Salvatore Ziccarelli v. Thomas J. Dart

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 24-2377
S ALVATORE Z ICCARELLI ,
Plaintiff-Appellant,
v.
THOMAS J. DART, et al.,
Defendants-Appellees.
____________________
Appeal from the United States District Court for the
Northern District of Illinois, Eastern Division.
No. 1:17-cv-03179 — John J. Tharp, Jr., Judge.
____________________
A RGUED A PRIL 10, 2025 — DECIDED J UNE 30, 2025
____________________
Before R IPPLE, HAMILTON , and S CUDDER , Circuit Judges.
HAMILTON , Circuit Judge. This case arises under the Family
and Medical Leave Act of 1993 (FMLA or Act), 29 U.S.C.
§ 2601 et seq. Plaintiff Salvatore Ziccarelli is a former em-
ployee of defendant Cook County Sheriff’s Office. In 2016,
Ziccarelli called Wylola Shinnawi, FMLA coordinator for the
Sheriff’s Office. During that call, we must assume on appeal,
Shinnawi warned him to “not use any more time or you will

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2 No. 24-2377
be disciplined.” Ziccarelli used one more day of FMLA leave
and then resigned.
Ziccarelli then filed this suit alleging violations of federal
law. After the district court granted summary judgment for
the Sheriff’s Office, we affirmed on most issues but reversed
and remanded for trial on Ziccarelli’s FMLA interference
claim. Ziccarelli v. Dart (“Ziccarelli I”), 35 F.4th 1079, 1092 (7th
Cir. 2022). Before trial on the FMLA interference claim, the
parties and the court discussed whether Ziccarelli could re-
ceive damages such as lost wages that resulted from his res-
ignation. That conversation focused on whether Ziccarelli
could seek damages under a theory of constructive dis-
charge—the idea that he was forced to resign—a theory that
we rejected when discussing Ziccarelli’s retaliation claim in
Ziccarelli I. Id. at 1090–92 (expressing skepticism of construc-
tive discharge damages stemming from Ziccarelli’s interfer-
ence claim as well).
At trial upon the close of Ziccarelli’s case, counsel for the
Sheriff’s Office orally moved for “a judgment of directed find-
ing.” She then asked if she should do that “in front of the jury
or at sidebar,” but said nothing more. The court took the mo-
tion under advisement, and the jury later returned a verdict
of $240,000 for Ziccarelli. The Sheriff’s Office then renewed its
motion for judgment as a matter of law under Federal Rule of
Civil Procedure 50(b), arguing that Ziccarelli could not show
prejudice resulting from any alleged interference because he
took an additional day of FMLA leave after the disputed
phone call. The district court granted that motion and, in the
alternative, conditionally granted a new trial.
Ziccarelli has appealed. He argues that the district court
erred in granting the Sheriff’s Office’s Rule 50(b) motion

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No. 24-2377 3
because the “law and facts that entitle the movant to the judg-
ment” were not specified in the pre-verdict motion as re-
quired by Rule 50(a). He also contends there is sufficient evi-
dence in the record to show he was prejudiced by Shinnawi’s
interference. We agree with Ziccarelli that the grounds under-
lying the Rule 50(b) motion were not properly presented be-
fore the verdict, so we reverse the district court’s entry of
judgment as a matter of law. However, we affirm the district
court’s alternative decision granting a new trial.
I. Background
Salvatore Ziccarelli began working as a correctional officer
for the Cook County Sheriff’s Office in 1989. In 2011, Ziccarelli
started using intermittent FMLA leave to manage his post-
traumatic stress disorder (PTSD). The Sheriff’s Office ap-
proved his taking up to seven days of FMLA leave per month
and allowed him to use accumulated sick leave to receive his
regular salary while on FMLA leave.
In 2016, Ziccarelli’s PTSD worsened. His doctor recom-
mended that he take eight weeks off for treatment. Sometime
during the week of September 12, Ziccarelli contacted Shin-
nawi, the Sheriff’s FMLA coordinator, apparently to discuss
taking his FMLA leave in large chunks (called “block leave”).
The substance of that telephone call is hotly disputed. Given
the jury’s verdict, we must credit Ziccarelli’s version, which is
that Shinnawi warned him to “not use any more [FMLA
leave] or you will be disciplined.” See, e.g., Futrell v. J.I. Case,
38 F.3d 342, 346 (7th Cir. 1994) (when district court grants
judgment as a matter of law, we view evidence and reasona-
ble inferences in light most favorable to “party winning the
verdict”). Ziccarelli used one more day of FMLA leave the

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4 No. 24-2377
following Monday, September 19. On September 20, he re-
signed.
Ziccarelli then filed this lawsuit alleging (as relevant to
this appeal) that the Sheriff’s Office interfered with his FMLA
rights and retaliated against him in violation of the statute.
After the district court granted summary judgment for the
Sheriff’s Office on both claims, we affirmed summary judg-
ment on the retaliation claim. See Ziccarelli I, 35 F.4th at 1092.
Ziccarelli’s theory of retaliation was that the Sheriff’s Office
had constructively discharged him after he inquired about
taking block leave. Id. at 1084. We found this theory untena-
ble: “A reasonable person [in Ziccarelli’s position] likely
would have thought he had several options short of immedi-
ate retirement under these facts, especially when Ziccarelli
had not yet even applied for FMLA leave and any potential
discipline remained remote.” Id. at 1091.
We nonetheless reversed summary judgment on
Ziccarelli’s interference claim, taking the opportunity to
straighten out some “varying language that ha[d] led to some
confusion” in our FMLA interference case law. Id. at 1084. We
clarified that a plaintiff like Ziccarelli could show interference
with his FMLA rights—and “prejudice” resulting from that
interference—without showing “actual denial” of leave time.
Id. at 1089. But we added a caution related to the issue of con-
structive discharge:
One feature of this case makes the prejudice
analysis for plaintiff’s interference claim more
complicated: his decision to retire from the
Sheriff’s Office shortly after his conversation
with Shinnawi. As we explain below, even
plaintiff’s version of that conversation falls far

