United States Court of Appeals For the Seventh Circuit ____________________ No. 23-2140 JOHN BROOKS and GREGORY SIMMONS, Plaintiffs-Appellants, v. CITY OF PEKIN, et al., Defendants-Appellees. ____________________

Appeal from the United States District Court for the Central District of Illinois. No. 1:18-cv-01334 — James E. Shadid, Judge. ____________________

ARGUED JANUARY 19, 2024 — DECIDED MARCH 8, 2024 ____________________

Before ST. EVE, KIRSCH, and LEE, Circuit Judges. KIRSCH, Circuit Judge. John Brooks (a former police lieuten- ant) and Gregory Simmons (a former police officer) had a his- tory of workplace misconduct while employed by the City of Pekin. Simmons was terminated in March 2018, and Brooks retired in July 2018 in the face of a complaint filed against him with the Fire and Police Commission. Soon after, Brooks and Simmons sued the City and four City employees. Relevant to this appeal, Brooks—who has sleep apnea—brought claims 2 No. 23-2140 against the City under the Americans with Disabilities Act, alleging that it: (1) failed to provide him a reasonable accom- modation when it denied his request to transfer to a different work shift; (2) engaged in disparate treatment by disciplining and constructively discharging him because of his disability; and (3) retaliated against him because he filed several com- plaints related to his accommodation requests. Simmons al- leged that the City retaliated against him in violation of Title VII of the Civil Rights Act of 1964 for reporting allegedly sex- ually harassing comments made by his former boss. The dis- trict court granted summary judgment for the defendants. Brooks only appeals his three claims against the City under the ADA, and Simmons only appeals his one claim against the City under Title VII. They do not appeal their other claims, including those against the individual defendants. Because the district court did not err, we affirm. I John Brooks joined the Pekin Police Department around 1995 and spent most of his early career working the second shift. He began receiving treatment for sleep apnea around 2000. In April 2012, he was promoted to lieutenant and was initially assigned to the third shift. He was transferred to the first shift in November 2013, then back to the third shift in July 2016. Like Brooks, Gregory Simmons also began working for the Pekin Police Department around 1995. In December 2016, then-Lieutenant Greg Burris asked him about his sex life and stated that the woman Simmons was dating had “brain dam- age.” Simmons reported Burris’s comment to Deputy Chief Donald Baxter, and Burris consequently received a two-day suspension. In April 2017, Burris asked Simmons if he was No. 23-2140 3 “fucking that Iraqi,” and Simmons reported the comment to the Chief of Police, John Dossey. Burris was then placed on leave, and later that month, he accepted a last chance agree- ment with a permanent demotion to patrol and a 21-day sus- pension. On May 1, Brooks was transferred to the first shift to re- place Burris. The next day, Brooks impermissibly discussed union issues at a shift brief and asked a male officer whether “the drapes match the carpet.” He received a letter of repri- mand for this conduct. On May 24, Officer Jennifer Melton reported to Baxter that Simmons had made inappropriate comments about her breasts. Melton alleged that Simmons commented on her breasts in front of her husband on March 3, and that on March 25, he made a similar comment to a civilian at a local restau- rant. On June 5, Melton met with the HR Director, S