Nathan Nissenbaum v. Chad Jennings

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 24-2162
NATHAN NISSENBAUM ,
Petitioner-Appellant,
v.
C HAD JENNINGS ,
Respondent-Appellee.
____________________
Appeal from the United States District Court for the
Northern District of Illinois, Eastern Division.
No. 22 C 7159 — Matthew F. Kennelly, Judge.
____________________
A RGUED M AY 15, 2025 — DECIDED A UGUST 5, 2025
____________________
Before R IPPLE, K IRSCH , and K OLAR , Circuit Judges.
K IRSCH , Circuit Judge. Nathan Nissenbaum was convicted
at trial in Illinois state court and sentenced to 14 years’ impris-
onment for aggravated criminal sexual assault, home inva-
sion, aggravated kidnapping, and aggravated domestic bat-
tery. In a post-trial motion, Nissenbaum alleged ineffective as-
sistance of counsel, claiming that his attorney failed to
properly advise him with respect to the potential mandatory
minimum sentence he faced and his realistic chances of

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2 No. 24-2162
prevailing at trial. If he had been adequately advised, Nissen-
baum claimed, he would have accepted a plea deal for a lesser
sentence. At the close of a three-day evidentiary hearing, the
trial court found that Nissenbaum failed to show ineffective
assistance of counsel, and the Illinois appellate court affirmed.
After exhausting the state court appellate process, Nissen-
baum filed a habeas petition in federal district court under 28
U.S.C. § 2254 in which he renewed his ineffective assistance
claims. The district court denied the petition, concluding that
the Illinois appellate court did not unreasonably apply federal
law in finding that Nissenbaum failed to show that he was
prejudiced by his counsel’s alleged deficient performance. We
agree and affirm.
I
A
Nathan Nissenbaum was arrested and ultimately con-
victed for beating and sexually assaulting a former girlfriend.
Nissenbaum and the victim, D.K., dated from December 2013
until November 2014. In January 2015, D.K. sought and re-
ceived an emergency order of protection against Nissenbaum
and, shortly thereafter, a mutual no-contact order was im-
posed. The following month, D.K., who worked as an escort,
received and accepted an online booking request from a new
client. Unbeknownst to D.K., the client was Nissenbaum, who
had booked the appointment under a false name.
Nissenbaum arrived at D.K.’s apartment at the appointed
time in disguise. D.K. says that Nissenbaum forced her to the
bed, handcuffed her, and held a gun to her head, threatening
to kill her. He then proceeded to duct tape her, strike her face
and body, choke her, and rape her. After assaulting D.K.,

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No. 24-2162 3
Nissenbaum removed the duct tape, announced that he was
going to kill himself, and walked into the bathroom. D.K. fled
the apartment and immediately called the police. Responding
officers found Nissenbaum in D.K.’s bathroom, bleeding from
razor blade cuts to his arms. He had also started a small fire
in the bathroom.
Police arrested Nissenbaum, and both he and D.K. were
transported to the hospital. In the ambulance, Nissenbaum
admitted to an officer that he had posed as a john to gain entry
to D.K.’s apartment and mentioned that the encounter “didn’t
go as planned.” The nurse who examined D.K. found marks
on her forehead, wrists, and shins, as well as a handprint on
her back. A sexual assault kit administered to D.K. confirmed
the presence of Nissenbaum’s DNA.
B
Nissenbaum was tried in state court on seven counts: two
counts of aggravated criminal sexual assault and two counts
of aggravated kidnapping, as well as one count each of home
invasion, aggravated domestic battery, and attempted aggra-
vated arson. Under Illinois law, aggravated criminal sexual
assault, home invasion, and aggravated kidnapping are all
Class X felonies that carry a minimum sentence of six years.
See 720 ILCS 5/11-1.30, 5/19-6, 5/10-2; 730 ILCS 5/5-4.5-25(a).
And a conviction for aggravated criminal sexual assault trig-
gers mandatory consecutive sentencing. 730 ILCS 5/5-8-
4(d)(2). This means that if convicted on the sexual assault
charge and any one of the other Class X offenses, Nissenbaum
faced a mandatory consecutive sentence of at least 12 years.
At his bench trial, Nissenbaum relied on a consent defense.
He testified that when he and D.K. were dating, they had

