Even in a city with a notoriously slow police disciplinary process, Officer Thomas Sherry’s case stands out.
Back in 2006, he was stripped of his police powers when charged with felonies in one of Chicago’s biggest police scandals ever — a scandal in which 11 members of CPD’s former Special Operations Section were convicted of crimes including robbing and kidnapping suspected drug dealers.
Sherry’s charges were dropped in 2009 but he remained stripped. For the next 12 years, he worked a CPD desk job and collected his salary, most recently listed at $87,006. In 2020, CPD finally filed disciplinary charges.
Those charges have led to a trial-like Police Board hearing on whether Sherry, 48, should be fired after spending half of his police career behind a desk.
The hearing, to be held over three days this week, is focusing on raids of two Northwest Side homes in which cops allegedly carried out robberies in 2004. The raids included Officer Jerome Finnigan, the reputed ringleader of the corrupt cops, who was arrested with Sherry and eventually sent to federal prison.
Paul Geiger, an attorney for Sherry, said his client played no part in victimizing the people in the homes.
“Were these two gentlemen ripped off? Well, it certainly appears that they were. But they weren’t ripped off by Tom Sherry,” Geiger said.
But police accountability advocates say it took way too long for the city to bring the dismissal case against Sherry.
“Eighteen years after a guy who was involved in routinely breaking into people’s homes and robbing them, he’s finally being held accountable,” University of Chicago law professor Craig Futterman said. “That’s not something to celebrate.”
“The Police Department … refused to connect the dots and, all along the way, the people of Chicago continued to pay a guy, who used his badge to rob them, nearly $100,000 a year,” said Futterman, who brought civil lawsuits for alleged victims of SOS officers years before the public scandal.
Allegations in the dismissal case
Hired by CPD in 1997, Sherry worked for six years in a busy West Side patrol district before he was promoted to rove citywide in an elite mobile unit called the Special Operations Section, according to police records.
As part of SOS, he was at the center of a Chicago strategy of deploying hundreds of cops to the latest gun-violence hotspots in hopes that mass arrests — in the name of combating “gangs, guns and drugs” — would tamp down the shooting.
On July 27, 2004 — two months after he arrived in SOS, according to CPD data — Sherry and other SOS members searched a man’s apartment at 3930 N. California Ave. The officers lacked a warrant or valid consent to search, according to the disciplinary charges against Sherry.
A CPD Bureau of Internal Affairs sergeant concluded Sherry confiscated approximately $12,000–$15,000 and illegal narcotics during that search, according to a Police Board memorandum that summarizes the allegations. The drugs were put into a Nike shoe box, the memo says.
Sherry has denied knowing of any police wrongdoing during incidents that involved him that day.
“Finnigan took this guy into his apartment’s bathroom to talk to him,” said Geiger, Sherry’s attorney. “Finnigan was constantly stealing from people on his own.”
But the board memo says Sherry allegedly coerced the resident into providing another location for money and narcotics in exchange for reduced charges.
Later that day, according to the disciplinary charges, Sherry unlawfully entered a second man’s home, at 2217 N. Harlem Ave., and searched it without a warrant or valid consent.
Sherry, according to the board memo, also allegedly planted evidence against the man in the Harlem Avenue home — the Nike box containing drugs. Sherry then allegedly arrested the man for possession of a controlled substance. Sherry also allegedly confiscated some $5,500 from the home and failed to inventory it.
Sherry, according to the charges, also authored and submitted false reports about the search and arrest and about the recovered narcotics. And he allegedly failed to notify supervisors of misconduct by Finnigan and other fellow SOS members associated with the arrests.
“That makes an assumption that he knew Jerry Finnigan was ripping these guys off,” Geiger said.
In 2006, Cook County prosecutors charged Finnigan, Sherry and two other SOS members with felonies including armed violence, home invasion and kidnapping during a series of incidents.
CPD stripped Sherry of police powers and, later that year, put him on unpaid leave.
The unfolding SOS scandal led CPD to disband the unit in 2007 and helped push then-Police Supt. Philip Cline to retire that year.
In 2009, however, the criminal charges against Sherry and a second officer were dropped because victims could not place those cops at the scenes of the alleged crimes.
Sherry returned to work but without police powers because of possible federal charges and a pending CPD disciplinary investigation.
After criminal prosecutions of SOS members wrapped up in 2013, federal officials turned over evidence from the scandal to the police department.