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No. 24-2377 5
short of evidence that could support a claim for
constructive discharge. Plaintiff knew that he
had some remaining FMLA leave, sick leave,
and annual leave available for 2016. He also
knew that Shinnawi was the FMLA specialist,
and she had said nothing to address his use of
sick leave that he says he wanted to use up,
along with FMLA leave, to take the eight weeks
of leave for the treatment program his doctor
recommended. We do not see how an employee
in plaintiff’s situation could reasonably just give
up and walk away from his job, benefits, and
treatment plan entirely based on one conversa-
tion in which, under his version of the facts, the
employer’s representative was simply wrong.
The district court may have its hands full on re-
mand, particularly if plaintiff tries to blame
snowballing consequences, including even
early retirement, on his conversation with Shin-
nawi. As skeptical as we might be about those
efforts, we believe those issues need to be sorted
out in the district court in the first instance.
Id. at 1090.
After we remanded the case for trial on the FMLA inter-
ference claim, potential damages were disputed. The Sheriff’s
Office filed a motion in limine asking the court to exclude ev-
idence suggesting that Ziccarelli might be entitled to backpay,
pension credit, or reinstatement, just the sort of “snowball-
ing” consequences we had in mind. Ziccarelli opposed that
motion, arguing that he could show prejudice—an element of
his FMLA interference claim—by showing that he would

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6 No. 24-2377
have structured his leave differently if he had not suffered in-
terference and that resulting damages should be a question
for the jury.
The district court held two pre-trial conferences on this
and related issues. It first clarified its view that FMLA inter-
ference should be assessed from the perspective of a reasona-
ble employee. The court then noted our holding in Ziccarelli I
that a reasonable person in Ziccarelli’s position would not
have resigned, prompting Ziccarelli’s lawyer to ask “what’s
the issue that we’re trying? What’s left?” The district court re-
sponded that a reasonable person in Ziccarelli’s position
might have nonetheless suffered some harm from the inter-
ference: “What’s left is a reasonable person … might have
given up the idea that I’m going to get any more FMLA leave
and … maybe he would have structured his leave differently.
Maybe he would have invoked sick pay or vacation pay or in
some other way responded and … those reactions may not
have been irrational….” Dkt. 851 at 14. Later in that confer-
ence, the court and both parties acknowledged that Ziccarelli
might be able to seek unpaid sick pay. But the court again
asked whether Ziccarelli could seek resignation-related dam-
ages in light of our Ziccarelli I holding that a reasonable em-
ployee would not have resigned. The judge postponed further
discussion about the damages Ziccarelli could seek.
Roughly a week later, the court held a second pre-trial
conference focused on jury instructions. It noted that the
FMLA’s text allows recovery of “direct” damages, see 29
U.S.C. § 2617(a)(1)(A)(i)(II), but reiterated its skepticism—
based on our discussion in Ziccarelli I—that Ziccarelli could
seek damages under a theory of constructive discharge or
damages from related “snowballing consequences.” The

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No. 24-2377 7
court nonetheless read Ziccarelli I to imply that some damages
could be available “beyond recovery of accrued sick leave
benefits,” and accordingly decided to instruct the jury
broadly: Ziccarelli could receive as damages “any loss of
wages and benefits that was directly caused by the … Sheriff’s
Office’s interference with his ability to take FMLA leave.” De-
spite deciding to give this broad instruction, the court cau-
tioned that it might later consider a Rule 50 motion or remit-
titur motion with respect to damages.
The case was tried to a jury. At the close of Ziccarelli’s case,
counsel for the Sheriff’s Office made an oral motion for “a
judgment of directed finding.” Dkt. 865 at 277. She asked
whether she should do that “in front of the jury or at sidebar?”
The court responded: “It’s of record now. I’ll take it under ad-
visement.” Id. The jury ultimately returned a verdict for
Ziccarelli, awarding him $240,000.
The Sheriff’s Office then filed a Rule 50(b) renewed motion
for judgment as a matter of law, a Rule 59 motion for a new
trial, and a motion for remittitur. Ziccarelli objected that the
oral pre-verdict Rule 50(a) motion did not adequately, in the
language of the rule, “specify the judgment sought and the
law and facts that entitle the movant to the judgment.” The
court concluded that Ziccarelli had notice of the grounds for
the Rule 50(b) motion, citing its pretrial skepticism that
“Ziccarelli’s damages could include … the loss of his job” and
its warning that it might later entertain a Rule 50 motion.
Ziccarelli v. Dart (“JMOL Order”), No. 17-cv-3179, 2024 WL
3740602, at *5 (N.D. Ill. Aug. 7, 2024). On the merits, the court
held that trial evidence highlighted that Ziccarelli “took
FMLA leave after his phone call with Ms. Shinnawi,” which
negated “any reasonable inference that Ms. Shinnawi’s

