Chicago

City Hall Ready To Cut $15.4M Check To Man Chicago Locked Up For 33 Years

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Published on December 02, 2025
City Hall Ready To Cut $15.4M Check To Man Chicago Locked Up For 33 YearsSource: Unsplash/Tingey Injury Law Firm

City lawyers want Chicago to sign off on a $15.4 million payout to Robert Smith, the man who spent 33 years in prison for a 1987 double murder that a court later wiped from his record. The City Council’s Finance Committee is set to weigh the proposed settlement of his 2021 federal lawsuit this week, with a final vote by the full council potentially landing on Dec. 10.

Attorneys for the city say the $15.4 million recommendation would close out Smith’s civil case and add to a mounting stack of costly settlements tied to old Chicago police investigations. According to WTTW News, if this deal goes through, Chicago’s 2025 tab for similar wrongful conviction and misconduct cases would climb to about $204.6 million.

Records Show Discrepancies In Officer Testimony

Smith’s legal team points to newly surfaced police attendance logs and internal records that they say blow a hole in key trial testimony. Those documents indicate that then Lt. Philip Cline was not on duty on the day investigators claimed Smith confessed, a conflict that Smith’s lawyers argue undercuts Cline’s account on the witness stand. The lawsuit leans on the Illinois Torture Inquiry and Relief Commission’s 2013 finding that Smith’s abuse allegations were credible, noting that prosecutors moved to vacate his conviction in October 2020 and a court later granted him a certificate of innocence. As reported by the Illinois Answers Project, those internal records form a core piece of Smith’s civil claim.

Allegations Of Abuse And Weak Physical Evidence

The suit describes a brutal 19 hour interrogation in which Smith says he was beaten, kicked, choked and mocked, and that officers shoved his wallet and handkerchief into his mouth. His attorneys also argue that no physical evidence connected him to the killings. WTTW News reports that the detectives named in Smith’s case were trained by former Commander Jon Burge, whose legacy of abuse continues to haunt Chicago. One detective who testified, William Pederson, later pleaded guilty to selling confidential records, while another, Robert Rice, has since died. Smith’s lawyers say that backdrop helps explain why prosecutors ultimately agreed to vacate his conviction.

Settlement Talks Stalled By Competing Narratives

For a moment, it looked like both sides were ready to put the case to bed. Federal court filings show that lawyers told a judge earlier this year they had reached a deal, and a July trial date was pulled from the schedule while they worked out final settlement language. But city attorneys have continued to mount a strong defense of the officers named in the lawsuit and have argued in court papers that Smith was guilty and that additional forensic testing could back up that position, according to Chicago City Wire.

What’s Next And The Price Tag

The Finance Committee is expected to take up the proposed settlement this week. If alderpersons send it to the full council and the Dec. 10 vote goes in Smith’s favor, the payout would be finalized. The case highlights the costly and politically fraught choices Chicago faces as it continues to reckon with Burge era misconduct. Advocates for survivors argue that long legal battles only pile on harm and drive up bills for taxpayers, while city lawyers say a vigorous defense is necessary when facts are disputed. The wider context of those choices, along with the attendance logs cited in Smith’s complaint, is detailed in coverage by the Illinois Answers Project.