But the CPD probe seemed to go nowhere — while Sherry, still lacking police powers, remained in a police unit that takes nonemergency calls, an assignment his supporters likened to purgatory.
Kathleen Hill — an attorney who will argue to fire Sherry in the evidentiary hearing this week on behalf of Police Supt. David Brown — declined to comment on the case and its delays.
In 2018, Sherry sued the city in federal court, seeking back pay for lost work opportunities while stripped of police powers and alleging that CPD was violating his due process rights by refusing to hold a “name-clearing hearing” that could return him to regular police duty.
The lawsuit cited a CPD general order that requires “prompt” investigations into misconduct allegations.
“Now that more than 15 years have elapsed from the date of the alleged misconduct in July 2004, and all potential criminal statutes of limitations have long since expired, it is clear that the city of Chicago and its Department of Police will never provide Tom Sherry with a hearing,” the suit claimed.
Criminal crews within CPD
Cops and their attorneys have long criticized delays in discipline cases. So have human-rights advocates and government officials.
The U.S. Department of Justice, in a 2017 evaluation of Chicago policing prompted by teenager Laquan McDonald’s fatal shooting by police, reported that the delays can prevent investigators from uncovering the truth because “memories fade, evidence is lost, and investigators may not be able to locate those crucial witnesses needed to determine whether misconduct has occurred.”
Last month, Chicago police Sgt. Alvin Jones quit CPD upon the release of a long-delayed investigation summary alleging he engaged in extortion in 2005 as part of a crew of corrupt cops led by former Sgt. Ronald Watts. Jones is the only cop to have faced a discipline proceeding in the scandal since Watts and another member of the crew were sent to federal prison after their 2012 arrests.
“It is disgraceful that our system is so labyrinthine, so convoluted, that it takes two decades to bring a police officer to a hearing for this kind of serious misconduct,” said Ronald Safer, a former federal prosecutor who led a 2014 study of the city’s police disciplinary setup.
“But even if it’s 20 years later, even if it’s 40 years later, it needs to be done because police officers cannot get away with this kind of misconduct without consequences,” Safer said. “It has happened too long in the Chicago Police Department. Ignoring that misconduct — allowing it to go unpunished — is what breeds more and more of it.”
Futterman, the law professor, blasted the city for allowing corrupt groups of officers to operate within the Police Department.
“Why wasn’t the city doing the most basic thing, looking into patterns of abuse complaints and actually investigating and using information that a 5-year-old kid could see?” Futterman said.
The DOJ report mentioned the SOS scandal but did not recommend steps to crack down on criminal police groups.
Researchers outside the department recently analyzed decades of public data and identified 160 “potential crews” of deviant cops, some still on the force, they said.
A CPD statement about that analysis says the department has increased compliance with consent decree requirements aimed at “building and strengthening trust within every community across the city.”
The consent decree, a court-enforceable police-reform agreement that stemmed from the DOJ report, requires data analysis and “early intervention systems” to identify “at risk” individuals. But the prescribed interventions consist mainly of wellness efforts for individual officers such as “the opportunity to participate in an initial counseling session.”
This week’s hearing
With Sherry’s lawsuit pending, Mayor Lori Lightfoot’s administration filed the dismissal charges in November 2020. The charges paved the way for this week’s evidentiary hearing — an opportunity for Sherry to clear his name.
But CPD also moved Sherry to “no-pay status” in February 2021.
Geiger, the officer’s attorney, calls the dismissal case “retaliation” for the lawsuit.
“If he had never stood up for himself, he’d still be answering phones,” Geiger said. “There was no investigation.”
In this week’s Police Board hearing, scheduled to run through Wednesday, city lawyers must present a “preponderance of evidence” to win a guilty finding. That means convincing the board there is more than a 50% chance that Sherry committed the alleged rule violation — a lower standard than in criminal trials, which require proof “beyond a reasonable doubt.”
Hearing officer Allison Wood will oversee the proceeding and report to the nine-member board. The hearing is also videotaped for them. The board, likely months later, will announce decisions on whether Sherry is guilty and on the severity of his discipline, if any.
If the board fires Sherry, his lawsuit won’t soften the blow. A federal judge last year ruled that the officer had blown a two-year deadline to bring his claims and threw the case out.
Correction: An earlier version of this story misnamed the attorney representing the police superintendent in the disciplinary hearing. Her name is Kathleen Hill.