United States of America v. Dennis McKay

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 24-2015
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
DENNIS MCKAY,
Defendant-Appellant.
____________________
Appeal from the United States District Court for the
Northern District of Illinois, Eastern Division.
No. 1:17-cr-00729-1 — Andrea R. Wood, Judge.
____________________
ARGUED JANUARY 30, 2026 — DECIDED MAY 20, 2026
____________________
Before BRENNAN, Chief Judge, and ROVNER and HAMILTON,
Circuit Judges.
HAMILTON, Circuit Judge. Defendant-appellant Dennis
McKay challenges one condition of his future supervised
release. Before and during his sentencing hearing, defendant
did not affirmatively object to that condition. When the
district court specifically asked the parties to justify the
condition, however, defense counsel said it was unwarranted.
The government argues that defendant has waived his legal

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2 No. 24-2015
arguments on appeal by not raising them before the district
court. We conclude that defendant lodged an adequate
objection to the condition by saying on the record that it was
unwarranted. And Yee v. City of Escondido, 503 U.S. 519 (1992),
and our own precedents on preserving sentencing issues for
appeal allow a party to make new arguments on appeal that
support a properly preserved challenge. Defendant’s legal
challenges to the supervised release condition at issue are not
waived.
The challenged condition would require defendant to
notify third parties of a “risk” he poses as determined by a
probation officer. In other cases, this court has vacated that
same condition as impermissibly vague. Both parties agree
that if we reach the merits of defendant’s argument, remand
is appropriate. We therefore vacate the challenged supervised
release condition and remand the case to the district court for
further proceedings.
I. Factual & Procedural Background
In June 2023, defendant Dennis McKay pled guilty to
several charges: three counts of Hobbs Act robbery affecting
commerce in violation of 18 U.S.C. § 1951(a) and one count of
discharging a firearm in connection to a crime of violence in
violation of 18 U.S.C. § 924(c)(1)(A)(iii). In his plea agreement,
defendant also stipulated to having commiĴed four
additional robberies and to possessing a firearm as a felon.
Before defendant’s sentencing hearing, the U.S. Probation
Office for the Northern District of Illinois prepared a
Presentence Investigation Report. The PSR recommended the
following condition, Special Condition 13, of supervised
release:

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No. 24-2015 3
If the probation officer determines that you pose
a risk to another person (including an
organization or members of the community),
the probation officer may require you to tell the
person about the risk, and you must comply
with that instruction. Such notification could
include advising the person about your record
of arrests and convictions and substance use.
The probation officer may contact the person
and confirm that you have told the person about
the risk.
As justifications for the recommended conditions, the PSR
cited compliance with statutory factors of deterrence,
protection of the public, providing the defendant with
effective correctional treatment, and the probation officer’s
duty to stay informed of defendant’s conduct and
compliance. Defendant McKay then filed his sentencing
memorandum, which contained wriĴen objections to two
other conditions of supervised release but no objection to
Special Condition 13.
At defendant’s sentencing hearing, the district judge
confirmed with his counsel that he had reviewed the PSR with
defendant and confirmed directly with defendant that he had
reviewed the PSR with his counsel. Defendant did not lodge
any further objections or corrections to the PSR. The district
judge sentenced defendant to a prison term of 240 months
followed by three years of supervised release.
The judge then reviewed the conditions of supervised
release. When the judge reached Special Condition 13, she
asked the parties and probation officer about “any particular
concern with respect to third-party risk.” The probation