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4 No. 24-2162
regularly engaged in rough sex and consensual “rape play,”
which sometimes involved him surprising D.K. with a “vio-
lent rape sort of situation” when she wasn’t expecting it. Nis-
senbaum admitted to booking the appointment under a false
name and wearing a disguise but maintained that it was a
consensual encounter and that D.K. had not used their mutual
safe word to indicate that she wanted him to stop. He
acknowledged showing D.K. a gun—later revealed to be a BB
gun—but denied holding it to her head. As for the fire in the
bathroom, he claimed to have started it accidentally by knock-
ing over a candle. In the lead up to the trial, it was not clear
whether D.K. would cooperate with the prosecution, but she
ultimately testified against Nissenbaum. Though D.K. con-
firmed that the two of them had engaged in various “rape fan-
tasies” when they were dating, she denied that the assault in
February was one of these consensual encounters. The court
ultimately found Nissenbaum guilty of aggravated criminal
sexual assault, home invasion, aggravated kidnapping, and
aggravated domestic battery and sentenced him to 14 years’
imprisonment.
C
Nissenbaum was represented by attorney Michelle Trues-
dale both before and during his bench trial. After his convic-
tion, Nissenbaum retained new counsel and promptly filed a
post-trial motion alleging that Truesdale had rendered inef-
fective assistance of counsel. Specifically, Nissenbaum
claimed that Truesdale failed to inform him about the risk of
mandatory consecutive sentences before trial, leading him to
erroneously believe that he faced only a mandatory minimum
of 6—rather than 12—years if convicted on multiple counts.
He also claimed that Truesdale did not accurately advise him

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No. 24-2162 5
with respect to his chances of being acquitted at trial. If not for
this deficient performance, Nissenbaum said, he would have
accepted a plea deal for a lesser sentence rather than risk a
trial. The court accepted briefing from the parties and held a
three-day evidentiary hearing to investigate Nissenbaum’s
claims, during which the following evidence emerged.
Truesdale’s representation of Nissenbaum began in early
2015. Over the course of two years, she and Nissenbaum met
approximately 15 times and exchanged many emails discuss-
ing his case. Truesdale testified that as early as July 2015, she
discussed a possible plea to attempted aggravated arson with
Assistant State’s Attorney (ASA) Mary Innes. Negotiations
stalled, however, because Nissenbaum “wanted to work with
kids” and “didn’t want a felony on his record.”
According to Truesdale, she first broached the possibility
of consecutive sentencing with Nissenbaum during a Decem-
ber 2016 meeting in which they reviewed a copy of the charg-
ing document. Truesdale had placed sticky notes on the doc-
ument, notating each of the charged offenses with infor-
mation such as the elements of the offense, sentence ranges,
possible defenses, and whether sentences were consecutive.
Next to aggravated criminal sexual assault, Truesdale wrote:
“X, 6 to 30, + Consec.” Nissenbaum acknowledged that he saw
the annotated charging document but denied that Truesdale
explained consecutive sentencing to him at the meeting.
On March 23, 2017, Truesdale and Nissenbaum met again
to discuss his options, including the possibility of reopening
talks for a plea deal. Truesdale testified that she and Nissen-
baum again discussed the possibility of consecutive sentences
(which Nissenbaum denied). After this meeting, Truesdale
texted the new ASA assigned to the case, Jennifer Bagby, to

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6 No. 24-2162
explore a potential plea. Nissenbaum emailed Truesdale be-
fore ASA Bagby could respond, reiterating that while she
could explore a deal, he was “not ok with being a sex of-
fender” and “not ok with prison time.” He emailed Truesdale
again the following day to inquire about possibly delaying the
trial, remarking, “[i]f there is a chance that anything will give
me a shot at moving forward in a world without a felony, [my
parents] will support it and pay for it.”
On March 24, 2017, ASA Bagby responded to Truesdale’s
text message and said that she “could probably make an offer
on an agg[ravated] domestic battery for probation and an or-
der of protection,” noting that “the current administration
will have my back on this even though the victim will not be
happy.” At the evidentiary hearing, ASA Bagby explained
that she was eager to resolve the case because it involved se-
rious charges, and it was unclear at that time whether or not
D.K. would cooperate. She further clarified that this wasn’t an
actual offer for Nissenbaum to accept but rather the initiation
of a conversation about an offer. On March 28, Truesdale and
Nissenbaum met to discuss ASA Bagby’s proposal. Truesdale
recalled that Nissenbaum remained opposed to pleading to a
felony (aggravated domestic battery is a felony) and was in-
clined to move forward with a trial. Nissenbaum denied this,
saying that he just wanted more time to think about the offer,
which he thought would remain open until trial. On April 11,
after nearly two weeks had passed, ASA Bagby relayed that
she had finally met with D.K. and that any plea that did not
include a sex offense was now off the table.
The case proceeded to trial that summer. According to
Nissenbaum, Truesdale consistently expressed a strong belief
that he would be acquitted or convicted of only a minor,