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8 No. 24-2377
statements in her phone call with Mr. Ziccarelli caused him
not to take FMLA leave.” Id. at 6. The court granted judgment
as a matter of law for the Sheriff’s Office and a conditional
new trial if the judgment were later vacated or reversed.
II. Analysis
On appeal, Ziccarelli challenges the district court’s ruling
on the proper Rule 50 procedure, the substance of the judg-
ment as a matter of law, and the new trial ruling. We begin by
addressing the Rule 50 issues, then consider the new trial or-
der.
A. Rule 50 Grounds
Federal Rule of Civil Procedure 50(a)(2) provides that a
court can grant a motion for judgment as a matter of law made
“any time before the case is submitted to the jury.” Rule
50(a)(2) also requires the motion to “specify the judgment
sought and the law and facts that entitle the movant to the
judgment.” If a court does not grant a motion for judgment as
a matter of law made under Rule 50(a), the court may enter-
tain a “renewed” post-verdict motion under Rule 50(b). “Be-
cause the Rule 50(b) motion is only a renewal of the preverdict
motion, it can be granted only on grounds advanced in the
preverdict motion.” Thompson v. Memorial Hospital of Carbon-
dale, 625 F.3d 394, 407 (7th Cir. 2010) (finding argument first
raised in Rule 50(b) motion was not preserved), quoting Wal-
lace v. McGlothan, 606 F.3d 410, 418 (7th Cir. 2010); accord,
Exxon Shipping Co. v. Baker, 554 U.S. 471, 485 n.5 (2008) (“A
motion under Rule 50(b) is not allowed unless the movant
sought relief on similar grounds under Rule 50(a) before the
case was submitted to the jury.”). Here, the district court con-
cluded that the grounds for the Sheriff’s Office’s Rule 50(b)

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No. 24-2377 9
motion were preserved because the parties and the court dis-
cussed evidence of prejudice before trial. JMOL Order, 2024
WL 3740602, at *5. We do not see the pre-trial conferences the
same way, so we must reverse the grant of judgment as a mat-
ter of law.
1. Standard of Review
An unbriefed threshold question is the standard of review
we should apply to a district court’s decision that grounds
were properly preserved in a Rule 50(a) motion. While we re-
view de novo the substance of a decision granting judgment
as a matter of law, Beverly v. Abbott Laboratories, 107 F.4th 737,
748 (7th Cir. 2024), we have not explained how we review an
underlying decision on whether grounds were properly pre-
served. Other authorities also reflect that the standard of re-
view is unclear. See 9B Wright & Miller, Federal Practice and
Procedure § 2537 (3d ed. 2025) (“The standard of review for
determining preservation of issues is unclear.”); Cornwell En-
tertainment, Inc. v. Anchin, Block & Anchin, LLP, 830 F.3d 18,
25–26 (1st Cir. 2016) (noting ambiguity).
We conclude that the appropriate standard of review is for
abuse of discretion. The Eighth Circuit seems to be the only
circuit to have addressed the issue expressly, and it reviews
for abuse of discretion. Olsen as Trustee for Xurex, Inc. v. Di
Mase, 24 F.4th 1197, 1202 (8th Cir. 2022) (“This court reviews
for abuse of discretion the district court’s determination about
what grounds were raised by a 50(a) motion.”). Language in
our precedents supports this framework. See, e.g., Andy Mohr
Truck Center, Inc. v. Volvo Trucks North America, 869 F.3d 598,
605 (7th Cir. 2017) (approving decision to reach merits of Rule
50(b) motion when district court “reasonably found that [de-
fendant] was not trying to slip a new point into the case”).

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10 No. 24-2377
Plus, an abuse of discretion standard makes the most sense.
As we explain below, whether a Rule 50(a) motion adequately
specified the grounds for judgment will depend on trial con-
text, making it a fact-bound inquiry best resolved by the dis-
trict court in the first instance. We will show deference to that
decision, though we do not delegate it entirely to the district
court. See also, e.g., Dolin v. GlaxoSmithKline LLC, 951 F.3d 882,
888 (7th Cir. 2020) (motion for relief from judgment reviewed
for abuse of discretion because judges must “‘weigh incom-
mensurables’” (quoting Metlyn Realty Corp. v. Esmark, Inc., 763
F.2d 826, 831 (7th Cir. 1985)); People of State of Ill. ex rel. Harti-
gan v. Peters, 871 F.2d 1336, 1340 (7th Cir. 1989) (whether party
received adequate notice before injunction was issued is com-
mitted “primarily to the district court’s discretion”).
2. Notice of Rule 50(b) Grounds
The district court granted the Sheriff’s Office’s Rule 50(b)
motion because evidence at trial showed that Ziccarelli “took
FMLA leave after his phone call with Ms. Shinnawi.” JMOL
Order, 2024 WL 3740602, at *6. It found that this fact negated
“any reasonable inference” of prejudice. Id. Even under an
abuse of discretion standard, we conclude that the Sheriff’s
Office’s Rule 50(a) motion did not provide Ziccarelli with no-
tice of this ground for judgment as a matter of law.
Some background on Rule 50 clarifies why the Sheriff’s Of-
fice’s Rule 50(b) motion should have been denied here. Rule
50(a) motions must be made with specificity because “the pur-
pose of the rule is to allow the responding party an oppor-
tunity to cure any defect in its case before it is submitted to
the jury.” Laborers’ Pension Fund v. A & C Environmental, Inc.,
301 F.3d 768, 777 (7th Cir. 2002), citing Rule 50, Advisory
Committee Notes, 1991 Amendment; see also Urso v. United

