drop the body armor count and to
recommend that he receive the minimum ACCA sentence. By receiving these benefits in
return for his plea deal, Crockett gave up the right to mount a challenge to his
conviction on appeal. Davila v. United States, 843 F.3d 729, 731–32 (7th Cir. 2016).
Crockett attempts to distinguish this precedent on appeal waivers in two ways,
but neither is persuasive. First, he argues that Wooden did not “change” the law; it
merely explained what the statute “had meant ever since [it] was enacted.” See Bousley,
523 U.S. at 625 (Stevens, J., concurring in part and dissenting in part). Therefore, he
concludes, his plea involved an invalidating “mutual mistake” about the law’s
meaning. Through his appeal waiver, however, Crockett bargained away the right to
argue that such a mistake occurred. See, e.g., Oliver v. United States, 951 F.3d 841, 844–45
(7th Cir. 2020).
Second, Crockett argues that some of this court’s cases upholding appeal waivers
in the face of legal developments are inapposite because they rely on Brady v. United
States, 397 U.S. 742 (1970). Brady stated that a guilty plea “intelligently made in the light
of the then-applicable law does not become vulnerable because later judicial decisions
indicate that the plea rested on a faulty premise.” Id. at 757. Bousley distinguished Brady
as concerning a defendant who had “misjudged the strength of the Government’s case
or the penalties to which” he was subject, 523 U.S. at 619, but who had known “the
nature of the charge against him.” Id. (quoting Brady, 397 U.S. at 756). Moreover, Bownes
did not rely on Brady. The distinction in Bousley—a case, which, importantly, did not
involve an appeal waiver—does not undercut the rationale of our case law regarding
the negotiability and enforceability of such waivers.
For the same reasons, an argument that the change in law rendered his plea not
voluntary (as opposed to unknowing) fails. See Vela, 740 F.3d at 1154. “A change in the
law after a defendant pleads guilty does not change the voluntariness of the plea at the
time it was entered and does not justify a defendant withdrawing his plea.” Grzegorczyk
v. United States, 997 F.3d 743, 748 (7th Cir. 2021), cert. denied, 142 S.Ct. 2580 (2022).

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Finally, for completeness we note that Crockett does not appear to argue that,
apart from the change-in-law, his plea was not knowing or voluntary. Federal Rule of
Criminal Procedure 11 “ensures that the defendant’s plea is knowing and voluntary.”
United States v. Schaul, 962 F.3d 917, 921 n.10 (7th Cir. 2020). Because Crockett did not
move to withdraw his plea in the district court, any review of it would be for plain
error. See United States v. Goliday, 41 F.4th 778, 782–83 (7th Cir. 2022). Although the
judge did not discuss the elements or factual bases of the charges, he confirmed that
Crockett had read the plea agreement, which elaborates on the factual bases for—and
states the elements of—the 18 U.S.C. § 922(g) offenses. The agreement also states that
Crockett is subject to the ACCA, stating that each of the six listed prior offenses was “a
violent felony or serious drug offense” and that the government would be able to prove
“beyond a reasonable doubt” that three of the prior offenses “occurred on three
different occasions.” Finally, Crockett, who has a high school equivalency degree,
signed the agreement below a line affirming: “My attorney has reviewed every part of
this agreement with me….” These circumstances show that the plea and the appellate
waiver are valid. See United States v. Polak, 573 F.3d 428, 432 (7th Cir. 2009) (no plain
error because “substitutes for a proper Rule 11 colloquy were in place,” such as
defendant’s high school education and review of plea agreement with attorney); United
States v. Driver, 242 F.3d 767, 771 (7th Cir. 2001).
B. Whether the Sentence Exceeds the Statutory Maximum
Crockett also attempts to avoid the appeal waiver by arguing that his 180-month
sentence was illegal because it was greater than the maximum for each of his illegal-
possession counts under 18 U.S.C. § 922(g). Crockett asserts that the plea did not
include facts showing that he committed his prior felonies on different occasions and
therefore it lacked a sufficient factual basis for the ACCA count. “The only support in
the record for imposing the ACCA enhanced penalties,” he insists, was his stipulation
that the offenses occurred on separate occasions.2 This stipulation, he concedes, might
have shown “that his offenses were committed sequentially” and satisfied this court’s
pre-Wooden law. But after Wooden, he asserts, the stipulation is insufficient. He relatedly
appears to argue that, after Wooden, the question whether prior offenses occurred on
different occasions is one of law, and therefore he could not stipulate to it. See Goliday,
41 F.4th at 785–86 (internal quotations marks omitted and citations omitted) (“Criminal
defendants…may not stipulate to legal conclusions in plea agreements.”).
2 The plea agreement also listed what the offenses were, when he was convicted, and in what cities.

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Once again, the appeal waiver precludes these arguments. Although the appeal
waiver contains an exception if a sentence exceeds the statutory maximum that applies
to his convictions, it blocks challenges to the factual or legal basis for those convictions.
In United States v. Carson, we held that arguments like the one Crockett makes are
“entirely circular” and do not defeat an appeal waiver. 855 F.3d 828, 831 (7th Cir. 2017)
(quoting United States v. Worthen, 842 F.3d 552, 555 (7th Cir. 2016)). It is not possible to
rule that Crockett’s punishment exceeds the statutory maximum for his non-ACCA
convictions without first deciding that Crockett was not subject to an enhanced sentence
under the ACCA. This analysis, however, would require the court to reach the merits of
Crockett’s appeal, in violation of the valid appeal waiver. We have held that we will not
consider these arguments. Worthen, 842 F.3d at 555.
We conclude with two final matters. First, because the appeal waiver prevents us
from considering the merits, we do not address Crockett’s merits-based argument that
this court should overrule Elliott, which held that a district judge may determine
whether prior convictions have been committed on occasions different from one
another. 703 F.3d at 381. Second, we deny Crockett’s motion to supplement the record
with the charging documents and police reports related to his prior felonies. These
records would be pertinent only if the appeal waiver were invalid.
We therefore dismiss the appeal.

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