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No. 24-2162 7
probation-eligible offense. Truesdale, on the other hand, tes-
tified that she accurately advised Nissenbaum of the strengths
and weaknesses of the state’s case and that her assessment of
his chances at trial varied over time based on the evidence she
thought the state might present and—in particular—whether
D.K. would cooperate. Partway through the trial, Nissen-
baum sent an email to Truesdale in which he remarked, “I
would just like my life back and no[t] find myself in prison for
the next 6–30.” Upon seeing this email, Truesdale emailed
ASA Bagby, asking whether the counts of aggravated crimi-
nal sexual assault carried mandatory consecutive sentences.
Truesdale later testified that she only reached out to ASA
Bagby because she was away from her case file at the time and
wanted quick confirmation. After ASA Bagby responded to
confirm that the sentences were consecutive, Truesdale re-
plied to Nissenbaum’s email, noting that he faced a potential
12 (not 6) year minimum. Nissenbaum says this was the first
time he was informed that he was facing a potential minimum
sentence of 12 years.
At the close of the evidentiary hearing, the trial court con-
cluded that, despite some ambiguity in the record, Nissen-
baum had not shown ineffective assistance of counsel. The
court found that, contrary to his assertions, Nissenbaum was
reasonably informed of his sentencing situation as well as his
chance of prevailing at trial. Moreover, even if Truesdale’s
performance had been deficient, the court concluded that Nis-
senbaum would not have been prejudiced because he would
have refused to accept a plea regardless. The Illinois appellate
court affirmed, finding that Nissenbaum failed to establish
that he was prejudiced by any alleged deficiencies in Trues-
dale’s performance. The Illinois Supreme Court denied Nis-
senbaum’s petition for leave to appeal. Having exhausted the

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8 No. 24-2162
state appellate process, Nissenbaum filed a habeas petition in
federal district court under 28 U.S.C. § 2254, claiming a viola-
tion of his Sixth Amendment rights. The district court denied
his petition, and this appeal followed.
II
We review a district court’s denial of a habeas petition de
novo. Woolley v. Rednour, 702 F.3d 411, 420 (7th Cir. 2012). But
the Antiterrorism and Effective Death Penalty Act of 1996
(AEDPA) requires us to give substantial deference to “the
judgment of a State court.” 28 U.S.C. § 2254(d). When a claim
has been adjudicated on the merits in a state court proceeding,
AEDPA bars federal habeas relief unless the state court adju-
dication “resulted in a decision that was contrary to, or in-
volved an unreasonable application of, clearly established”
Supreme Court precedent or “resulted in a decision that was
based on an unreasonable determination of the facts in light
of the evidence presented in the State court proceeding.” Id.
§ 2254(d)(1) & (2). In this posture, we also defer to state court
factual findings, which are presumed correct unless a peti-
tioner rebuts them by clear and convincing evidence. Id.
§ 2254(e)(1).
To prevail on an ineffective assistance of counsel claim, a
defendant must show (1) that his counsel’s performance was
deficient and (2) that this “deficient performance prejudiced
the defense.” Strickland v. Washington, 466 U.S. 668, 687 (1984).
Because a defendant must satisfy both the prejudice and per-
formance prongs, a court considering an ineffective assistance
claim need not “address both components of the inquiry if the
defendant makes an insufficient showing on one.” Id. at 697.

