Nathan Nissenbaum v. Chad Jennings

In the

United States Court of Appeals

For the Seventh Circuit

____________________

No. 24-2162

NATHAN NISSENBAUM,

Petitioner-Appellant,

v.

CHAD 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.

____________________

ARGUED MAY 15, 2025 — DECIDED AUGUST 5, 2025

____________________

Before RIPPLE, KIRSCH, and KOLAR, Circuit Judges.

KIRSCH, 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

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.,

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

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

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

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,

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

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.

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

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

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.

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

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

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

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

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).

AFFIRMED