JAMES E. ENGSTROM and RICHARD SHAW v. United Airlines, Inc.

United States Court of Appeals
For the Seventh Circuit
Chicago, Illinois 60604
Argued September 16, 2025
Decided June 1, 2026
Before
THOMAS L. KIRSCH II, Circuit Judge
CANDACE JACKSON-AKIWUMI, Circuit Judge
NANCY L. MALDONADO, Circuit Judge
No. 25-1039
JAMES E. ENGSTROM and RICHARD
SHAW,
Plaintiffs-Appellants,
v.
UNITED AIRLINES, INC.,
Defendant-Appellee.
Appeal from the United States District
Court for the Northern District of
Illinois, Eastern Division.
No. 1:23-cv-15792
Matthew F. Kennelly
Judge.
O R D E R
James Engstrom and Richard Shaw (“Plaintiffs”) are pilots for United Airlines
who received religious exemptions from United’s vaccine policy during the COVID-19
pandemic. United placed them on unpaid leave to accommodate the exemption, and
they later sued, alleging that this practice amounted to religious discrimination. After
the district court dismissed their second amended complaint, which asserted claims
against United under the Florida Civil Rights Act and state common law, Engstrom and
Shaw moved for leave to file a third amended complaint. Their proposed complaint
NONPRECEDENTIAL DISPOSITION
To be cited only in accordance with F ED. R. APP . P. 32.1

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asserted, for the very first time in the nearly two-year litigation, claims under Title VII
against United. The district court denied the motion and dismissed the case, citing
undue delay and prejudice as well as futility of the proposed amendment. Engstrom
and Shaw appeal that decision. On the unique facts of this case, we see no abuse of
discretion, so we affirm.
I
During the COVID-19 pandemic, United Airlines implemented a vaccine policy
that required employees to receive at least one dose of the COVID-19 vaccine by
September 27, 2021. Employees who did not receive the vaccine and who were not
exempted would be fired. And employees who received exemptions would be required
to take unpaid leave indefinitely, without benefits. Engstrom and Shaw, both
Christians, sought and received a religious exemption from the requirement and then
were placed on unpaid leave, lasting several months, as an accommodation.
While on leave in December 2021, Engstrom and Shaw, who live in Florida, each
filed charges against United with the Florida Commission on Human Relations
(“FCHR”) and the Equal Employment Opportunity Commission (“EEOC”), alleging
discrimination and retaliation under Title VII of the Civil Rights Act of 1964, 42 U.S.C.
§ 2000e, et seq., and the Florida Civil Rights Act (“FCRA”), Fla. Stat. § 760.01, et seq. The
next month, they also filed charges of discrimination with the EEOC and the FCHR
against their union, Air Line Pilots Association International.
In November 2022, after receiving a right-to-sue notice from the EEOC with
respect to their charges against the union, Engstrom and Shaw sued the union and the
United Airlines Master Executive Council (a chapter of the union for United
employees)—but not United—in the Middle District of Florida. That complaint against
the union and council alone alleged violations of, among other things, both the FCRA
and Title VII. Five months later, in April 2023, Engstrom and Shaw filed an amended
complaint, adding United as a defendant and removing the council. In this complaint,
Engstrom and Shaw only raised state law claims (FCRA and Florida common law)
against United, but continued to assert both Title VII and FCRA claims against the
union. United and the union separately moved to dismiss the complaint on various
grounds, and both argued venue was not proper in the Middle District of Florida. The
district court agreed and, in November 2023, transferred the case to the Northern
District of Illinois.