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4 No. 24-2015
officer responded that, given the charged crimes and past
crimes of violence, defendant’s prior convictions “might be
something that needs to be known” by future employers or
supervisors. The government then reiterated that the violent
nature of defendant’s offenses warranted the condition.
Defense counsel responded, “Judge, other than the offenses at
issue, that there’s no real background or the offenses we
discussed in sentencing, including the prior stuff, there’s no
consistent threat of violence towards others.”
The district judge decided to impose Special Condition 13,
but she added that she would change the condition if she had
“any reason to think that a probation officer is abusing this in
requiring disclosure of Mr. McKay’s situation in a way that
makes it hard for him to be a productive person when he’s
released from custody.” The judge also observed, “I’ll just
note [Special Condition 13] wasn’t objected to initially. I did
want to give defense counsel a chance to respond after I had
heard more from Probation and the government.” This appeal
followed, challenging only the validity of Special Condition
13 of supervised release.
II. Analysis
A. Waiver
We first address whether defendant McKay has waived his
challenge to Special Condition 13 altogether by failing to
make a sufficient objection to the condition in the district
court. The government argues that defendant made a
strategic and intentional choice to forgo objecting to Special
Condition 13 before sentencing, and that the objection made
by defense counsel when asked by the district court was not
enough to prevent waiver from applying here. We first

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No. 24-2015 5
consider whether the record indicates that defendant made a
sufficient general objection to Special Condition 13 and then
more specifically whether the recorded objection was
sufficient to preserve the legal arguments that defendant
advances on appeal. The answer to both questions is yes.
As a general maĴer, an issue is preserved for appellate
review when a party timely informs the court of “the party’s
objection to the court’s action and the grounds for that
objection.” Fed. R. Crim. P. 51(b). Failure to make a
contemporaneous objection can result in waiver or forfeiture
of the argument on appeal. The government argues that
defendant McKay waived his challenge to Special Condition
13. Waiver “occurs when a defendant intends (by words or
actions) to relinquish a known right.” United States v. Hunt,
930 F.3d 921, 924 (7th Cir. 2019). We ordinarily evaluate
waiver within the context of each case’s specific facts and
construe waiver principles liberally in favor of the defendant
in a criminal case. See United States v. Butler, 777 F.3d 382, 387
(7th Cir. 2015).
In United States v. Flores, this court sought to clarify our
existing case law on when a failure to object to a supervised
release condition amounts to waiver and thereby forecloses
appellate review. 929 F.3d 443 (7th Cir. 2019).1 “In the context
of supervised release conditions, evidence of a strategic
reason not to object in the district court is a sufficient, but not
a necessary, ground on which to find waiver, because it
1 Before the Flores opinion was issued to sort out inconsistencies in our
case law on waiver of objections to supervised release conditions, that
panel circulated the opinion under Circuit Rule 40(e). No active judge
voted to rehear the case en banc. Flores, 929 F.3d at 450 n.1.

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6 No. 24-2015
reflects an intentional decision on the defendant’s part.” Id. at
448.
The defendant in Flores had the opportunity to object to
the supervisory release condition at issue in the PSR before
sentencing but did not do so. Id. at 446. At the beginning of
the sentencing hearing, the defendant did not voice any
further objections to the PSR. She also said that she had
reviewed it with her counsel. Also, after the district court
announced the length of the prison sentence and supervised
release term, defense counsel affirmatively waived the need
for the court to explain the reasons for each of the supervised
release conditions. Id. at 446–47. We found that the
combination of advance notice of the condition, filing of
wriĴen objections to the PSR that did not include objections
to the condition at issue, the lack of objection, and the
affirmative waiver of the reading and explanation of the
supervised release conditions at the defendant’s sentencing
hearing amounted to “a deliberate and informed decision”
not to object, waiving the challenge being raised on appeal. Id.
at 448–50.
As the government points out, the facts before us are
similar to Flores in many ways, including the advance notice
of the supervised release conditions and defendant’s
objections to other conditions, but not Special Condition 13,
before and at the beginning of his sentencing hearing.
But unlike in Flores, defense counsel here was asked
directly about the condition when the district judge reviewed
the supervisory conditions. Counsel then voiced his general
objection to Special Condition 13. He said that “there’s no
consistent threat of violence towards others” that would
justify imposing the condition. As we understand what

