United States of America v. JOSHUA M. DuPAGE

United States Court of Appeals
For the Seventh Circuit
Chicago, Illinois 60604
Argued November 15, 2023
Decided January 5, 2024
Before
DIANE S. SYKES, Chief Judge
MICHAEL B. BRENNAN, Circuit Judge
JOHN Z. LEE, Circuit Judge
No. 23-1009
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
JOSHUA M. DuPAGE,
Defendant-Appellant.
Appeal from the United States District
Court for the Central District of Illinois.
No. 18-CR-10014-001
James E. Shadid,
Judge.
O R D E R
Joshua DuPage pleaded guilty to possessing methamphetamine with intent to
distribute and possessing a firearm in furtherance of drug trafficking. The parties
agreed to a 156-month aggregate sentence. DuPage also agreed to waive his rights to
appeal his conviction and any resulting sentence. In exchange, the government
dismissed another firearm count, recommended that the sentence be concurrent with
DuPage’s state sentences, and withdrew a proposed enhancement linked to a prior state
methamphetamine conviction. The enhancement, if valid, would have led to a
combined 180-month mandatory minimum.
NONPRECEDENTIAL DISPOSITION
To be cited only in accordance with FED. R. A PP. P. 32.1

-- 1 of 5 --

No. 23-1009 Page 2
On appeal, DuPage argues for the first time that his plea agreement, including
his appeal waiver, was invalid because he received no consideration for it. In his view,
the enhancement on which the government relied was legally unsupportable and, thus,
the government’s withdrawal of it had no value. For this and other reasons, he asks that
we undo his plea under the plain-error standard. Based on this record, however, we
conclude that the district court did not plainly err by accepting DuPage’s guilty plea.
And, with the plea intact, DuPage’s agreement to waive his appeal rights requires the
dismissal of this appeal.
In 2018, DuPage was charged in a three-count indictment with distributing
methamphetamine, 21 U.S.C. §§ 841(a)(1), (b)(1)(B); possessing a firearm in furtherance
of drug trafficking, 18 U.S.C. § 924(c); and unlawfully possessing a gun as a felon,
id. § 922(g). The government filed a notice of enhancement under 21 U.S.C. § 851
because, it said, DuPage had a prior conviction for a “serious drug felony” as defined in
21 U.S.C. § 802(57): a 2009 Illinois conviction for aggravated participation in
methamphetamine manufacturing, 720 ILCS 646/15 (2009). With the enhancement,
DuPage faced a mandatory minimum 15 years in prison: 10 for the § 841 offense plus 5
for the § 924(c) offense. 21 U.S.C. § 841(b)(1)(B). Without it, the minimum was 10 years:
5 for the § 841 offense plus 5 for the § 924(c) offense. Id. Either way, due to the 924(c)
offense, the maximum term of imprisonment was life. In addition, he faced up to 10
years’ imprisonment for the § 922(g) offense, which could run concurrent with or
consecutive to the drug count.
Against this backdrop, the parties entered a plea agreement for a binding
sentence under Rule 11(c)(1)(C) of the Federal Rules of Criminal Procedure. If accepted
by the district court, the plea required a 13-year prison term (156 months). In exchange
for DuPage’s willingness to plead guilty, the government agreed to withdraw the
enhancement notice, dismiss the § 922(g) charge, and recommend that the sentence run
concurrently with any uncharged state sentence. As part of this deal, DuPage also
agreed to waive his rights to appeal the conviction and sentence.
After a magistrate judge conducted a colloquy and the district judge accepted the
plea, DuPage moved to withdraw it—but not on the grounds raised today. Rather, he
argued that counsel had not timely let him see some discovery materials. The district
court denied the motion, ruling that DuPage had entered the plea knowingly and
voluntarily. Along the way, DuPage’s counsel mentioned that he and DuPage had
discussed a potential challenge to the enhancement if the case proceeded to trial, and
that counsel was uncertain about the odds of success. Again, however, DuPage did not

-- 2 of 5 --

No. 23-1009 Page 3
press this as a ground for invalidating the plea. The court adopted the plea agreement
and sentenced DuPage to 13 years in prison.
DuPage now asks us to set aside his plea, claiming that he entered the plea
agreement unknowingly and involuntarily. And if his plea is void, he contends, so too
is his appeal waiver. See United States v. Nulf, 978 F.3d 504, 506 (7th Cir. 2020) (holding
an appeal waiver “stands or falls with the underlying agreement and plea”).
In support, DuPage offers two theories for invalidating his plea: one based on
Rule 11, and the other based on contract principles. But because DuPage did not raise
these arguments in the district court, we review for plain error. See United States v.
Williams, 946 F.3d 968, 971 (7th Cir. 2020). Under this standard, DuPage must show (1)
that the district court committed an error, (2) that is clear or obvious, (3) that affects his
substantial rights, (4) and that seriously diminishes the fairness, integrity, or reputation
of judicial proceedings. Id.
DuPage begins by asserting that his plea colloquy violated Rule 11(b)(1)(I)
because, he says, the judge did not correctly inform him of the mandatory minimum
sentence that could be imposed. But this contention fails for two reasons. First, in the
colloquy, the magistrate judge did tell DuPage of the correct 5-year minimum for the
federal methamphetamine offense. The judge then added the conditional statement that
DuPage objects to now: If DuPage had a prior serious drug conviction as defined by
federal law, then the mandatory minimum sentence of imprisonment would increase to
10 years. This was correct. See 21 U.S.C. §§ 841(a)(1), (b)(1)(B). We have not found any
case holding that a conditional statement like this violates the judge’s duty to recite the
correct potential penalties. Thus, it is not obvious that any Rule 11 error occurred, even
if we credited DuPage’s argument that the enhancement would have been invalid.
Second, to demonstrate that a putative Rule 11 error affected his substantial
rights, DuPage must show a reasonable probability that, but for the judge’s incorrect
statement of the applicable mandatory minimum, he would not have pleaded guilty.
See United States v. Goliday, 41 F.4th 778, 786 (7th Cir. 2022). On this record we see no
real probability that DuPage would have backed out of the agreement if the judge had
not informed him of the potential impact of the sentencing enhancement. DuPage may
have dreaded the potential applicability of the enhancement, but any such fear did not
stem from the magistrate judge’s recitation of penalties.