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No. 25-1039 Page 3
The EEOC then issued a right-to-sue notice with respect to the charges against
United, giving the Plaintiffs until March 19, 2024, to file any Title VII claims against
their employer. The next month, with leave of the district court, Engstrom and Shaw
filed a second amended complaint, again raising claims against both United and the
union. But notably, Engstrom and Shaw failed to add a Title VII claim against United at
that time, continuing to press only claims under the FCRA and state common law.
(Meanwhile, they continued to include Title VII claims against the union.) United and
the union again moved to dismiss, and the district court granted those motions on
various grounds. The court gave Engstrom and Shaw one more chance to move for
leave to amend and submit a proposed amended complaint that stated at least one
viable claim over which it had jurisdiction.
Engstrom and Shaw timely submitted a proposed third amended complaint on
August 26, 2024. This time, they switched course entirely—alleging a Title VII violation
for the first time against United and dropping the union and all other claims from the
lawsuit. United opposed the motion, arguing that it was “an exercise in futility” and
that the “inexcusable delay in asserting their Title VII claims will prejudice United by
forcing it to defend against claims that are both baseless and barred.”
The district court denied leave to amend and dismissed the case. It first
explained that the Title VII claims were not time barred because they related back to the
date of the original pleading. But, it continued, Engstrom and Shaw could have raised
these claims in their second amended complaint, made no attempt to explain why they
failed to do so even after United “took [them] to task” on this issue in briefing, and
offered a “less than satisfactory” explanation (that they were seeking the greater
remedies available under the FCRA) when pressed by the court at a hearing. The court
expressed that “there was and is absolutely no sound reason for plaintiffs not to include
parallel Title VII claims against United in their second amended complaint, particularly
when they asserted such claims against [the union].” The court also observed that the
Plaintiffs “then waited five months past the limitations period for bringing Title VII
claims before they sought leave to amend to add those claims.” The court recognized
that, on its own, a delay in raising a new claim may not be a sufficient reason to deny a
motion for leave to amend, citing Dubicz v. Commonwealth Edison Co., 377 F.3d 787, 793
(7th Cir. 2004), but concluded that the facts here also showed prejudice. Specifically, the
court explained that it was “unfair to United to have to defend over a two-year period
against serial complaints in which [P]laintiffs essentially pull out of a grab bag
whatever claims seem most convenient at the time.” Finally, and in the alternative, the

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court concluded that the proposed amendment would be futile because it did not pass
the threshold of plausibility.
Engstrom and Shaw now appeal.
II
We review the denial of a motion for leave to amend for an abuse of discretion,
McCoy v. Iberdrola Renewables, Inc., 760 F.3d 674, 684 (7th Cir. 2014), overturning if there
is no “justifying reason” for the decision, Access Living of Metro. Chi. v. Uber Techs., Inc.,
958 F.3d 604, 616 (7th Cir. 2020) (quoting Perrian v. O’Grady, 958 F.2d 192, 194 (7th Cir.
1992)). As a general matter, federal courts “should freely give leave [to amend a
pleading] when justice so requires,” F ED. R. CIV. P. 15(a)(2), but that does not mean they
must always do so. “[D]istrict courts have broad discretion to deny leave to amend
where there is undue delay, bad faith, dilatory motive, repeated failure to cure
deficiencies, undue prejudice to the defendants, or where the amendment would be
futile.” Arreola v. Godinez, 546 F.3d 788, 796 (7th Cir. 2008); see Foman v. Davis, 371 U.S.
178, 182 (1962). In our review, we recognize that the district court is “particularly well-
situated to judge the worthiness of a plaintiff’s motion to amend his complaint, having
been involved in the progress of the case throughout its development and having
viewed first-hand the party’s diligence or lack thereof.” Bohen v. East Chicago, 799 F.2d
1180, 1185 (7th Cir. 1986). The question is not whether we would have “come to a
different conclusion than the trial judge,” id., but whether “no reasonable person could
agree with [the] decision,” Schor v. City of Chicago, 576 F.3d 775, 780 (7th Cir. 2009).
The district court denied leave to amend here because (1) the Plaintiffs’ tactics
caused undue delay and prejudice to United, and, in the alternative, (2) amendment
would be futile. We affirm on the first basis, so we do not reach the court’s alternative
holding of futility. With respect to the court’s primary holding, Engstrom and Shaw
argue that the decision “lacks legal and factual support,” insisting that the delay was
“largely irrelevant” and that there was no prejudice to United.
We acknowledge that findings of undue delay at the pleading stage are
“unusual,” and the issue “generally arises when a plaintiff seeks leave to amend deep
into the litigation.” McCoy, 760 F.3d at 687. This is because “[t]he underlying concern is
the prejudice to the defendant rather than simple passage of time.” Id.; see also Park v.
City of Chicago, 297 F.3d 606, 613 (7th Cir. 2002) (noting that “the degree of prejudice to
the opposing party is a significant factor in determining whether the lateness of the

