James Reilly v. WILL COUNTY SHERIFF ’ S OFFICE and MICHAEL KELLEY , Will County Sheriff

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 23-3167
JAMES R EILLY ,
Plaintiff-Appellant,
v.
WILL C OUNTY S HERIFF ’ S O FFICE and MICHAEL K ELLEY , Will
County Sheriff,
Defendants-Appellees.
____________________
Appeal from the United States District Court for the
Northern District of Illinois, Eastern Division.
No. 1:23-cv-02411 — Robert W. Gettleman, Judge.
____________________
A RGUED NOVEMBER 6, 2024 — DECIDED J ULY 8, 2025
____________________
Before BRENNAN , K OLAR , and M ALDONADO, Circuit Judges.
M ALDONADO, Circuit Judge. Deputy James Reilly alleges
that his employer, the Will County Sheriff’s Office, and his
boss, Sheriff Michael Kelley, retaliated against him in viola-
tion of the First Amendment. Reilly contends that Sheriff Kel-
ley passed him over for promotion to sergeant because he crit-
icized the sheriff while running against him in the county
sheriff election. The defendants moved to dismiss Reilly’s

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2 No. 23-3167
complaint, arguing that it was untimely because Reilly filed
the complaint over two years after his eligibility for a promo-
tion expired. The district court agreed that Reilly was out of
time, granted the defendants’ motion to dismiss, and entered
judgment in their favor. Reilly requested that the district court
set aside its judgment under Federal Rule of Civil Procedure
59(e) and allow him to amend his complaint. The district court
denied leave to amend, believing that Reilly needed to pre-
sent extraordinary circumstances to justify relief and failed to
do so.
In reaching its conclusion, the district court mistakenly ap-
plied a heightened standard to Reilly’s Rule 59(e) motion, re-
quiring Reilly to present extraordinary circumstances instead
of applying the liberal standard for amending pleadings. The
court further erred in denying Reilly’s request for leave to
amend his complaint. We conclude that Reilly’s proposed
amended complaint states a plausible claim upon which relief
may be granted, and that he has not pled himself out of court
based on the statute of limitations. In doing so, we do not pre-
clude the defendants from raising the statute of limitations
defense later in the case on a more complete factual record.
We therefore vacate the judgment of the district court and re-
mand the case for further proceedings.
BACKGROUND
I. Facts
James Reilly joined the Will County Sheriff’s Office as a
deputy in 2013. With a background in law enforcement,
Reilly’s performance was very strong, and he was named
Deputy of the Year in 2016.

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No. 23-3167 3
Looking to take his career to the next level, in February of
2017, Reilly announced his campaign for Will County Sheriff
in the upcoming 2018 election. Reilly’s opponent in the elec-
tion was his boss, Sheriff Michael Kelley, who was first elected
as the county sheriff in 2014. During Reilly’s campaign, he
publicly criticized Sheriff Kelley and his performance as sher-
iff. Reilly’s campaign proved unsuccessful, and Kelley won
the 2018 election.
Before the election, in late 2017, Reilly took an exam to de-
termine his eligibility for promotion to sergeant. But passing
the exam was just one factor for Reilly’s eligibility; the promo-
tion decision was ultimately up to Sheriff Kelley. Reilly fin-
ished at the top of his class on the exam and was placed first
on the “Sergeant Promotional List,” meaning that not only
was Reilly eligible for a promotion to sergeant, but he was also
considered one of the most fit to be promoted. Reilly, how-
ever, was never selected for the promotion.
To better understand the central dispute of this case, back-
ground on the promotion process is necessary. The Merit
Commission, a five-person body which oversees the promo-
tion process, “certifies” the Sergeant Promotional List. Ac-
cording to the Commission’s rules, the sheriff can select any
deputy listed on the Sergeant Promotional List for promotion
regardless of exam scores. If, however, Sheriff Kelley selected
a candidate for promotion who ranked lower than the first
three individuals on the list, he was required to justify this
decision to the Merit Commission in writing. Conversely, if
Sheriff Kelley selected any of the first three candidates, he was
not required to provide any explanation for his decision.
Between November 11, 2018, and July 26, 2019, while
Reilly was eligible for a promotion, five other candidates were

