Chicago police misconduct costs keep soaring with proposed $35 million in deals

Jake Sheridan, Chicago Tribune on Jul 10, 2025

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CHICAGO — Chicago’s record spending on police misconduct settlements is likely to climb higher this month with another $35.2 million in proposed deals, most tied to decades-old wrongful conviction cases featuring disgraced detectives.

City attorneys are recommending aldermen settle up to avoid even larger court payouts in five cases. if approved, the payments will exacerbate the city’s looming budget problems.

The City Council and Mayor Brandon Johnson have already approved a record $206 million in such deals this year, an amount that towers over both the budgeted $82.6 million and year-end totals from the past. That sum includes $19 million to be paid by the city’s insurers, but not another $120 million from two court verdicts the city plans to contest.

Aldermen are set to vote on the deals Monday in a Finance Committee meeting, clearing the way for a possible final vote Wednesday by the full City Council.

July’s largest proposed deal would send $17,000,000 to Roberto Almodovar, convicted in 1995 of a double homicide. Eyewitness reports obtained in part by infamous Detective Reynaldo Guevara tied him to the shooting.

The Humboldt Park man spent decades in prison before a judge tossed his conviction when prosecutors abandoned the case. He received a certificate of innocence in 2017.

Almodovar’s lawsuit against the city accuses Guevara, similarly accused in dozens more cases, of framing Almodovar with coerced and manipulated confessions. Guevara and his partners had long harassed Almodovar, who was loosely affiliated with the Insane Dragons street gang around the time, according to the lawsuit.

“Their perspective was that all the ‘gang bangers’ in Humboldt Park were the same and would eventually get what was owed to them, either death or murder charges,” the lawsuit said.

Aldermen could also award Jackie Wilson a $12,700,000 deal after he was allegedly tortured and framed for a shooting his brother committed.

Wilson was driving a car and complying with police commands when his brother shot and killed two officers during a 1982 traffic stop. Police led by Cmdr. Jon Burge extracted a false confession from Wilson by beating him and torturing him with electrical shocks, according to Wilson’s lawsuit.

The charges against Wilson were dismissed in 2020, and he won a certificate of innocence months later. He also won a $17 million payout from the Cook County Board last year.

Johnson’s Law Department also recommends aldermen give a $3 million settlement to a man who was allegedly intentionally hit by a police car and severely injured while on foot during a chase, as well as $2.5 million for the father of two young children who police pointed guns at while executing a search warrant at the wrong house.

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