Chicago City Wire

Jackie Wilson, convicted twice for his role in the 1982 murders of two Chicago police officers, is on his way to receiving a $12.7 million settlement from the city of Chicago stemming from his wrongful conviction lawsuit filed in federal court in June 2021. Council approved the payout on Wednesday, after its Finance Committee on Monday recommended the payment. 

In March 2024, Wilson received a $17 million settlement from Cook County. Both former Cook Co. prosecutors and Chicago Police officers were named in Wilson’s federal lawsuit. For the 65-year-old Wilson, and his attorneys, Loevy & Loevy and the People's Law Office, the nearly $30 million total settlement is one of the largest ever stemming from a wrongful conviction lawsuit.

Along with his brother Andrew, Jackie Wilson was convicted in 1983 of the murders of officers William Fahey, 34, and Richard O’Brien, 33, on a South Side street. In 1989, Jackie was tried separately from his brother and convicted again. Andrew died in prison in 2007.

Fahey (right) and O'Brien (left) | Facebook

In 2015, the Torture Inquiry & Relief Commission (TIRC) referred Jackie's case for a new evidentiary hearing based on Wilson’s claims of police torture. It was then that he became what former Chicago FOP spokesman and author of the column Crooked City, Martin Preib, called the “crown jewel” of the exoneration movement.

In 2018, Cook County Judge Williams Hicks ordered Jackie’s release from prison, and approved a new trial.

During the 2020 trial, Wilson's third—all charges were dropped citing accusations against a former Cook County prosecutor, Nick Trutenko—accusations that were later proven false in a criminal trial.

The city has paid out over $1.1 billion in police related lawsuit settlements since 2008, and Ald. Ray Lopez (15th Ward) is becoming an increasingly vocal critic of the lawyers cashing in on the settlements at taxpayers’ expense.

“It has become a cottage industry, pinstripe patronage,” Lopez told Chicago City Wire for an earlier story, referring to the millions lawyers have pocketed from their share of the settlements.

“In one eight-million-dollar settlement, outside counsel [representing the city] got two million after they said they couldn’t get the witnesses to retry the case,” he said. “Why didn’t they come to this conclusion earlier in the process before their fees piled up.”

Many of the settlements stem from wrongful conviction suits where the settlement amounts are rubber-stamped by Chicago’s Corporation Counsel, and again by City Council’s Finance Committee and finally by the full Council.

“We have to learn to start saying ‘no,’” Lopez said. 

He now fears that the lawyers are pivoting to sue the city for injuries causes by “Acts of God,” injuries the city should not be responsible for.

He cited a $3.5 million payout to a man injured in February in Uptown by the collapsing of a dead tree. The man’s lawyers argued that the city should have known that the tree was in danger of collapsing.

“We’re expanding the bike paths in the city,” he noted. “What happens if a biker falls and gets injured. Is that going to be the city’s fault too.”