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No. 24-2377 11
States, 72 F.3d 59, 61 (7th Cir. 1995) (“Rule 50 is designed to
flush out reasons so that errors may be prevented without the
need for appellate intervention.”); Parts & Electric Motors, Inc.
v. Sterling Electric, Inc., 826 F.2d 712, 716 (7th Cir. 1987) (col-
lecting cases). In other words, we enforce the Rule 50 specific-
ity requirement to prevent a litigant from waiting until the
end of the trial to cry “gotcha!” Sunny Handicraft (H.K.) Ltd. v.
Envision This! LLC, 66 F.4th 1094, 1098 (7th Cir. 2023). We try
to apply Rule 50 with reference to this concern. Cf. Laborers’
Pension Fund, 301 F.3d at 777 (“We have been insistent on strict
compliance with the rule when the reason for the rule is
served. We have not demonstrated that same insistence when
the rationale of the rule is not well served by such an applica-
tion.”), citing Szmaj v. American Telephone & Telegraph Co., 291
F.3d 955, 957–58 (7th Cir. 2002) (excusing failure to make Rule
50 argument at close of evidence in situation where eviden-
tiary defect “rationale collapses”).1
Because Rule 50(a)’s specificity requirement serves a no-
tice function, the question is whether the non-moving party
should have understood the grounds that were raised by the
1 The parties dispute whether Dupree v. Younger governs the Rule 50
issue. 598 U.S. 729 (2023). Dupree is not instructive here because it ad-
dressed an entirely different issue: whether a post-trial Rule 50 motion is
required to preserve a purely legal issue for appellate review when that
issue was raised earlier in the case, such as in summary judgment practice.
See id. at 734 (sufficiency-of-evidence challenges must be made after trial
to preserve issue because pre-trial factual disputes become “ancient his-
tory” after trial, quoting Empress Casino Joliet Corp. v. Balmoral Racing Club,
Inc., 831 F.3d 815, 824 (7th Cir. 2016)); id. at 735–36 (legal issues, which are
not superseded by later developments in the litigation, do not need to be
rehashed after trial to be preserved). Dupree did not address the relation-
ship between pre- and post-trial Rule 50 motions.

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12 No. 24-2377
Rule 50(a) motion. Such an assessment should encompass the
broader trial context, including arguments made outside the
four corners of a Rule 50(a) motion. The trial judge “has the
feel of the case which no appellate printed transcript can im-
part.” Unitherm Food Systems, Inc. v. Swift-Eckrich, Inc., 546 U.S.
394, 401 (2006), quoting Cone v. West Virginia Pulp & Paper Co.,
330 U.S. 212, 216 (1947). That case-based expertise may lead a
district court to find that a Rule 50(a) motion adequately spec-
ified the “law and facts that entitle the movant to the judg-
ment” even when the motion itself did not explicitly discuss
every factual or legal detail.
We acknowledged that point in Laborers’ Pension Fund,
where we held that a Rule 50(a) motion properly preserved
grounds for a Rule 50(b) motion when the supporting argu-
ments had been made “over and over again” and the non-
moving party “was made well aware of the grounds” for the
Rule 50(a) motion by various pre-trial motions. 301 F.3d at
777. As a result, “the function of Rule 50 ha[d] been served
and the issue preserved for appeal.” Id., quoting Urso, 72 F.3d
at 61; see also Parts & Electric Motors, 826 F.2d at 716–17 (re-
viewing several trial filings to determine whether Rule 50(b)
ground was preserved); Moran v. Raymond Corp., 484 F.2d
1008, 1010 n.1 (7th Cir. 1973) (finding grounds preserved for
appeal when prior argument made issue “abundantly
clear”).2
2 Laborers’ Pension Fund relied on an older version of Rule 50, which
was amended in 2006 to permit renewal of any Rule 50(a) motion—delet-
ing the requirement that the motion have been made at the close of all
evidence. See Production Specialties Group, Inc. v. Minsor Systems, Inc., 513
F.3d 695, 699 n.1 (7th Cir. 2008), quoting Rule 50, Advisory Committee
Notes, 2006 Amendment. The amendment did not change Rule 50’s