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4 No. 23-3167
promoted to sergeant. At the time of their promotions, each of
the candidates was ranked as one of the top three on the pro-
motional list, meaning they were presumptively qualified for
the promotion and Sheriff Kelley was not required to explain
his decisions.
Reilly ran for Will County Sheriff again in the 2022 elec-
tion. During this campaign, in July of 2022, Sheriff Kelley
stated publicly that he had not promoted Reilly to sergeant
because of Reilly’s criticism during the 2018 campaign, add-
ing: “Why would I promote him? Who would do that?” Sher-
iff Kelley was reelected later that year.
II. Procedural History
On April 18, 2023, about nine months after Sheriff Kelley’s
statement about refusing to promote Reilly, Reilly filed this
lawsuit against Kelley and the Sheriff’s Office, bringing one
claim for First Amendment retaliation under 42 U.S.C. §
1983.1 Reilly alleges that Sheriff Kelley and the Sheriff’s Office
retaliated against him for criticizing Sheriff Kelley during
Reilly’s first campaign by failing to promote him to sergeant.
The defendants moved to dismiss Reilly’s complaint un-
der Federal Rule of Civil Procedure 12(b)(6). Rather than ar-
gue that Reilly’s complaint failed to state a claim, they raised
the affirmative defense that Reilly’s claim was barred by the
1 Reilly conceded below that naming both Sheriff Kelley and the Will
County Sheriff’s Office as defendants was duplicative because Reilly
brought his claim against Sheriff Kelley in his official capacity. See Ken-
tucky v. Graham, 473 U.S. 159, 165–66 (1985). Because the Will County Sher-
iff’s Office entered an appearance on appeal, we refer to it with defendant
Kelley collectively as “defendants.” On remand, the district court should
dismiss the Sheriff’s Office as a party and update the caption accordingly.

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No. 23-3167 5
two-year statute of limitations applicable to his § 1983 claim.
The defendants argued that Reilly knew of his injury no later
than November of 2019, over two years before he brought his
claim.
In opposing the motion to dismiss, Reilly argued that he
could not have known that his constitutional rights were vio-
lated until Sheriff Kelley’s public remarks on July 13, 2022.
Reilly further contended that if he had brought his case before
Sheriff Kelley made the public statements, his claim would
have been overly speculative and would not have survived
dismissal.
The district court agreed with the defendants that Reilly’s
claims were untimely and granted the motion to dismiss with
prejudice. Relying on our decision in Thelen v. Marc’s Big Boy
Corp., 64 F.3d 264 (7th Cir. 1995), the district court explained
that Reilly’s injury accrued when he was passed over for pro-
motion, which occurred at least five times between 2017 and
2019. The court thus found that Reilly’s claim accrued no later
than November of 2019, and his April 2023 complaint was
therefore brought outside the two-year statute of limitations.
The district court found no ground for equitable tolling be-
cause it concluded that a reasonable person in Reilly’s posi-
tion would have believed that he was not promoted because
of his protected activity.
In granting the defendants’ motion to dismiss, the district
court took the unusual step of simultaneously entering final
judgment in favor of the defendants, thereby precluding
Reilly from filing an amended complaint. Accordingly, Reilly
filed a motion under Rule 59(e) to alter or amend the judg-
ment and for leave to file an amended complaint under Rule
15(a)(2), with a proposed amended complaint attached. Reilly

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6 No. 23-3167
asserted that new allegations in his proposed amended com-
plaint cured any defect in his original complaint and demon-
strated that his claim was timely. Specifically, he pointed to
new allegations that the other deputies who were promoted
were presumptively qualified, that those promotions com-
plied with the Merit Commission’s rules, and that the last pro-
motion of another deputy occurred over two years after Reilly
announced his first candidacy. Reilly therefore argued that he
had no reason to suspect a constitutional injury.
The district court denied Reilly’s 59(e) motion and request
for leave to file an amended complaint. In declining to set
aside the judgment, the court found that Reilly had failed to
clearly establish that the court committed a manifest error of
law or fact, or that newly discovered evidence precluded en-
try of judgment. The court also concluded that the new alle-
gations in Reilly’s proposed amended complaint were prem-
ised on information Reilly already had but failed to present in
responding to the defendants’ motion to dismiss. Accord-
ingly, the court denied Reilly’s Rule 59(e) motion and motion
for leave to file an amended complaint.
DISCUSSION
Reilly appeals the district court’s denial of his Rule 59(e)
motion.2 We hold that the district court abused its discretion
by applying a heightened standard in denying Reilly’s Rule
2 For purposes of our review, the district court’s ruling on Reilly’s
Rule 59(e) motion merges with its prior order granting defendants’ Rule
12(b)(6) motion. See Banister v. Davis, 590 U.S. 504, 509 (2020). But because
Reilly does not raise on appeal any argument challenging the district
court’s order dismissing his original complaint, we do not independently
review that order.

