Anjenai Bolden v. Wyatt Risley

United States Court of Appeals
For the Seventh Circuit
Chicago, Illinois 60604
Submitted November 13, 2025*
Decided November 14, 2025
Before
MICHAEL B. BRENNAN, Chief Judge
DIANE S. SYKES, Circuit Judge
AMY J. ST. EVE, Circuit Judge
No. 22-1670
ANJENAI BOLDEN,
Plaintiff-Appellant,
v.
WYATT RISLEY, et al.,
Defendants-Appellees.
Appeal from the United States District
Court for the Central District of Illinois.
No. 19-3067
Colin S. Bruce,
Judge.
O R D E R
Anjenai Bolden, an Illinois prisoner convicted of criminal sexual assault, alleges
that prison officials instigated harassment against him and failed to protect him from
harm in violation of his rights under the Eighth Amendment. See 42 U.S.C. § 1983. The
district judge entered summary judgment for the defendants because Bolden’s claims
* We have agreed to decide the case without oral argument because the briefs and
record adequately present the facts and legal arguments, and oral argument would not
significantly aid the court. F ED. R. A PP . P. 34(a)(2)(C).
NONPRECEDENTIAL DISPOSITION
To be cited only in accordance with F ED. R. APP . P. 32.1

-- 1 of 3 --

No. 22-1670 Page 2
were untimely and because he failed to adduce evidence upon which a jury could have
returned a verdict in his favor. We affirm.
We construe the evidentiary record in the light most favorable to Bolden, the
nonmoving party. Moore v. W. Ill. Corr. Ctr., 89 F.4th 582, 590 (7th Cir. 2023). According
to Bolden, prison officials at Western Illinois Correctional Center in Mount Sterling,
Illinois, told various prisoners that he was a sex offender, and as a result those prisoners
harassed him. Bolden filed a grievance, which the Administrative Review Board denied
as untimely on January 12, 2017. On March 6, 2019, Bolden filed in the district court
what he called a motion for an extension to file a complaint, which the judge construed
as a complaint. Bolden then filed a first amended complaint on October 15, 2019,
detailing threats from other prisoners and alleging inaction from the defendants.
Bolden moved to further amend his first amended complaint in March 2021 and
February 2022. The judge denied the first motion because discovery had closed a month
earlier and Bolden had not attached a proposed amended complaint as the scheduling
order required. He denied the second after concluding that permitting Bolden to amend
his complaint at that late stage of proceedings would cause undue delay and would
prejudice the defendants because the proposed complaint included more than 60 new
defendants and alleged various harms taking place over a period of more than five
years.
Bolden also requested the assistance of counsel. After denying the first two
requests, the judge granted Bolden’s third motion to recruit counsel because Bolden had
injured his hand, making it difficult to write, and because Bolden lacked adequate
access to the law library and his legal property. The judge advised Bolden, however,
that finding counsel was not guaranteed and that he should continue trying to litigate
the case on his own. The judge contacted 30 attorneys individually, as well as a bar
association, but was unable to recruit counsel.
In granting summary judgment for the defendants, the district judge concluded
that the two-year statute of limitations for § 1983 claims in Illinois barred Bolden’s suit.
The judge reasoned that the latest Bolden could have filed his complaint was
January 12, 2019, two years after he exhausted the prison’s grievance process. Bolden’s
March 6, 2019, filing was therefore untimely. Regardless, the judge determined that
there was insufficient evidence that the prison officials failed to protect Bolden.
Bolden argues that the judge erred in concluding that his claim was time-barred.
But he does not challenge the judge’s conclusion that no reasonable jury could have

-- 2 of 3 --

No. 22-1670 Page 3
found that the defendants failed to protect him. Because Bolden’s opening brief does
not engage with the underlying substantive claim, he has waived any challenge to this
dispositive issue. See Reed v. Freedom Mortg. Corp., 869 F.3d 543, 548 (7th Cir. 2017)
(“When a district court gives two independent, dispositive reasons for ruling against a
party, and the party challenges only one of those grounds, any challenge to the alternate
basis is waived and we may affirm.” (internal quotation marks omitted)).
Bolden next challenges the denial of his two motions for leave to amend his
complaint. Leave to amend is freely granted when justice so requires. F ED. R. C IV.
P. 15(a)(2). But district courts have broad discretion to deny leave to amend for undue
delay or prejudice to the defendants. Mulvania v. Sheriff of Rock Island Cnty., 850 F.3d
849, 855 (7th Cir. 2017). Here, the first motion for leave to amend was filed a month after
discovery closed and 17 months after Bolden filed his first amended complaint. Bolden
also failed to attach a proposed second amended complaint as the scheduling order
required. We see no abuse of discretion in denying a motion for leave to amend filed
nearly a year and a half after the first amended complaint and out of compliance with
the court’s scheduling order. See Smart v. Local 702 Int'l Bhd. of Elec. Workers, 562 F.3d
798, 811 (7th Cir. 2009).
The judge properly denied the second motion, filed nearly a year after the first,
because it would have unduly prejudiced the defendants and delayed the proceedings
by adding over 60 defendants alleged to have participated in events spanning more
than five years. See Mulvania, 850 F.3d at 855 (affirming a denial of a motion for leave to
amend that would have prejudiced the defendants by requiring substantial additional
discovery). Further, many of the proposed additional claims were unrelated to the
allegations in the first amended complaint and to each other. The likelihood of
misjoinder further supports the judge’s decision. See Flowers v. Kia Motors Fin., 105 F.4th
939, 945 (7th Cir. 2024).
Finally, Bolden asserts that the court prejudiced him by denying his first two
motions to recruit counsel. But the judge granted the third such motion, mooting the
denials of the first two, and was simply unable to find a volunteer. District courts are
not required to search for pro bono counsel indefinitely, and the court’s efforts here
were more than adequate. See Austin v. Hansen, 139 F.4th 604, 605–06 (7th Cir. 2025).
AFFIRMED

-- 3 of 3 --