Dennis Wilson v. United States of America

United States Court of Appeals
For the Seventh Circuit
Chicago, Illinois 60604
Argued June 4, 2025
Decided June 13, 2025
Before
MICHAEL B. BRENNAN, Circuit Judge
MICHAEL Y. SCUDDER, Circuit Judge
THOMAS L. KIRSCH II, Circuit Judge
No. 24-1708
DENNIS WILSON,
Petitioner-Appellant,
v.
UNITED STATES OF AMERICA,
Respondent-Appellee.
Appeal from the United States District
Court for the Southern District of
Indiana, Indianapolis Division.
No. 1:21-cv-00178-JRS-CSW
James R. Sweeney II,
Judge.
O R D E R
On appeal from the denial of his motion under 28 U.S.C. § 2255, Dennis Wilson
contends that his federal convictions in 2019 for sexual exploitation of children should
be vacated because his lawyer provided ineffective assistance during plea negotiations.
Wilson, however, offers nothing to suggest that he would have demanded a trial absent
counsel’s alleged deficient performance, so he cannot shoulder his burden to establish
prejudice under Strickland v. Washington, 466 U.S. 668, 687 (1984). Accordingly, we
affirm.
NONPRECEDENTIAL DISPOSITION
To be cited only in accordance with FED. R. A PP. P. 32.1

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No. 24-1708 Page 2
I
The government charged Wilson with five counts of sexual exploitation of a
child, see 18 U.S.C. § 2251(a), (e), and one count of possessing child pornography,
see 18 U.S.C. § 2252(a)(4)(B), (b)(2). Suffice it to say that Wilson’s alleged crimes were
atrocious, and the evidence of his guilt substantial.
Wilson negotiated a pre-indictment plea agreement. He agreed to plead guilty to
the five counts of sexual exploitation of a child in exchange for the government
dismissing the remaining child pornography charge. The parties stipulated that Wilson
had a 1998 Indiana conviction for sexual misconduct with a minor. This prior offense
exposed Wilson to a mandatory minimum of 25 years and a maximum of 50 years in
prison on each count.
But the parties also labored under the impression, though not expressly noted in
the plea agreement, that Wilson’s prior Indiana conviction triggered a mandatory life
sentence under 18 U.S.C. § 3559(e) and that the government would have pursued this
sentence if Wilson chose to go to trial. Believing this mandatory life sentence was
something the parties could bargain away—it is not, see United States v. Cieslowski,
410 F.3d 353, 363 (7th Cir. 2005)—Wilson and the government ultimately agreed to a
plea agreement pursuant to Federal Rule of Criminal Procedure 11(c)(1)(C) with a
binding sentence of 35–50 years’ imprisonment and a lifetime of supervised release.
The district court accepted the Rule 11(c)(1)(C) agreement and calculated the
imprisonment range under the Sentencing Guidelines to be 360 to 3,000 months.
Neither party objected to this calculation. The court then sentenced Wilson—then 46
years old—to concurrent terms of 480 months in prison on each count and a lifetime of
supervised release.
Just under a year later, Wilson filed a motion under 28 U.S.C. § 2255 to vacate his
convictions on the ground that he received ineffective assistance of counsel because his
lawyer negotiated the plea based on an erroneous view of the law. Citing our decision
in United States v. Skaggs, 25 F.4th 494, 500 (7th Cir. 2022), the government
acknowledged there had been a “substantial error” in the plea negotiations: Wilson was
never in jeopardy of receiving a mandatory life sentence because his 1998 state
conviction for sexual misconduct with a minor did not correspond to any qualifying
“Federal sex offense” under 18 U.S.C. § 3559(e). But the government nevertheless
opposed post-conviction relief, arguing that Wilson’s lawyer should not have been
expected to make this argument because it was novel at the time and, regardless, it
would not have changed the outcome.

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No. 24-1708 Page 3
The district court questioned whether Skaggs barred a mandatory life sentence
but concluded that, even if it did, Wilson’s claim fell short. First, Wilson failed to
establish prejudice, as there was no indication he would have insisted on going to trial
had he known that a mandatory life sentence was off the table, and it was not a valid
theory of prejudice to argue that counsel could have negotiated a better plea deal absent
the error. Second, counsel’s advice to Wilson to accept the plea agreement was
objectively reasonable because the legal issues were debatable, and Wilson still faced a
possible de facto life sentence: at the highest end of the advisory guidelines range, five
consecutive maximum sentences would yield a total term of over 100 years’
imprisonment.
Wilson appealed, and we granted him a certificate of appealability to address
“whether counsel was ineffective in plea negotiations—specifically, for not recognizing
that Wilson’s prior conviction would not have subjected him to a mandatory life
sentence under 18 U.S.C. § 3559(e).”
II
To succeed on his claim for ineffective assistance of counsel, Wilson must show
that his lawyer’s performance was objectively unreasonable and prejudiced his defense.
See Strickland, 466 U.S. at 687–88. We review the district court’s denial of a § 2255
motion de novo. See Pettis v. United States, 129 F.4th 1057, 1062 (7th Cir. 2025).
This case is resolved on the prejudice element. On appeal, Wilson insists that he
would have gone to trial if his lawyer had correctly advised him of the maximum
penalty he faced and made clear that a mandatory life sentence was not legally
authorized. Under this theory, to establish prejudice Wilson must point to
“contemporaneous evidence,” Lee v. United States, 582 U.S. 357, 369 (2017),
demonstrating a “reasonable probability that, but for counsel’s errors, he would not
have pleaded guilty and would have insisted on going to trial,” id. at 364–65 (quoting
Hill v. Lockhart, 474 U.S. 52, 59 (1985)).
But Wilson offers only a bare and unsworn assertion to this effect, and such
unsupported allegations do not suffice to establish prejudice. See Hutchings v. United
States, 618 F.3d 693, 697 (7th Cir. 2010). He does not identify any statements during plea
negotiations, the change of plea hearing, or the sentencing hearing suggesting that the
risk of a mandatory life sentence was the only thing standing in the way of him
demanding a trial. Indeed, no such statements appear in the record. “Courts should not
upset a plea solely because of post hoc assertions from a defendant about how he would
have pleaded but for his attorney's deficiencies.” Lee, 582 U.S. at 369. And post hoc
assertions are all that Wilson offers.

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No. 24-1708 Page 4
On our review of the record, everything indicates that Wilson pleaded guilty
because it was the decision that made the most sense, even if his lawyer was mistaken
that going to trial risked a mandatory life sentence. Wilson knew he faced an effective
life sentence no matter what—he concedes that the top end of the sentencing range
amounted to 250 years’ imprisonment. And his prospects at trial were grim. Electronic
devices belonging to him clearly linked him to the offense conduct. Even more, at
sentencing his own lawyer acknowledged that, considering the aggravating factors in
this case, neither the statutory minimum nor the low end of the guideline range
supplied an appropriate sentence. In short, Wilson knew that going to trial would
almost certainly yield an outcome worse than what he achieved by pleading guilty, so
his counsel’s allegedly erroneous advice did not make going to trial any less enticing.
See Morales v. Boatwright, 580 F.3d 653, 663 (7th Cir. 2009).
Wilson has failed to carry his burden of showing there was a reasonable
probability that counsel’s alleged missteps affected his decision to plead guilty. We
therefore AFFIRM the district court’s judgment denying Wilson’s motion to vacate his
convictions.

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