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CHICAGO — Tom Sherry was hired by the Chicago Police Department in 1997, following in his father’s footsteps.

But he’s spent more than half of his career on desk duty, stripped of his police powers, as a result of his ties to the Special Operations Section, a citywide unit that was tasked with going after high-level gun and narcotics suspects.

“I didn’t sign up to answer phones or write reports,” Sherry said in an interview this month with WGN Investigates. “I signed up to make a difference, wanting to do the right thing for good people. Being part of a bigger scene, a bigger project, I wanted to do good things.”

The SOS was disbanded after it came to light that several officers in the unit were operating as a robbery crew, committing home invasions and stealing hundreds of thousands of dollars from criminal suspects and civilians alike.

Sherry, now 48, was one of 13 SOS officers who faced criminal charges in the scandal. Eleven ultimately pleaded guilty. The charges against Sherry stemmed from a July 2004 narcotics raid at an apartment on the Northwest Side.

In 2009, three years after the charges were filed and he was suspended without pay, the criminal allegations against Sherry and one other officer were dropped.

News reports from that time said the decision to drop the charges was made, in part, because of flawed witness identifications of the two officers. The Cook County State’s Attorney’s Office said the decision was made in consultation with the U.S. Attorney’s Office, which was probing corruption within the CPD. Sherry’s attorney says federal prosecutors even wrote a letter to Sherry, informing him that he was “not a target” of their investigation.

Former CPD Supt. Jody Weis said of the decision to drop the charges: “We have guys who have been in purgatory. It’s time to fish or cut bait … It remains clear that many officers that were assigned to the Special Operations Section were both dedicated and ethical.”

The criminal cases involving the SOS have long since ended. The unit’s ringleader, former officer Jerome Finnigan, was sentenced to 12 years in federal prison in 2011 after he pleaded guilty to a murder-for-hire plot and tax evasion. Federal prison records show he was released from custody more than three years ago.

But the criminal allegations first lodged against Sherry in 2006 now serve as the foundation for administrative charges that the CPD leveled against him in 2020. Nearly 15 years after he was first accused of misconduct, the department wants Sherry fired.

The CPD says Sherry violated several CPD directives, including: breaking the law, disobeying an order and making a false report. The evidentiary hearing that the police board will use to decide Sherry’s fate with the department was initially scheduled to start this week, but it was postponed with no make-up date set yet.

“Everybody else has gone through and done their sentence or been cleared of these allegations and I’m still left here, essentially, holding the bag,” Sherry said.

After the criminal charges were dropped in 2009, Sherry was assigned to the CPD’s Alternate Response Section — known as “callback” — where he’d answer non-emergency phone calls and fill out police reports in a nondescript building on the Near West Side.


“In 2009, when those charges were finally dropped, you’re looking for breathing room, you’re looking to start your life and move forward,” Sherry said. “And knowing that there was a legitimate reason for the charges being dropped, I looked to restart my life again. As hard as that was, there was never any closure to it.”

While at callback — the landing spot for CPD officers who are under investigation or recovering from an on-duty injury — Sherry was barred from carrying a gun, working overtime or holding a part-time job.

“Yes, there are officers that shouldn’t have been on this job that are facing criminal charges for good reason,” Sherry said. “And you’re sitting there among some of them and you’re wearing the scarlet letter. The department looks down on you, the city looks down on you, anybody that’s even read about this investigation just assumes that you are guilty, you’re wrong.”

He filed a lawsuit against the city in 2018, alleging that the lack of a timely investigation was a violation of his rights. A federal judge threw out the lawsuit last March, a few months after Sherry’s police board charges were filed.

Sherry believes the police board charges against him are the CPD’s way of punishing him for filing the lawsuit.

“I think it was done out of malice,” Sherry said. “I think it was done out of spite because I wouldn’t sit quietly and go off into the night.”

A representative for the CPD, citing the ongoing police board case, declined to answer questions about the timing of the police board charges and if Sherry’s lawsuit was a factor.

But still, Sherry is at least partly looking forward to presenting his case to the police board.

“I’m looking to establish myself. But I want my name cleared. That is the most important thing,” he said. “I want [my son] to be able to look forward and say ‘My dad went through this and was able to withstand the hardest part about it and come through.’ I want to be able to move on with my life.”