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No. 24-2377 13
The district court concluded here that Ziccarelli knew of
the “extra day” ground for the Sheriff’s Office’s Rule 50(a)
motion because of discussion in a pretrial conference. JMOL
Order, 2024 WL 3740602, at *5. For two reasons, we conclude
that pretrial proceedings did not make this ground ade-
quately clear. First, nothing in the pretrial transcripts or fil-
ings mentioned the specific fact upon which the district court
granted judgment as a matter of law: that Ziccarelli took an
extra day of FMLA leave on September 19. The district court
seemed to recognize this, explaining that this evidence
“emerged at trial.” Id. at *6. If a significant piece of evidence
does not “emerge” until trial, it will be difficult for a pre-trial
conference to have notified the non-moving party of the sig-
nificance of that evidence for Rule 50 purposes. This is espe-
cially true here. There was little testimony discussing
Ziccarelli’s one day of leave on September 19, and Ziccarelli
contends correctly that the issue was not highlighted until
closing arguments (and even then, it was discussed only
briefly). Dkt. 865 at 314 (closing argument); id. at 256 (only
testimony discussing extra day of leave, Ziccarelli stating:
“Well, I still had FMLA, so I used a little bit before I got fired,
or thought I’d get fired.”).
The second problem is that the pretrial filings and tran-
scripts focused on whether Ziccarelli could seek damages
“snowballing” from his resignation, not whether Ziccarelli
could show prejudice at all and therefore prove liability not-
withstanding his having taken FMLA leave on September 19.
This mismatch is important because of the notice concerns un-
derlying Rule 50. A party may rely on specific facts or
specificity requirement and does not change Laborers’ Pension Fund’s rele-
vance here.

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14 No. 24-2377
arguments not expressed in a Rule 50(a) motion only when
the non-moving party is clearly on notice of a more general
argument in the same genre. See, e.g., Andy Mohr Truck Center,
869 F.3d at 605 (affirming decision to consider Rule 50(b) mo-
tion when Rule 50(a) motion focused on lack of evidence to
show unfair discrimination and Rule 50(b) motion attacked
evidence as cherry-picked because “these all add up to the
same thing”). That’s not what we have here because the pre-
trial arguments focused on the availability of a specific cate-
gory of damages.
The district court concluded that pretrial discussion of res-
ignation-related damages also put Ziccarelli on notice of a po-
tential prejudice problem: “Prejudice means harm, and dam-
ages are the quantification of that harm.” JMOL Order, 2024
WL 3740602, at *5. We agree that damages are generally a
“quantification” of prejudice—and that damages and liability
can be closely related in cases like this one where prejudice is
an element of the plaintiff’s case. But that does not solve the
problem here because the pre-trial discussions (as relevant to
this appeal) focused specifically on whether Ziccarelli could
seek damages flowing from his resignation. That says nothing
about whether he could seek other damages or show preju-
dice in other ways.
A recent FMLA decision helps clarify the point. In Simon
v. Cooperative Educational Service Agency #5, the plaintiff al-
leged FMLA interference after the defendant, a school, failed
to return her to an equivalent position following her FMLA
leave. 46 F.4th 602, 604–05 (7th Cir. 2022). By trial, the plaintiff
sought only injunctive and declaratory relief—specifically, “a
declaration that [the school] had violated the FMLA when it
failed to return Simon to an equivalent position following her

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No. 24-2377 15
leave.” Id. at 605. The district court granted declaratory relief
and the school appealed, arguing that the FMLA did not sup-
port declaratory relief and the plaintiff had not suffered prej-
udice. We rejected both arguments. First, we explained that
the FMLA authorizes “equitable relief,” which includes de-
claratory judgments. Id. at 611; see also 29 U.S.C. § 2617(a)(2).
Second, we explained that the plaintiff had proved prejudice
by being forced to work “below her professional capacity” for
a year even though she had not sought financial damages. Id.
at 612. The fact that she had been placed in a less desirable
position, alone, was “harm for which the FMLA provides a
remedy.” Id. Simon shows that the question of money dam-
ages—the issue discussed pre-trial in this case—is distinct
from whether there has been an FMLA violation in the first
place.
Both the district court and the defendants, in rejecting
Ziccarelli’s theory of damages, acknowledged that Ziccarelli
might be able to show prejudice short of constructive dis-
charge. In the first pre-trial conference, the court explained
that Ziccarelli might be able to show a consequence from the
interference “that didn’t reach the point of constructive dis-
charge.” Dkt. 851 at 12. It noted that “a reasonable person
might have given up the idea that I’m going to get any more
FMLA leave and … maybe he would have structured his leave
differently. Maybe he would have invoked sick pay or vaca-
tion pay or in some other way responded….” Id. at 14. This is
true—Ziccarelli might have been able to make this showing—
and it highlights the question Ziccarelli might have addressed
through further testimony if the prejudice argument had been
properly presented in a Rule 50(a) motion. Indeed, the Sher-
iff’s Office explains that in the pretrial conference it argued
Ziccarelli should not be able to seek “wages he would have

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16 No. 24-2377
earned had he not retired”—not that he could not show prej-
udice at all. Before trial, the district court and defendants both
seemed to believe that Ziccarelli could, for example, seek pay-
ment of his accrued sick leave even if he could not seek dam-
ages resulting from his resignation. See Dkt. 863 at 35–36 (say-
ing Ziccarelli I implied that Ziccarelli could receive something
“beyond recovery of accrued sick leave benefits”); see also
Dkt. 851 at 37 (defense counsel saying that “the only damages
that … Ziccarelli would be entitled to is the 176 hours of sick
leave”).
To be thorough, we also reviewed the motions in limine to
see if any of them should have put Ziccarelli on notice that the
district court might grant judgment as a matter of law based
on Ziccarelli’s additional day of leave when the Sheriff’s Of-
fice made its content-free Rule 50(a) motion during trial. The
Sheriff’s Office’s motion asked the court to exclude evidence
on backpay, pension credit, and reinstatement, but acknowl-
edged that those potential damages were separate from
Ziccarelli’s “remaining sick leave.” Dkt. 840 at 3-4. It re-
quested that, “other than his remaining sick leave that he
could have used in conjunction with his remaining FMLA
time and which he was not paid out for when he retired, this
Court should preclude this damages testimony and asking for
such an award because these damages are not permitted un-
der the circumstances.” Id. at 4 (footnote omitted). This mo-
tion confirms that the pretrial conversations were aimed at
only post-resignation damages, not the consequences of
Ziccarelli’s one more day of FMLA leave.
The only potential indication that the district court’s pre-
trial concern might go to liability is that the court invoked
Rule 50. But that comment suggested the possibility of a “Rule