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No. 24-2015 7
happened, the defense raised a general objection, albeit an
imprecise one, and the district court did not press for further
elaboration. The district judge noted that, although the
defense had not initially objected to Special Condition 13, she
had wanted to hear from the defense after the probation
officer and government offered reasons for the condition. And
after hearing from all parties, the district court chose to
impose the condition. This key factual difference, combined
with the absence of any record evidence or other indication
that defendant’s prior silence was a strategic choice, is
sufficient to rebut the government’s waiver argument.
Still, the government argues that defendant’s legal
arguments on appeal are waived because they were not made
more specifically in the district court. Defendant’s only
objection to Special Condition 13 at his sentencing hearing
was that the condition was unwarranted because his
background and the pending charges did not establish a
“consistent threat of violence towards others.” On appeal,
defendant challenges Special Condition 13 on vagueness,
First Amendment, and non-delegation grounds. The
government says that this difference between defendant’s
factual argument in the district court and his legal arguments
on appeal means that his legal arguments are waived.
This argument gives us occasion to reaffirm our approach
to an issue this circuit sees frequently: which new arguments
are deemed waived or forfeited in criminal cases when they
were not first raised and preserved in the district court?
On this issue, we are guided by Yee v. City of Escondido, 503
U.S. 519 (1992). There, plaintiffs alleged that a local rent
control ordinance effected a taking of property in violation of
the Fifth Amendment. Id. at 523. Though the plaintiffs

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8 No. 24-2015
“unquestionably raised a taking claim in the state courts,”
they raised on appeal a new theory, a regulatory taking
argument in addition to the physical taking argument already
made in the state courts. Id. at 534–35. The Court
distinguished between claims and arguments: “Once a
federal claim is properly presented, a party can make any
argument in support of that claim; parties are not limited to
the precise arguments they made below.” Id. at 534. In other
words, because the plaintiffs had preserved the Fifth
Amendment taking claim, they could make different
arguments as to how the ordinance constituted a taking.
Following the guidance in Yee, this court has repeatedly
recognized in both civil and criminal cases that “no rule
prohibits appellate amplification of a properly preserved
issue.” Lawson v. Sun Microsystems, Inc., 791 F.3d 754, 761 (7th
Cir. 2015); accord, United States v. Otradovec, 72 F.4th 794, 796
(7th Cir. 2023) (same); United States v. Billups, 536 F.3d 574, 578
(7th Cir. 2008) (similar); Bew v. City of Chicago, 252 F.3d 891,
895–96 (7th Cir. 2001) (addressing new argument on appeal
that “supports a claim made before the district court” and
“grow[ing] out of the facts presented to the district court”).
For example, in Billups, the defendant made the general
claim that his prior false imprisonment conviction should not
be classified as a crime of violence. 536 F.3d at 578. In the
district court, this argument centered on the elements of the
false imprisonment offense in Wisconsin state court jury
instructions. On appeal, however, the defendant relied on a
different statutory definition to support his claim. The
government argued that the statutory definition was not
before the district court, so defendant’s new argument on
appeal was forfeited. This court rejected that argument,

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No. 24-2015 9
instead finding the new definition to be “a new twist on [the
same] argument based upon additional authority on appeal.”
Id. Similarly here, defendant McKay may offer new “twists”
and further authority on his objection to Special Condition 13
in the district court.
This court’s precedents on waiver and forfeiture issues in
criminal cases can at times draw very fine distinctions. For
example, in United States v. Anderson, we said that a
defendant’s vagueness challenge to a supervised release
condition on appeal had been waived because at sentencing
he objected to the condition only as unnecessary. 948 F.3d 910,
911 (7th Cir. 2020). And in United States v. Tjader, we treated a
defendant’s challenges to multiple supervisory conditions as
waived, even though he had objected to two of them before
the district court, because he asserted new grounds on appeal.
927 F.3d 483, 484–85 (7th Cir. 2019).
But in both cases, we found waiver based on the principles
we articulated in Flores: that when a defendant has advance
notice and an opportunity to object, but makes only strategic
objections while intentionally forgoing others, appellate
review of a new argument has been waived. Anderson, 948
F.3d at 911–12; Tjader, 927 F.3d at 485. In other words, those
opinions did not address the difference between waiver of
claims and waiver of arguments articulated by Yee v. City of
Escondido. Today, we try to make clear that Yee guides us to
examine whether a new legal argument is advanced on
appeal that stems from the same underlying claim advanced
before the district court.
Deciding when appellate arguments constitute more than
a new “twist” on arguments made to the district court is
admiĴedly a maĴer of degree. Arguments that raise new

