by Chuck Sharman

In a settlement signed on May 19, 2026, Illinois’ Cook County agreed to pay $4.5 million to resolve claims filed by the Estate of Michael O’Connor, 33, a detainee who fatally hanged himself in the County’s massive jail on Chicago’s Southwest side on Christmas Day 2023. The County Board then approved the payout at its meeting on June 11, the Chicago Tribune reported.

Before his July 2023 arrest, O’Connor’s mental illness was documented by jailers employed by Sheriff Tom Dart during at least two earlier incarcerations since 2012, when staff with the jail’s contracted healthcare provider, Cermak Health, made similar notes. So it was predictable that they would again place him in the Psychiatric Special Care Unit (PSCU) because of “[b]ehavior related to major mental illness that results in imminent risk or harm to self or others,” as recalled in the complaint later filed on his behalf.

Yet on July 18, just 16 days after he was booked into the lockup, “unknown Cermak and Sheriff[’s] personnel inexplicably transferred [him] … to General Population” in the jail, where he was “provided limited to no mental health treatment or services,” the complaint continued. He steadily began to decompensate. A judge ordered another evaluation on October 18 because O’Connor was “exhibiting obvious signs of a psychiatric crisis” and jailers were “failing to provide him adequate medication, mental health treatment or services while being detained in the General Population.”

But they had already moved to place him in disciplinary segregation, prompting an interview with a Cermak doctor who “failed to initiate any additional mental health interventions or discuss [his] psychiatric crisis with other members of the medical staff or correctional staff to ensure that [he] would be housed in an environment that prevents risks of harm to himself or others.” It wasn’t until six days later, on October 25, that O’Connor was finally returned to the PSCU after a different Cermak doctor “acknowledged that [he] was ‘nonsensical’” when he “indicated he was ‘going to hurt myself if I go back into that cell … I cannot be with that lady’ despite his cellmate being a man”—one of several observed “bizarre behaviors” that also “include[ed] ripping up his mattress and flushing [it] down the toilet.”

The screw turned again just days later, when a third Cermak doctor cleared O’Connor for transfer out of the PSCU once more. His decompensation continued, and by November 14 he began refusing his psychotropic medication. Unsurprisingly, his behavior became increasingly disruptive. Equally unsurprising, guards responded by moving to place him in disciplinary segregation. Still another Cermak doctor evaluated him for the transfer and approved it— “[d]espite actual knowledge of [his] persistent psychosis, repeated refusal to take his psychotropic medication, and prior threats of suicide,” the complaint said.

Guards continued to respond to O’Connor’s suicide threats by asking to place him in disciplinary segregation, which Cermak staffers continued to approve. When Christmas Day arrived and the jail suffered an entirely foreseeable outbreak of guards calling out “sick,” those remaining on duty instituted a lockdown, keeping detainees in their cells to be “cross-watched” by a single guard covering two housing units. The guard monitoring O’Connor’s unit failed to make required checks every 30 minutes, however; he was then found unresponsive and hanging from a bedsheet. Emergency lifesaving measures failed, and he was pronounced dead that day.

With the aid of attorney Michael L. Gallagher of his eponymous Chicago firm, O’Connor’s sister, Maria Baba, filed suit as personal representative of his Estate in state Circuit Court for Cook County in 2024. Pursuant to 42 U.S.C. § 1983, the complaint accused the County, its Sheriff, Cermak and various personnel of deliberate indifference to O’Connor’s serious risk of harm, in violation of his civil rights. Additional claims were lodged under the state Wrongful Death Act. The parties then proceeded to reach their settlement agreement. Under its terms, the County paid $4.5 million to settle all the Estate’s claims, including cost and fees for its attorney. See: Baba v. Cook Cty., Ill. Cir. (Cook Cty.), Case No. 2024L003693.

It was reportedly the largest settlement paid by the County for a complaint filed on behalf of a pretrial detainee, dwarfing the $1.85 million paid in 2025 to Eugene Westmoreland, 64; as PLN reported, he was left permanently confined to a wheelchair by a fall from his cell’s upper bunk in 2023, after jailers neglected to make sure he was assigned to a lower bunk to accommodate extreme weakness in his legs resulting from a childhood bout of polio. The County earlier paid $1.5 million to settle claims filed on behalf of Areon Marion, 22, another pretrial detainee who fatally hanged himself in October 2021. [See: PLN, Dec. 2025, p.30; and Nov. 2024, p.57.]

Gallagher, who helmed the Torts and Civil Rights Section at the Cook County State’s Attorney’s Office from 2012 to 2015, said that “I don’t know what happened over the last several years” at the Sheriff’s Office, which at the time he left “had made significant strides in staffing and policies.” But he said that the rising number of jail deaths—which reached 18 in 2023, the year that O’Connor died—was “more than alarming.”  

Additional source: Chicago Tribune

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