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No. 24-2162 9
A
The state trial court found that Nissenbaum failed to
demonstrate both deficient performance and prejudice, but
the state appellate court affirmed only on prejudice grounds,
leaving the performance prong of Nissenbaum’s Strickland
claim unaddressed. The parties disagree about how this af-
fects our standard of review. Our circuit interprets § 2254(d)
as directing federal courts to review only a single state court
decision, “[u]nless a state-court opinion adopts or incorpo-
rates the reasoning of a prior opinion.” Woolley, 702 F.3d at
421. When, as here, a lower state court ruled on both Strickland
prongs but the final state court to adjudicate the claim ad-
dressed only one, we have held that our deferential review
under § 2254(d) extends only to the prong adjudicated by the
last state court, meaning we review the remaining prong de
novo. Thomas v. Clements, 789 F.3d 760, 766–67 (7th Cir. 2015).
The State asks us to overrule Thomas and hold that when
the last state court to adjudicate a Strickland claim addresses
only one prong, courts should extend their deferential review
under § 2254(d) to the lower court’s reasoning on the remain-
ing prong. In support of this “look through” approach, the
State points us to Wilson v. Sellers, 584 U.S. 122 (2018), which
addressed how federal courts should conduct a § 2254(d) re-
view when the last state court to adjudicate the claim issued
only a summary affirmance of a lower court’s judgment with-
out any reasoning. In such a situation, the Supreme Court in-
structs federal courts to adopt a rebuttable presumption that
the higher court agreed with the lower court’s reasoning and,
accordingly, to direct the § 2254(d) review to the reasoning of
the lower court. Id. at 128–30. Though Wilson says nothing
about applying this look through presumption when a higher

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10 No. 24-2162
court has provided reasoning for its decision, the State urges
us to extend Wilson’s logic to the review of Strickland claims.
But whatever tension—if any—exists between Wilson and
Thomas, we need not resolve this issue today. The standard of
review we apply to the performance prong is only relevant if
Nissenbaum can show that the Illinois appellate court’s deci-
sion on the prejudice prong was unreasonable under
§ 2254(d). Because Nissenbaum cannot make this showing,
we need not consider the issue of Truesdale’s performance.
B
To establish Strickland prejudice in the context of pleas, “a
defendant must show the outcome of the plea process would
have been different with competent advice.” Lafler v. Cooper,
566 U.S. 156, 163 (2012). And to show prejudice when it is al-
leged that ineffective assistance caused a plea offer to lapse,
the petitioner must demonstrate “a reasonable probability”
that (1) “they would have accepted the earlier plea offer had
they been afforded effective assistance of counsel,” (2) “the
plea would have been entered without the prosecution can-
celing it or the trial court refusing to accept it,” and (3) “the
end result of the criminal process would have been more fa-
vorable,” resulting in either a lesser charge or sentence than
the petitioner received. Missouri v. Frye, 566 U.S. 134, 147
(2012). This is a mixed question of law and fact where “rea-
sonable probability” means a probability “sufficient to under-
mine confidence in the outcome.” Strickland, 466 U.S. at 694,
698.
The Illinois appellate court concluded that Nissenbaum
could not show prejudice because even if ASA Bagby’s plea
proposal had developed into a formal offer, there was not a
reasonable probability that Nissenbaum would have accepted

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No. 24-2162 11
it—let alone that he would have done so before the offer was
withdrawn. We may only grant habeas relief if we find that
this decision was contrary to or an unreasonable application
of Supreme Court precedent. 28 U.S.C. § 2254(d)(1). This is a
demanding standard to overcome. To qualify as unreasonable
under § 2254(d), “the state court’s decision must have been
more than incorrect or erroneous,” Wiggins v. Smith, 539 U.S.
510, 520–21 (2003); rather, the error must be “beyond any pos-
sibility for fairminded disagreement.” Harrington v. Richter,
562 U.S. 86, 103 (2011).
1
Nissenbaum first argues that the Illinois appellate court
applied the wrong legal standard—more specifically, he says
that the court erroneously treated the reasonable probability
analysis as a question of pure fact and, accordingly, held him
to a heightened “manifest weight of the evidence” standard.
Under AEDPA, we do not owe deference to a state court’s de-
cision if the state has imposed “a burden contrary to law.”
Dunn v. Neal, 44 F.4th 696, 706 (7th Cir. 2022). But it is far from
clear that the Illinois appellate court in fact applied a height-
ened standard. At the outset, the appellate court correctly re-
cited and defined reasonable probability as the showing nec-
essary for Nissenbaum to establish prejudice. The court also
explained that, under Illinois law, a state appellate court re-
views the ultimate legal issue of ineffective assistance de novo
but reviews a trial court’s factual findings on a Strickland
claim deferentially under a manifest weight of the evidence
standard. People v. Stanley, 921 N.E.2d 445, 456 (Ill. App. Ct.
2009). Accordingly, the appellate court’s order references a
manifest weight standard where Nissenbaum attempted to
dispute the trial court’s factual findings.