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No. 24-2377 17
50 motion with respect to damages” if the court felt that “the
damage award is unjustified.” JMOL Order, 2024 WL 3740602,
at *5 (emphases added). Even the district court’s invocation of
Rule 50 focused on a different issue than the one on which it
ultimately granted judgment as a matter of law. And else-
where in the same discussion, the court hinted that another
possible procedural vehicle might be a motion for remittitur,
further highlighting that the concern was not a substantive el-
ement of Ziccarelli’s case: “whatever the procedural format …
those are options available to the Court if I think that the fac-
tual record that is developed at trial simply does not support
as a matter of law damages arising from Mr. Ziccarelli’s
choice to terminate his employment with the Sheriff’s Office.”
Dkt. 863 at 39–40.
These pretrial discussions did not notify Ziccarelli of an
argument that he might not be able to show prejudice because
he took that one additional day of FMLA leave, which was the
specific ground on which the district court granted judgment
as a matter of law. That makes the judgment procedurally im-
proper. See, e.g., Production Specialties Group, 513 F.3d at 699
(affirming denial of Rule 50(b) motion when argument was
not made pre-verdict); Wallace v. Flintco, 143 F.3d 955, 963 (5th
Cir. 1998) (finding non-compliance with Rule 50(a) when
moving party did not “alert” non-moving party to grounds
for sufficiency of evidence challenge and “allow” non-moving
party the “opportunity to move to cure any such deficiency”).
The Sheriff’s Office makes three additional arguments on
this procedural issue. First, it focuses on Ziccarelli’s counsel’s
pretrial statement that “it was crazy for him to quit. … It was
not objectively reasonable for him to quit based on what Ms.
Shinnawi said.” According to the Sheriff’s Office, this

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18 No. 24-2377
amounted to a binding admission that Ziccarelli could not
show prejudice. We do not see it that way. The statement
highlights the limited scope of damages available to Ziccarelli
in this action, but it says nothing about whether he could
show prejudice notwithstanding the one day of post-interfer-
ence FMLA leave.
The Sheriff’s Office next points out that it asked the district
court how to properly preserve its Rule 50(a) motion and that
the district court responded that the motion was “under ad-
visement.” The Sheriff’s Office essentially argues that we
should not penalize it for not pressing the contents of its ar-
gument on a district court that seemed at least reluctant to
spend time listening to them and/or thought they were not
needed.
We see the point, but on these facts, we disagree with the
conclusion. There are plenty of circumstances in which law-
yers must comply with procedural requirements to preserve
arguments for later in the trial or appellate review, even when
a district judge may express impatience or resistance to hear-
ing the argument. See, e.g., Levin v. Joseph E. Seagram & Sons,
158 F.2d 55, 58 (7th Cir. 1946) (litigant must object to jury in-
structions; “before he can claim prejudice thereby he will have
to do more than acquiesce in the court’s response which he
thinks unsatisfactory”); see also Divane v. Krull Electric Co., 194
F.3d 845, 849 (7th Cir. 1999) (“While a party may believe it
would be futile … and that the objection may irritate the
court, it is still incumbent upon the party to make the objec-
tion in order to preserve the issue for appeal.” (alterations
omitted, quoting Johnson v. Ashby, 808 F.2d 676, 679 (8th Cir.
1987))); Moran, 484 F.2d at 1011 (“it is incumbent on counsel
to make the record in the district court as to issues he wishes

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No. 24-2377 19
to present on appeal”). Rule 50 presents one of those situa-
tions. The judge did not express any such impatience or reluc-
tance here. But even if a district judge makes clear that she or
he does not want to hear the grounds for a Rule 50(a) motion
(which a judge should not do), counsel must still make those
grounds clear, whether orally or in writing or both. See, e.g.,
Passananti v. Cook County, 689 F.3d 655, 660 (7th Cir. 2012) (oral
motion accompanied by written document).
Finally, the Sheriff’s Office offers its own procedural ri-
poste. It argues that because Ziccarelli did not challenge the
specificity of its Rule 50(a) motion when it was made, he has
waived such a challenge now. We disagree. In Wallace v.
McGlothan, the Sheriff’s Office’s primary authority for this ar-
gument, the non-moving party did not object to an argument
raised for the first time in a Rule 50(b) motion and instead re-
sponded on the merits. 606 F.3d 410, 419 (7th Cir. 2010). We
explained that, to preserve the procedural challenge for ap-
peal, “the plaintiff must have objected when the defendant
made his post-verdict motion.” Id. Wallace does not stand for
the premise that a non-moving party must object to an insuf-
ficiently specific pre-verdict motion, but that a litigant must
object to an insufficiently specific post-verdict motion to pre-
serve its procedural argument for appeal.
Here, Ziccarelli promptly and vigorously objected that the
Sheriff’s Office did not present any of its Rule 50(b) arguments
in its pre-verdict motion. Ziccarelli made those procedural ar-
guments both orally, after the Sheriff’s Office orally renewed
its pretrial motion, see Dkt. 865 at 335, and in writing. Dkt.
871. That puts this case outside the scope of Wallace.
Unlike in the cases cited by the Sheriff’s Office, arguments
on the specific relevance of Ziccarelli’s one extra day of FMLA

