Repeat officers and the Fraternal Order of Police
For decades, Chicago’s police misconduct problem has been discussed as a moral crisis, a racial crisis, or a political crisis. All or some of those crises may factor in every case. It is, however, mainly a failure of risk management. That lack of risk management carries a price tag that now runs over a billion dollars. At the center of that failure is the fact City Hall has long preferred not to look at the elephant in the room. A disproportionate share of police misconduct lawsuits and settlements involve a small number of repeat-accused officers who remained on the street far longer than prudent management would allow.
This is neither conjecture, nor is it anti-police rhetoric. It is what Chicago’s own settlement data, investigative reporting, and analyses by outlets such as WTTW and research compiled by the Invisible Institute show: Repeat officer incidents account for a majority of the City’s most expensive settlements. Most police officers are never named in a serious misconduct case. Repeat-accused officers account for a clear majority of them.
The Invisible Institute was founded by Jamie Kalven as a loose coalition of independent journalists focused on issues of race, policing, and power in Chicago’s most marginalized neighborhoods, usually covering the interaction of police officers with public housing residents. The Institute’s big break came when Kalven filed Kalven v. City of Chicago, a lawsuit that successfully argued police misconduct records should be public under the Illinois Freedom of Information Act (FOIA). In 2014, a court agreed, creating a historic precedent for transparency in police data and opening the door to systemic, data-driven oversight.
Let the sunshine in! That is always the biggest disinfectant. Both WTTW and The Invisible Institute lean left politically, but that does not mean all their work should be tossed aside. A healthy dose of skepticism works much better than complete banishment.
Between 2019 and 2024, cases involving officers who appeared in more than one settlement absorbed roughly 60 percent of total misconduct payout costs, according to WTTW’s analysis of City of Chicago data. In 2024 alone, repeat-officer cases accounted for the overwhelming bulk of taxpayer spending on police misconduct. The implication is unavoidable. Chicago’s liability exposure is not evenly distributed across its police force. It is concentrated.
This concentration mirrors what researchers have found in other large police departments throughout the nation, but Chicago’s experience is aggravated by history. For much of the late 20th and early 21st century, the city operated under a disciplinary regime that made early intervention exceptionally difficult. Complaints were routinely labeled “not sustained,” not because misconduct had been disproven, but because it could not be established conclusively in a world without body-worn cameras or reliable civilian video. Officers could accumulate dozens of complaints without ever crossing a disciplinary threshold that triggered meaningful consequences. By the time conduct finally resulted in a major lawsuit or wrongful-conviction claim, the warning signs had often been visible for years.
This is where union protections enter the story, not as a conspiracy, but as a structural amplifier of risk. The Fraternal Office of Police (FOP), like police unions nationwide, negotiates contracts that emphasize due process, progressive discipline, and arbitration. These protections serve an important purpose. Police officers exercise coercive power on behalf of the state, and they deserve safeguards against arbitrary punishment or political retaliation. That is especially true considering the current, demented “defund the police” nonsense. But in Chicago, the balance tipped too far toward insulation and away from risk containment.
Union contracts and arbitration practices historically allowed officers who had been fired or severely disciplined to be reinstated years later, often after memories had faded and supervisors had moved on. Rules limiting how long complaint histories could be retained or considered made it harder to identify long-term patterns. Even when the City of Chicago prevailed in terminating an officer, arbitration frequently reversed those decisions, sending the officer back into active duty with back pay. Each reinstatement extended the City’s exposure window. Each additional year on the street increased the probability that a repeat-accused officer would generate another incident and yet another lawsuit.
It is important to be precise here. Unions do not decide who commits misconduct, who files lawsuits, or how juries rule. They do not negotiate settlement amounts. The worst effect of the FOP is duration: how long an officer with a demonstrated risk profile remains in a position to generate liability. From a fiscal standpoint, that duration matters enormously. A single high-risk officer left in the field for 10 additional years can cost the City more than dozens of policy reforms applied indiscriminately.
The data underscore this point. Complaint records show since 2018, roughly five percent of CPD officers account for more than 30 percent of all complaints. That does not mean those officers are guilty of every allegation lodged against them. But from a risk-management perspective, complaint concentration is exactly the signal that supervisors and departments are supposed to act on. In Chicago, for too long, they could not do so effectively.
The cost of that failure is most visible in wrongful-conviction cases. Many of Chicago’s largest settlements stem from misconduct that occurred decades ago, long before body cameras or modern oversight existed. In case after case, the same names appear in multiple exonerations. These officers were not anonymous rogues. They were known quantities within the department, often generating complaints and internal concern well before their actions led to catastrophic outcomes. Yet the system lacked the tools and sometimes the will to remove them early.
This is why recent reforms, while imperfect, represent a genuine shift. Body-worn cameras have transformed complaint evaluation, collapsing “he said, she said” disputes into objective evidence. Early-warning systems now flag patterns of force, complaints, and pursuits in near-real time. The federal consent decree has forced the department to document, supervise, and intervene in ways that were previously optional. Perhaps most importantly, arbitration outcomes have begun to change, as video evidence makes it harder to overturn discipline.
These reforms do not erase the legacy costs Chicago continues to pay. Lawsuits filed today often arise from conduct that occurred years earlier. Nor do they eliminate the role of unions in shaping disciplinary outcomes, but they do change the calculus. When misconduct is documented clearly and patterns are identified early, union protections become less of a shield for repeat offenders and more of what they were intended to be. That works as safeguards for most officers who do their jobs properly. The probability of the “bad apples” rotting on the withered branch has increased.
From a taxpayer’s perspective, the lesson is straightforward. If Chicago wants to reduce misconduct payouts meaningfully over the next decade, the highest return on investment will not come from sweeping, symbolic gestures. It will come from relentless focus on repeat-risk officers by identifying them early, limiting their exposure, reassigning them when necessary, and removing them when warranted. Every year shaved off the tenure of a high-risk officer produces outsized savings, both financial and human. That next billion dollars can be allotted to putting more police officers on the street or for fiscal relief.
This is not anti-police. It is pro-police professionalism. Most officers will never be named in a serious misconduct lawsuit. They bear the reputational and operational costs of a system that failed to deal decisively with the few who repeatedly crossed lines. Allowing a small cohort of repeat offenders to dominate the City’s liability profile undermines public trust and demoralizes the rank and file.
Chicago’s experience makes one thing clear. Police misconduct is not a diffuse, insoluble problem. It is concentrated, predictable, and manageable if institutions are willing to confront it honestly. The City of Chicago has begun to do so, belatedly despite pressure from the FOP. Whether it sustains that effort will determine whether the next generation of Chicagoans inherits a safer city, or another billion-dollar bill for yesterday’s failures.