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No. 23-3167 7
59(e) motion. We further conclude that Reilly’s proposed
amended complaint is legally sufficient because, at this stage,
we cannot hold as a matter of law that it is barred by the rele-
vant statute of limitations.
I. Reilly’s Rule 59(e) Motion
At the outset of our analysis, a few words are necessary to
address the unique procedural posture of this case.
In the usual course, a plaintiff whose complaint has been
dismissed at the pleading stage should be given at least one
opportunity to amend. Runnion ex rel. Runnion v. Girl Scouts of
Greater Chicago & Nw. Ind., 786 F.3d 510, 519 (7th Cir. 2015);
see also Fed. R. Civ. P. 15(a) (“The court should freely grant
leave when justice so requires.”). But when a district court en-
ters a final judgment of dismissal, amendment of the com-
plaint under Rule 15 is not available unless the judgment is
set aside or modified under Rule 59(e). Id. at 521. We review
a district court’s decision on a Rule 59(e) motion for abuse of
discretion. Cincinnati Life Ins. Co. v. Beyrer, 722 F.3d 939, 953
(7th Cir. 2013).
Relief under Rule 59(e) is generally reserved for “extraor-
dinary cases,” Runnion, 786 F.3d at 521, and for a motion to be
successful, the movant must clearly establish: “(1) that the
court committed a manifest error of law or fact, or (2) that
newly discovered evidence precluded entry of judgment.”
Cincinnati Life, 722 F.3d at 954. But when, as here, a district
court dismisses a complaint with prejudice and is confronted
with a Rule 59(e) motion to set aside the judgment, the district
court “must still apply the liberal standard for amending
pleadings under Rule 15(a)(2)” and “need not find other

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8 No. 23-3167
extraordinary circumstances” to grant the relief requested.
Runnion, 786 F.3d at 521.
In denying Reilly’s Rule 59(e) motion, the district court
failed to consider our instructions in Runnion. Because the
court entered judgment at the same time it granted the de-
fendants’ 12(b)(6) motion, it should have applied the liberal
standard for amending pleadings and did not need to find ex-
traordinary circumstances in order to grant Reilly’s requested
relief.
The district court relied on our decision in Environmental
Barrier Co., LLC v. Slurry Systems, Inc., to conclude that the
new allegations added to Reilly’s proposed amended com-
plaint were insufficient to qualify as newly discovered evi-
dence and denied relief under Rule 59(e) on this basis. 540
F.3d 598, 608 (7th Cir. 2008). But this Court reviewed the de-
nial of a Rule 59 motion in Environmental Barrier under much
different circumstances. There, we reviewed the district
court’s order denying the plaintiff’s Rule 59 motion to set
aside an arbitration award on the grounds that newly discov-
ered evidence came to light after the award was entered. Id.
The district court reviewed the newly discovered evidence
and determined that it had no effect on the propriety of the
arbitration award, and we affirmed on those grounds. Id. at
608–09. Here, by contrast, there was no “newly discovered ev-
idence” to put forward after final judgment was entered;
Reilly simply should have been given an opportunity to cure
any perceived defects in his complaint. Runnion, 786 F.3d at
523 (“[A] plaintiff who receives a Rule 12(b)(6) motion and
who has good reason to think the complaint is sufficient may
… choose to stand on the complaint and insist on a decision
without losing the benefit of the well-established liberal