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12 No. 24-2162
It’s true that one statement at the end of the order appears
to conflate the manifest weight standard with the question of
whether a reasonable probability existed:
Mr. Nissenbaum has failed to demonstrate a reasona-
ble probability that, but for counsel’s deficient perfor-
mance, he could or would have accepted a plea offer
from the State. He has fallen far short of demonstrating
that the trial court’s finding that this probability did
not exist was contrary to the manifest weight of the ev-
idence.
But having correctly stated and applied the legal standard
elsewhere in the order, we think it “more likely that the court
stated its conclusion imprecisely than that it applied a differ-
ent standard.” Stanley v. Bartley, 465 F.3d 810, 813 (7th Cir.
2006); see also Olvera v. Gomez, 2 F.4th 659, 670 (7th Cir. 2021)
(“When examining a state court’s articulation of the Strickland
standard, we must keep in mind the presumption that state
courts know and follow the law and give their articulation of
that standard the benefit of the doubt.”) (quotations omitted).
Though the appellate court perhaps phrased the standard
of review imprecisely in its conclusion, it is evident that the
court adequately differentiated between factual findings (to
which it applied the manifest weight standard) and the over-
arching, mixed question of reasonable probability. Cf. Dunn,
44 F.4th at 703–04 (refusing to defer under AEDPA where the
state court not only repeatedly misstated but actually applied
the improper legal standard). Here, the trial court made nu-
merous factual findings that informed the reasonable proba-
bility analysis. Most importantly, the court found that Nissen-
baum “understood he was facing a nonprobationable sen-
tence” yet “did not want an offer”—rather, it was “clear that

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No. 24-2162 13
Mr. Nissenbaum wanted a trial.” The appellate court accepted
these factual findings because Nissenbaum failed to show
they were against the weight of the evidence. Nissenbaum ar-
gues that the appellate court’s approach collapsed the reason-
able probability analysis into a question of pure fact. But the
appellate court did not simply adopt the district court’s fac-
tual findings and end the analysis there. Rather, it applied
those facts to the law and independently assessed whether
there was a reasonable probability that Nissenbaum would
have accepted an offer and could have done so before it was
revoked.
2
Having established that the state appellate court applied
the correct legal standard, we turn now to the substance of its
reasoning. As an initial matter, we agree with the appellate
court that ASA Bagby’s text message in March 2017 was not a
formal plea offer. Both Truesdale and ASA Bagby testified
that they did not understand the text message as an offer, and
the proposal was phrased only in tentative terms. A formal
plea offer is not necessarily required to show prejudice, but
Nissenbaum must “show—at a minimum—that the prosecu-
tor would have actually offered him a deal had his attorney
been competent.” Delatorre v. United States, 847 F.3d 837, 846
(7th Cir. 2017). And as the appellate court correctly observed,
the lack of a formal offer, though not dispositive, necessarily
renders Nissenbaum’s claim of prejudice more speculative.
It was likewise reasonable for the appellate court to con-
clude that even if Nissenbaum had aggressively pursued ASA
Bagby’s proposal, there was not a reasonable probability that
he could have accepted and finalized an offer before it would
have been revoked. ASA Bagby suggested a domestic battery