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request ought to bar filing”) (quoting Doherty v. Davy Songer, Inc., 195 F.3d 919, 927
(7th Cir. 1999)); Dubicz, 377 F.3d at 793 (“Delay must be coupled with some other
reason. Typically, that reason . . . is prejudice to the non-moving party.”). But “unusual”
does not mean impossible, and this is not the first time we have upheld the denial of
leave to amend at the pleading stage. See, e.g., McCoy, 760 F.3d at 687; Doe v. Howe
Military Sch., 227 F.3d 981, 989–90 (7th Cir. 2000). Though “we approach the concept of
undue delay at the pleading stage with some skepticism,” on the unique facts of this
case, we conclude that the district court acted within its discretion. McCoy, 760 F.3d at
687.
First, the district court reasonably concluded that United faced prejudice if the
Plaintiffs’ motion were granted. The court’s observation that it would be “unfair” to
make United continue to defend against the Plaintiffs’ “grab bag” approach does not
reflect an abuse of discretion. By the time the Plaintiffs submitted their proposed third
amended complaint, United had already briefed two motions to dismiss, including one
in which the Plaintiffs could have added—but didn’t—Title VII claims against it. So
even though the litigation had not progressed past the pleadings, United “had already
invested significant resources in the case.” McCoy, 760 F.3d at 687. And this can be
indicative of undue prejudice. See id.; see also Airborne Beepers & Video, Inc. v. AT&T
Mobility LLC, 499 F.3d 663, 667 (7th Cir. 2007) (finding prejudice where defendant had
already incurred “significant cost[s]” in briefing three motions to dismiss).
Second, the district court reasonably considered that Engstrom and Shaw could
have asserted their Title VII claims against United in their second amended complaint—
after all, they received notices of their right to sue United forty days before they filed
that complaint. Instead, they chose not to plead a Title VII claim against United (but
only against the union) and proceeded only under the FCRA and state common law. It
wasn’t until seven months later (five months past the filing deadline for the claim), and
after the second amended complaint was dismissed, that they first attempted to assert
the Title VII claims against United. And, as they later admitted, they did so because the
FCRA offered greater remedies. This strategic decision to forego raising claims that
were known and available supports the district court’s decision to deny leave to amend.
See Park, 297 F.3d at 613 (affirming denial where plaintiff sought leave to amend six
months after knowing of a claim she could have brought); George v. Kraft Foods Global,
Inc., 641 F.3d 786, 791 (7th Cir. 2011) (noting that waiting until after document
production to seek leave to amend in order to avoid seeking leave more than once
“does not excuse [the] belated assertion of the claims [plaintiffs] knew about since
nearly the beginning of the case”); see also Glatt v. Chi. Park Dist., 87 F.3d 190, 194

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(7th Cir. 1996) (explaining that in deciding motion for leave to amend, the
“court . . . should consider . . . whether the claim could have been added earlier”).
Third, and relatedly, the district court was rightly and reasonably concerned
about gamesmanship. The court considered that Engstrom and Shaw had “presented no
excuse for omitting” their Title VII claims from the second amended complaint—in fact,
even when United flagged this omission in opposing the proposed amendment,
Engstrom and Shaw were silent in their reply. See McCoy, 760 F.3d at 687 (affirming
denial where plaintiff failed to assert various theories in its earlier pleading and then,
without explaining the delay, attempted to amend the pleading six months after the
original was dismissed); Perrian, 958 F.2d at 195 (affirming denial where plaintiff “ha[d]
not explained why he waited” three and a half months to add additional defendants).
And the explanation they eventually gave when pressed by the district court—that the
FCRA offered greater remedies than Title VII, which contains compensatory damages
caps—“looks more like procedural gamesmanship than legitimate ignorance or
oversight.” McCoy, 760 F.3d at 687; see also Allen v. Brown Advisory, LLC, 41 F.4th 843,
854 (7th Cir. 2022) (considering that the proposed amendment “look[ed] more like an
effort to keep [defendant] locked in litigation rather than an understandable delay
beyond [plaintiff’s] control”); Howe Military Sch., 227 F.3d at 990 (“[P]leading is not like
playing darts: a plaintiff can’t keep throwing claims at the board until she gets one that
hits the mark.”).
We also observe that the tactics used by the Plaintiffs here—intentionally and
unnecessarily delaying the assertion of certain claims for strategic reasons—can be
burdensome to the judicial system and can impair the “public’s interest in speedy
resolution of legal disputes.” Perrian, 958 F.2d at 195. Such burdens “can justify a denial
of a motion to amend ‘even if the amendment would cause no hardship at all to the
opposing party.’” Id. (quoting Tamari v. Bache & Co. S.A.L., 838 F.2d 904, 909 (7th Cir.
1998)).
In short, the district court properly considered the unique facts of this case,
reasonably determined that the Plaintiffs should not be permitted to amend their
complaint a third time, and did not stray from the law in doing so. We affirm.

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