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10 No. 24-2015
factual and evidentiary arguments, where a reviewing court
would benefit from the trial court’s analysis in the first
instance, are not encompassed by Yee. See Arnold v. United
Airlines, Inc., 142 F.4th 460, 474–75 (7th Cir. 2025) (waiver
applied; plaintiff argued new theory of employer retaliation
on appeal); Packer v. Trustees of Indiana Univ. Sch. of Med., 800
F.3d 843, 848–49 (7th Cir. 2015) (waiver applied; plaintiff
raised new factual arguments on appeal and relied upon
evidence not properly cited before district court); Puffer v.
Allstate Insurance Co., 675 F.3d 709, 718–19 (7th Cir. 2012)
(waiver applied; intervenors argued new theory of
discrimination on appeal). But defendant McKay’s arguments
on appeal raise pure questions of law. They do not fall into
this category, so he is not barred by waiver from advancing
them before us.
B. Special Condition 13
Having determined that defendant objected to Special
Condition 13 and that his legal arguments on appeal are not
waived, we apply a de novo standard of review. See United
States v. Russell, 140 F.4th 430, 438 (7th Cir. 2025), citing United
States v. Sandidge, 863 F.3d 755, 758 (7th Cir. 2017).
On the merits, defendant’s challenges to Special Condition
13 are comparatively straightforward. Defendant challenges
the supervisory condition on vagueness, non-delegation, and
First Amendment grounds. We need to reach only his
vagueness argument. Both parties agree that, absent waiver, a
limited remand of Special Condition 13 is warranted to clarify
the meaning of several of its terms. Accordingly, we remand
so the district court can reconsider and, as appropriate,
modify and/or further explain the necessity and scope of
Special Condition 13.

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No. 24-2015 11
Recall that Special Condition 13 allows the probation
officer, if he believes the defendant “pose[s] a risk to another
person (including an organization or members of the
community),” to require the defendant himself to disclose
that risk to the affected person. The probation officer may
then contact that person to verify whether the defendant has
disclosed the risk. During sentencing, the district court did
not define what “risk” means within this condition and did
not specify, beyond the general language in the PSR, which
“person[s]” the probation officer may compel the defendant
to notify.
“A condition of supervised release is unconstitutionally
vague if it would not provide a person of reasonable
intelligence with sufficient notice as to the condition’s
requirements.” United States v. Shannon, 851 F.3d 740, 744 (7th
Cir. 2017). The “principal concern” underlying the vagueness
doctrine is that a defendant might “unknowingly run[] afoul
of a legal requirement.” Id.
This court has previously vacated almost identically
phrased supervisory release conditions, concluding that the
conditions’ undefined terms were impermissibly vague.
United States v. Thompson, 777 F.3d 368, 379 (7th Cir. 2015);
United States v. Kappes, 782 F.3d 828, 849 (7th Cir. 2015); United
States v. Guidry, 817 F.3d 997, 1010 (7th Cir. 2016); United States
v. Bickart, 825 F.3d 832, 841–42 (7th Cir. 2016); United States v.
Canfield, 893 F.3d 491, 495 (7th Cir. 2018); United States v. Greco,
938 F.3d 891, 897 (7th Cir. 2019); Russell, 140 F.4th at 438. For
the reasons discussed in those opinions, we vacate Special
Condition 13 and remand to the district court “to define with
greater specificity the identities or categories of individuals

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12 No. 24-2015
and the types of risks to which notification conditions such as
this would apply.” Canfield, 893 F.3d at 495.
We therefore VACATE Special Condition 13 and
REMAND for further proceedings consistent with this
opinion. In light of our precedents vacating this condition and
similarly worded ones, we urge probation offices throughout
this circuit, when they deem such a condition warranted, to
recommend it in concrete terms. We direct the Clerk’s Office
to distribute a copy of this opinion to each Chief Probation
Officer in this circuit.

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