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No. 23-3167 9
standard for amendment with leave of court under Rule
15(a)(2).”). Reilly only filed a Rule 59(e) motion because the
district court simultaneously entered judgment with its order
granting the motion to dismiss. We have said that “a district
court cannot nullify the liberal right to amend under Rule
15(a)(2) by entering judgment prematurely at the same time it
dismisses the complaint that would be amended.” Runnion,
786 F.3d at 522. Thus, the more liberal standard set forth in
Runnion must apply here.
The district court applied the wrong standard in deciding
Reilly’s Rule 59(e) motion and therefore abused its discretion
in denying the motion. But to determine the practical effect of
this abuse of discretion, we must answer whether Reilly’s pro-
posed amended complaint states a claim such that the lawsuit
can proceed. We find that it does.
II. Reilly’s Proposed Amended Complaint
Our analysis of whether Reilly’s amended complaint is le-
gally sufficient is guided by Federal Rule of Civil Procedure
8(c)(1), which makes clear that an affirmative defense should
be raised in a responsive pleading. Typically, affirmative de-
fenses, like timeliness, are not properly resolved at the plead-
ing stage. Vasquez v. Indiana Univ. Health, Inc., 40 F.4th 582, 588
(7th Cir. 2022).
Plaintiffs are not required to anticipate or refute potential
affirmative defenses in the complaint. Luna Vanegas v. Signet
Builders, Inc., 46 F.4th 636, 640 (7th Cir. 2022). In the “rare”
circumstance in which the complaint pleads facts that conclu-
sively establish that the plaintiff’s claim is time-barred, dis-
missal at the pleading stage can be appropriate. Id. But be-
cause timeliness issues are heavily fact-dependent, those

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10 No. 23-3167
questions are best left for summary judgment or trial so that
the court may rule on them with a complete factual record.
Sidney Hillman Health Ctr. of Rochester v. Abbott Labs., Inc., 782
F.3d 922, 928 (7th Cir. 2015). It follows that a claim will survive
dismissal “[a]s long as there is a conceivable set of facts, con-
sistent with the complaint, that would defeat a statute-of-lim-
itations defense ….” Id.
Denials of leave to amend are typically reviewed for abuse
of discretion. Runnion, 786 F.3d at 524. But when the basis for
denial is futility, as is the case here, we apply the legal suffi-
ciency standard of Rule 12(b)(6) to determine whether the
proposed amended complaint fails to state a claim. Id. (citing
Gen. Elec. Cap. Corp. v. Lease Resolution Corp., 128 F.3d 1074,
1085 (7th Cir. 1997)). Effectively, we are reviewing Reilly’s
proposed amended complaint for legal sufficiency de novo.
Id.
A complaint should only be dismissed at the pleading
stage with prejudice if the court is “certain” from the facts al-
leged that any amendment would be futile. Id. at 520. Here,
the district court found that this was one of the rare circum-
stances where Reilly had pleaded himself out of court by al-
leging facts that established that his claim was time-barred.
But in reviewing Reilly’s proposed amended complaint, we
are not certain that amendment would be futile.
The parties do not dispute that the relevant statute of lim-
itations for Reilly’s § 1983 claim is two years. Hileman v. Maze,
367 F.3d 694, 696 (7th Cir. 2004). Federal law governs the ac-
crual date for a § 1983 claim, which begins when the plaintiff
“knows or should know that his or her constitutional rights
have been violated.” Id. This is a fact-intensive inquiry “in
which both the surrounding circumstances and the claims