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20 No. 24-2377
leave were not “forcefully presented to the district court,” so
the function of Rule 50 was not served. See Urso, 72 F.3d at 61.
Accordingly, we reverse the district court’s entry of judgment
as a matter of law without addressing the merits.
B. New Trial
The district court conditionally granted a new trial under
Rule 59 in the alternative to its judgment as a matter of law
ruling. Rule 50 and Rule 59 motions are subject to different
standards, and a new trial may be proper even when a litigant
fails to preserve adequately grounds for judgment as a matter
of law. E.g., Abellan v. Lavelo Property Mgmt., LLC, 948 F.3d
820, 831 (7th Cir. 2020) (“Lavelo did not properly preserve
these issues as grounds for judgment as a matter of law, but it
did present them properly as grounds for a new trial.”); see
also Mejia v. Cook County, 650 F.3d 631, 634 (7th Cir. 2011) (ex-
plaining difference between Rule 50 and Rule 59 standards).
A new trial presents an opportunity to remedy an evidentiary
defect—which is denied when there is a “gotcha” Rule 50 mo-
tion. See Morrison Knudsen Corp. v. Fireman’s Fund Insurance
Co., 175 F.3d 1221, 1260 (10th Cir. 1999) (collecting cases:
“Courts of appeals have often ordered new trials rather than
JMOL when a plaintiff could likely remedy its deficient evi-
dence in a new trial.”).3
3 Ziccarelli asserts that the new trial motion was improper because the
Sheriff’s Office did not move for a new trial prior to the verdict. Rule 59(b)
provides that a motion for a new trial must be filed “no later than 28 days
after the entry of judgment.” It has no other preservation or timeliness re-
quirements relevant to this appeal, and unlike Rule 50, does not require a
pre-verdict motion that must be renewed. See Umpleby v. Potter & Brum-
field, Inc., 69 F.3d 209, 212–13 (7th Cir. 1995) (party does not need to move
for a new trial before verdict). Ziccarelli cited Jackson v. Esser, 105 F.4th 948,

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No. 24-2377 21
A district court’s discretion in considering a motion for a
new trial is “wide and our review deferential.” Mejia, 650 F.3d
at 634. The district court may assess the evidence presented
and grant a new trial when it believes that the verdict went
against the “manifest weight” of the evidence. Id. However,
“a legal error can amount to an abuse of discretion.” Ruiz-Cor-
tez v. City of Chicago, 931 F.3d 592, 602 (7th Cir. 2019).
Here, the district court granted a new trial for the same
substantive reason it granted judgment as a matter of law. It
concluded that Ziccarelli had presented “insufficient evi-
dence of prejudice.” The court wrote that, notwithstanding
the threats attributed to Ms. Shinnawi, Mr.
Ziccarelli took FMLA leave after his phone call
with Ms. Shinnawi, and he was not disciplined
for taking that leave (or any prior leave). This
fact negates any reasonable inference that Ms.
Shinnawi’s statements in her phone call with
Mr. Ziccarelli caused him not to take FMLA
leave. Accordingly, the trial evidence is insuffi-
cient to support a jury finding of prejudice….
JMOL Order, 2024 WL 3740602, at *6 (footnote omitted).
We affirm the conditional grant of a new trial. The district
court’s new trial ruling was not an abuse of discretion for two
reasons. First, the district court appears to have interpreted
Ziccarelli I to foreclose a theory of relief based on constructive
discharge. On this basis, it concluded that Ziccarelli could not
claim prejudice resulting solely from his decision to retire.
965 (7th Cir. 2024), in support of this argument, but the plaintiff there
never moved for either judgment as a matter of law or a new trial, making
it quite different from this case.

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22 No. 24-2377
The district court understood us correctly. See Ziccarelli I, 35
F.4th at 1090 (“[E]ven plaintiff’s version of that conversation
falls far short of evidence that could support a claim for con-
structive discharge.”).
Second, the district court did not abuse its discretion by
concluding that Ziccarelli had not presented evidence of prej-
udice aside from his resignation and the resulting harm. It
properly pointed to the one post-conversation day of FMLA
leave as evidence that Ziccarelli did not shy away from taking
leave while he remained employed by the Sheriff’s Office.
And Ziccarelli’s later resignation can be thought of as a non-
interference-related event that precludes a claim of ongoing
prejudice resulting from FMLA interference. See Hickey v. Pro-
tective Life Corp., 988 F.3d 380, 389 (7th Cir. 2021) (affirming
summary judgment when plaintiff suffered FMLA interfer-
ence but was terminated for other reasons before he had “suf-
fered any compensable damages under § 2617(a)(1)(A)(i)”);
Cianci v. Pettibone Corp., 152 F.3d 723, 728–29 (7th Cir. 1998)
(finding as a factual matter that plaintiff who was fired before
she took requested FMLA leave could not demonstrate preju-
dice). Hickey and Cianci boiled down to proof problems:
Hickey and Cianci could not show prejudice for purposes of
their FMLA claims because they did not work at their jobs
long enough to suffer prejudice. The same may well be true in
this case.4
4 The outcome would obviously be different if the termination was
related to the FMLA interference. That is not true of Ziccarelli’s resigna-
tion, see Ziccarelli I, 35 F.4th at 1091 (noting that a reasonable person in
Ziccarelli’s shoes would have “thought he had several options short of im-
mediate retirement”), and apparently was not true of the firings in Hickey