-- 3 of 5 --

No. 23-1009 Page 4
Next, relying on contract principles, DuPage invokes United States v. De La Torre,
940 F.3d 938 (7th Cir. 2019), and argues that he may undo his plea because the parties
mistakenly assumed his prior drug conviction could be used to enhance his sentence.
Given that kind of mistake, he says, the government’s agreement to withdraw the
enhancement was “no concession at all” and was inadequate consideration for the plea
agreement.
But, in general, defendants cannot invalidate plea agreements based on
unanticipated legal developments. See, e.g., United States v. McGraw, 571 F.3d 624, 631
(7th Cir. 2009). And nowhere have we held that a defendant’s prior conviction of an
Illinois methamphetamine offense does not qualify as a “serious drug felony” under
§ 841(b)(1)(B). Still, DuPage argues that the district court should have plainly known
that this was the case. Yet his argument regarding this purported misfit depends on
nuanced textual differences between the state and federal methamphetamine statutes,
discussions in Illinois appellate decisions, and out-of-circuit appellate decisions. The
conclusion he urges now hardly seems plain.
In any event, we need not and do not resolve this open question. For even if
DuPage were right about the validity of the dropped enhancement, there was ample
other consideration for his plea.
To start, the government agreed to dismiss a § 922(g) charge that would have
added a felony to his record. And if DuPage had timely pleaded guilty without this
agreement and without the enhancement, then the § 922(g) charge also would have
increased his guidelines range from 130–147 months (70–87 for the un-enhanced § 841
count plus 60 consecutive months for the § 924(c) count) to 144–165 months (84–105 for
the § 841 and § 922(g) counts plus 60 consecutive months for the § 924(c) count). And
even those figures may be too generous: Had DuPage gone to trial, he would not have
received a three-level reduction for acceptance of responsibility, so he would have faced
170–197 months (110–137 for the § 841 and § 922(g) counts plus 60 consecutive months
for the § 924(c) count). Measured by those standards, agreeing to a fixed term of 156
months made sense. Plus, the government agreed to recommend that the federal
sentence be served concurrently to any state sentence.
DuPage’s reliance on De La Torre is misplaced. In De La Torre, defendants
Chapman and Rush showed it was reasonably probable they would not have entered
their plea agreements but for the mandatory life sentences they each believed they faced
because of (invalid) enhancements. 940 F.3d at 950, 53. For Chapman, the record was

-- 4 of 5 --

No. 23-1009 Page 5
“abundantly clear” that he agreed to a 25-year sentence only because he believed
mandatory life in prison was the alternative. Id. at 949–50. And for both defendants, the
sentencing judge voiced concern at the length of the binding sentences, labeling them
“greater than necessary.” Id. at 950, 53. Here, by contrast, the record is not at all clear
that DuPage would not have entered the plea but for the enhancement. Indeed, the
guidelines calculations without the enhancement make his decision look reasonable.
And nothing here suggests the sentencing judge thought the binding term of
imprisonment too high. In sum, valuable consideration apart from the withdrawn
enhancement supported this plea deal—a prospect that our opinion in De La Torre did
not examine.
Finally, for what it is worth, DuPage’s plea agreement, colloquy, and discussions
at sentencing all reflect that he and counsel were aware that the enhancement might not
apply and intentionally bargained around the legal uncertainty. Indeed, DuPage’s plea
agreement provided that “[i]f the defendant has a prior serious drug conviction” and
the § 851 notice were not withdrawn, then he would receive an enhanced sentence.
Likewise, at the colloquy, the magistrate judge said the enhancement would apply only
“if you have a prior serious drug conviction.” The same goes for counsel’s on-the-record
statements of uncertainty about the enhancement. Such language cuts against DuPage’s
assertion that all parties were sure he would receive an enhancement without the deal.
See United States v. Chapa, 602 F.3d 865, 868–69 (7th Cir. 2010) (no mutual mistake where
conditional language in agreement left “no doubt” that defendant considered potential
that provision would not apply).
We have repeatedly stressed that a major purpose of plea agreements is to
allocate risks about legal and factual uncertainty; when the parties have made those
allocations, we are loathe to interfere. See, e.g., Oliver v. United States, 951 F.3d 841, 845
(7th Cir. 2020); United States v. Bownes, 405 F.3d 634, 636 (7th Cir. 2005). To be sure,
DuPage contends that the record does not make clear why counsel was uncertain the
enhancement would apply; counsel may have had different reasons than the ones
pressed today, and thus may not have appreciated the true risks and benefits of the
deal. But if the record is unclear on this point, that does not mean DuPage wins; it
means only that DuPage cannot carry his burden to show the plainness of any error.
In sum, DuPage provides no valid grounds to nullify his plea or his plea
agreement. And, because we uphold the plea, his agreement to waive his rights to
appeal also stands. This appeal is DISMISSED.

-- 5 of 5 --