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No. 23-3167 11
plaintiff [himself] is trying to raise are critical.” Id. at 697
(quoting Kelly v. City of Chicago, 4 F.3d 509, 511 (7th Cir. 1993)).
For a plaintiff bringing a First Amendment retaliation
claim, the claim accrues, and the statute of limitations begins
to run, “‘immediately after the retaliatory act occurred’ … so
long as the plaintiff ‘knows or should know that his or her
constitutional rights have been violated ….’” Towne v. Don-
nelly, 44 F.4th 666, 671 (7th Cir. 2022) (quoting Gekas v. Vasili-
ades, 814 F.3d 890, 894 (7th Cir. 2016)).
The defendants contend that Reilly should have known
his constitutional rights were violated when he was passed
over for promotion no less than five times. Defendants rely on
Thelen, which the district court also relied on in dismissing
Reilly’s complaint. 64 F.3d 264 (7th Cir. 1995). We held in The-
len that the statute of limitations for the plaintiff’s ADEA
claim began to run when he was terminated, and not when he
discovered that a younger employee took over his job duties.
Id. at 267. Reasoning by analogy, the defendants argue that
Reilly should have known he was injured at the time he was
passed over for promotion and he had engaged in a protected
activity by criticizing Sheriff Kelley. In other words, the de-
fendants contend that Reilly already had sufficient infor-
mation to know that he was injured by November 2019, not
when Sheriff Kelley later publicly stated his unlawful motive.
Reilly argues that this case is more like Hileman. There, the
plaintiff, who was running for office, did not know that phony
absentee ballots voting for her opponent had been commin-
gled with valid ones, and therefore counted in the election,
even after the police had alerted her to the existence of the
phony ballots. Hileman, 367 F.3d at 695. The plaintiff brought
a § 1983 claim against the county clerk alleging constitutional

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12 No. 23-3167
violations. Id. at 696. We reversed the district court’s dismissal
of the complaint on statute of limitations grounds and con-
cluded that a reasonable plaintiff could have believed that
once the police discovered the ballots, the situation would
have been resolved. Id. at 697–98. But because of an “inexpli-
cable decision” to return the ballots to the county clerk, the
phony ballots were still counted. Id. at 698. The plaintiff there-
fore could not reasonably have known that she suffered a con-
stitutional injury until she was made aware of the commin-
gling, which occurred within the statute of limitations. Id.
Reilly argues that he similarly did not know, and could
not have known, that Sheriff Kelley’s failure to promote him
was retaliatory until Sheriff Kelley admitted so. Reilly empha-
sizes the amended complaint’s allegations that all five of the
candidates promoted to sergeant between 2017 and 2019 were
among the top three on the promotional list, meaning Sheriff
Kelley was not required to justify their promotion. Further,
“none of the promotions were close in time to Reilly’s pro-
tected speech,” and Reilly understood that one of the candi-
dates was a “personal friend” of Sheriff Kelley’s.
This case falls somewhere between Thelen and Hileman,
but closer to Hileman. The defendants’ argument that Reilly
should have suspected a potential constitutional violation
when he was not selected for promotion is viable. But so is
Reilly’s argument that he did not have sufficient information
to bring his lawsuit at the time. Perhaps Reilly is an optimistic
sort and to punish him for not jumping to the worst-case sce-
nario for his lack of promotion would be unreasonable on the
part of this Court. From the limited factual record before us,
we cannot conclude, as a matter of law, that Reilly was on suf-
ficient notice that he may have suffered a constitutional

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No. 23-3167 13
injury. Because the amended complaint pleads that Sheriff
Kelley followed the appropriate procedures, was not required
to justify his decisions, and that the promotions were not sus-
piciously close in time to Reilly’s speech, it may have been
reasonable for Reilly to believe there was nothing improper
about the decision not to promote him.
For these reasons, the allegations in Reilly’s proposed
amended complaint at the very least state a plausible claim
that a reasonable person would not have known of a potential
constitutional injury until Sheriff Kelley admitted to his retal-
iatory motive. See Clark v. City of Braidwood, 318 F.3d 764, 768
(7th Cir. 2003) (holding that if the plaintiff could prove that a
reasonable person would not have discovered the injury ear-
lier, he would have a defense to the timeliness defense raised
by the defendant). Accordingly, Reilly’s proposed amended
complaint states a claim, and dismissal on statute of limita-
tions grounds was premature.
To be sure, defendants are not precluded from raising
timeliness as a defense in the future on a complete factual rec-
ord. Reilly, similarly, is not precluded from raising other re-
sponses to the statute of limitations defense, such as the doc-
trine of equitable tolling.
CONCLUSION
The district court applied the wrong standard in review-
ing Reilly’s Rule 59(e) motion to set aside its judgment dis-
missing Reilly’s complaint. Reilly’s proposed amended com-
plaint states a claim, and, on the limited facts before us, we
cannot with certainty hold that his claim is time-barred. The
final judgment of the district court is therefore VACATED,

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14 No. 23-3167
and the case is REMANDED for further proceedings con-
sistent with this opinion.

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