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No. 24-2377 23
We note that the district court has not addressed a theory
of relief that it (and the parties) discussed in the pretrial con-
ferences: whether Ziccarelli might obtain “accrued sick leave
benefits.” Indeed, the Sheriff’s Office appeared to concede
pre-trial that Ziccarelli could seek accrued sick leave benefits
if he otherwise prevailed on the merits. See Dkt. 840 at 4. This
theory presents some of the same problems addressed in
Hickey and Cianci, which are related to the district court’s find-
ing that Ziccarelli has not presented evidence of prejudice. It
is not clear to us how Ziccarelli can claim his unpaid sick time
as a “direct result of the violation” if he is deemed to have
resigned voluntarily, and we do not know whether he might
have had a contractual entitlement to the sick leave. See 29
U.S.C. § 2617(a)(1)(A)(i)(II); Simon, 46 F.4th at 612 (“A plaintiff
cannot collect damages for periods of time in which he other-
wise could not have worked for the company.”). But
Ziccarelli’s theory of how he might obtain accrued sick leave
benefits can be explored on remand. Depending on how per-
suasive that theory is, and whether he can access damages in
the new trial, the court might reconsider its new trial order in
connection with the Sheriff’s Office’s motion for remittitur,
which the court did not reach. JMOL Order, 2024 WL 3740602,
at *3; see also Galvan v. Norberg, 678 F.3d 581, 587 (7th Cir.
2012) (“the district court has the discretionary authority to re-
consider a new trial order.”).5
or Cianci either. See Simon, 46 F.4th at 613 (noting lack of causation in
Hickey).
5 We also take no position on whether the FMLA allows an award of
nominal damages, a question that has not been briefed for us and is not
suitable for non-adversarial resolution. See also Simon, 46 F.4th at 611 n.3

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24 No. 24-2377
* * *
Before we wrap up, a few housekeeping matters are in or-
der. First, Ziccarelli contends that the law-of-the-case doctrine
precludes consideration of the post-phone call day of FMLA
leave. This is clearly wrong. As the district court explained,
the timing issue was “not recognized” at summary judgment
or in the last appeal, JMOL Order, 2024 WL 3740602, at *6, and
we did not address it (regardless of whether Ziccarelli’s time-
sheet was in the appellate record). See Petaluma FX Partners,
LLC v. Comm’r of IRS, 792 F.3d 72, 79 (D.C. Cir. 2015) (“an issue
‘assumed’ by an appellate court in an initial appeal does not
become the law of the case; rather, the ‘law of the case doc-
trine does not apply where an issue was not raised before the
prior panel and thus was not decided by it.’” (quoting
Yesudian ex rel. United States v. Howard Univ., 270 F.3d 969, 972
(D.C. Cir. 2001))). And despite our skepticism in Ziccarelli I
about Ziccarelli’s “efforts” to seek damages resulting from
“snowballing consequences,” we explained that “those issues
need to be sorted out in the district court in the first instance.”
Ziccarelli I, 35 F.4th at 1090. We concluded that he could show
interference, not that he had shown interference. The law-of-
the-case doctrine, therefore, did not govern this issue on re-
mand. See Bradley v. Village of University Park, 59 F.4th 887, 896
(7th Cir. 2023) (expressly or necessarily decided issues are
governed by law-of-case doctrine). The district court carefully
navigated the damages-related questions, adroitly resolving
the parties’ various motions in limine, and its resolution of
those issues did not run afoul of Ziccarelli I.
(declining to address issue); Franzen v. Ellis Corp., 543 F.3d 420, 426 n.6 (7th
Cir. 2008) (same).

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No. 24-2377 25
We also decline to address the various damages-related
motions that the district court did not resolve. These include
the Sheriff’s Office’s motion for remittitur and Ziccarelli’s mo-
tion for equitable relief. The district court did not address ei-
ther motion because it granted judgment as a matter of law
and a new trial in the alternative. Both motions remain open
for the district court’s consideration. See David v. Caterpillar,
Inc., 324 F.3d 851, 864 (7th Cir. 2003) (“We review a district
court’s remittitur under an abuse of discretion standard.”);
see generally Franks v. Bowman Transp. Co., 424 U.S. 747, 770
(1976) (“The fashioning of appropriate remedies invokes the
sound equitable discretion of the district courts.”).
Finally, we also decline to reassign the case under Circuit
Rule 36, which allows us to remand to the same judge for a
retrial. Judge Tharp has a thorough understanding of the rec-
ord and of the various issues that make this case challenging.
His knowledge and understanding will help guide the just
resolution of this case.
The district court’s grant of judgment as a matter of law is
REVERSED. The district court’s conditional grant of a new
trial is AFFIRMED. The case is REMANDED to the district
court for further proceedings consistent with this opinion.

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