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14 No. 24-2162
plea on March 24, 2017, before she had an opportunity to
speak with D.K. But when ASA Bagby conferred with D.K. on
April 11, she learned that D.K. was adamantly opposed to any
plea that did not include a sex offense. ASA Bagby then im-
mediately informed Truesdale that a domestic battery plea
was off the table. And Nissenbaum’s own emails confirm that
he was “not ok with being a sex offender.” Even assuming
that ASA Bagby would not have sought D.K.’s input before
formalizing a deal, this timeline suggests that Nissenbaum
would have had only 18 days from ASA Bagby’s initial text
message to negotiate and finalize a domestic battery plea be-
fore the offer would have been withdrawn. Nissenbaum says
there was a reasonable probability that he could have final-
ized a deal on or before April 11, relying heavily on ASA
Bagby’s testimony that had Truesdale approached her want-
ing to discuss terms, she would have “negotiated a plea with
Mr. Nissenbaum on [April 11].” But this statement merely
suggests that ASA Bagby would have still been open to for-
malizing a plea prior to her meeting with D.K. It does not es-
tablish that negotiations would have proceeded quickly
enough that a plea could have been entered before ASA Bagby
met with D.K.
Even if a plea deal could have been finalized in time, Nis-
senbaum did not show there was a reasonable probability that
he would have accepted it. When evaluating prejudice, courts
cannot simply rely on “post hoc assertions from a defendant
about how he would have pleaded but for his attorney’s defi-
ciencies” and “should instead look to contemporaneous evi-
dence to substantiate a defendant’s expressed preferences.”
Lee v. United States, 582 U.S. 357, 369 (2017). Nissenbaum now
says that had he known he was facing a potential 12-year
mandatory minimum sentence, he would have jumped at the

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No. 24-2162 15
opportunity to receive a probation-only sentence. But the con-
temporaneous evidence as to his preferences undermines this
assertion.
Nissenbaum did not pursue ASA Bagby’s probation-only
proposal even though, by his own account, he believed he was
facing a potential 6-year mandatory prison sentence. Of
course, the difference between 6 and 12 years is not immate-
rial, but Nissenbaum’s reluctance to pursue a deal for proba-
tion when he knew he was facing significant prison time sug-
gests that he gave great weight to factors beyond the length of
his sentence. This conclusion is supported by other evidence
in the record. Truesdale testified that Nissenbaum was ada-
mantly opposed to having a felony record, citing this as the
reason earlier plea negotiations had fallen apart. Nissenbaum
denies this, but his own emails to Truesdale emphasized his
desire to avoid a felony conviction: “[i]f there is a chance that
anything will give me a shot at moving forward in a world
without a felony, [my parents] will support it and pay for it.”
It’s true that when Nissenbaum emailed Truesdale about a
potential plea, he said nothing about a felony—the only con-
ditions he put in writing were that he did not want prison
time and did not want to be a sex offender. But when pre-
sented with a deal that seemingly met these requirements,
Nissenbaum did nothing. From this fact, a reasonable jurist
could conclude that Truesdale’s testimony—that Nissenbaum
was unwilling to accept a plea to a felony charge—was accu-
rate and that there was therefore no reasonable probability he
would have accepted a plea to aggravated domestic battery.
Finally, Nissenbaum argues that he would have taken a
plea deal had Truesdale not given him unrealistic expecta-
tions of his chances of being acquitted at trial. But the trial

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16 No. 24-2162
court determined that Truesdale accurately advised Nissen-
baum “of the strengths and weaknesses not only of the State’s
case but of [his] own theory of his defense,” a finding Nissen-
baum has not rebutted by clear and convincing evidence. 28
U.S.C. § 2254(e)(1). Moreover, even though a “defendant
[who] has no plausible chance of an acquittal at trial” will
likely “accept a plea if the Government offers one,” Lee, 582
U.S. at 367, it’s not true that Nissenbaum faced no possibility
of acquittal. Because Nissenbaum relied on a consent defense,
the case turned largely on his and D.K.’s respective credibil-
ity. And in the lead up to trial, it was not clear whether D.K.
was going to cooperate with the prosecution or testify. Under
these circumstances, a well-informed defendant in Nissen-
baum’s position could have rationally chosen to proceed to
trial in the hope of securing an acquittal rather than take a
plea.
Because the state appellate court’s decision on the merits
of Nissenbaum’s ineffective assistance of counsel claim was
not an unreasonable application of federal law, we find that
Nissenbaum’s petition for habeas relief is barred under 28
U.S.C. § 2254(d).
A FFIRMED

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