Bypassing the Constitution: How Qualified Immunity Enables Repeat Misconduct in Chicago
Natalia Poplawski
Every year, American taxpayers fund bills for police misconduct settlements that cost cities millions; however, the officers responsible face little to no personal consequences. In Chicago, in April of 2026, the city had already spent at least $175.6 million [1] to resolve police misconduct lawsuits, absorbing the financial damages while the individual officers are free from this liability. This strains not just the city budget but also the relationship between misconduct and accountability, which is allowing the same officers to repeat the same violations without deserved consequences.
Qualified immunity, as currently applied in high-misconduct jurisdictions like Chicago, fails to deter repeat constitutional violations and must be reformed. This Article examines what qualified immunity is, the role it plays in judicial decision-making, and how it affects courts' willingness to adjudicate constitutional violations before granting immunity. The Article examines how the doctrine of qualified immunity has evolved from Pierson v. Ray [2] through Pearson v. Callahan, [3] which allowed courts to bypass constitutional questions entirely. The second part examines the Chicago Police Department as a case study and analyzes how qualified immunity weaves into the city’s documented misconduct patterns. The third part of the article then demonstrates that Chicago’s settlement data is not incidental but a direct product of the catch-22, a cycle in which constitutional questions go unanswered, precedents go undeveloped, and repeat violations therefore go unchecked. It argues that restoring the mandatory two-step sequencing of Saucier v. Katz [4] is the most legally grounded path to breaking that cycle.
The Doctrine Defined and its Doctrinal Evolution
Qualified immunity is a judicial doctrine that shields government officials, including law enforcement officers, from civil liability under 42 U.S.C. § 1983 [5] unless their conduct violates a “clearly established” statutory or constitutional right of which a reasonable person would have been aware. The doctrine was first formally articulated in Harlow v. Fitzgerald (1982), [6] where the Supreme Court shifted from a subjective to an objective standard for immunity, severing the requirement that plaintiffs prove an officer acted in bad faith. This shift significantly raised the bar for plaintiffs who seek to hold law enforcement accountable for wrongdoing.
The doctrine’s roots trace back to Pierson v. Ray (1967), [7] where the Court first recognized a good-faith defense for officers sued under § 1983. Over the following decades, the Court slowly expanded the doctrine’s protections, which, in Pearson v. Callahan (2009), [8] granted courts the discretion to bypass the constitutional question entirely and grant immunity without first having to determine whether a constitutional violation had occurred. Before Pearson, the Court in Saucier v. Katz [9] (2001) had ordered a two-step sequential inquiry, where courts were first required to determine whether a constitutional violation occurred, and after that assess whether the right was clearly established. However, Pearson took away this sequencing, allowing courts to dispose of cases on immunity grounds alone, which leaves constitutional questions not only unanswered but also underdeveloped in case law.
Taylor v. Riojas and the Catch-22 of Qualified Immunity
The consequences of allowing courts to bypass the constitutional question entirely are most visible in the doctrine’s central paradox. For a right to be “clearly established,” there has to be a precedent, typically a court decision that specifically recognizes the right in a similar factual context. But because Pearson allows courts to skip the constitutional question, the precedent is rarely created. Therefore, officers are granted immunity because no prior case established the right, and no prior case establishes the right because courts keep granting immunity. Empirical research has shown that officers are not actually notified of the case holdings that are supposed to “clearly establish” the law. This means the doctrine’s central assumption does not hold in practice, being a self-reinforcing cycle where the doctrine falls both theoretically and empirically. This has to be known as the qualified immunity catch-22. [10]
Taylor v. Riojas (2020) represents one of the rare moments the Supreme Court did not follow this cycle. There, officers confined Taylor, a Texas inmate, for roughly four days in a cell covered in 'massive amounts' of human feces, where he did not eat or drink for fear of contamination. [11] They then moved him to a frigidly cold cell with no bunk and a clogged floor drain overflowing with raw sewage, where he was confined without clothing. The Court deemed that qualified immunity was not appropriate and that no officer could have reasonably believed that the conditions of the cells were constitutionally permissible, regardless of whether a prior case was factually identical. That the Court needed to intervene to establish that human beings cannot be housed in cells overflowing with feces shows how far the “clearly established” standard had drifted from basic constitutional common sense. Taylor did not abolish qualified immunity, but instead showed the absurdity of a doctrine that had, in practice, required near-factual precedent before officers could be held accountable for obvious constitutional violations. [12]
The structural problem deepens when qualified immunity is considered alongside the framework of municipal liability established in Monell v. Department of Social Services (1978). [13] Under Monell, municipalities can be liable for constitutional violations resulting from official policy or custom, but the standard is demanding. Plaintiffs have to demonstrate a direct causal link between a municipal policy and the violation, which is difficult to establish and often results in the city, not the officer, bearing the financial responsibility even when suits succeed.
The result of this is a moral hazard, where cities absorb the cost of misconduct through settlement payouts, officers face no personal financial consequence, and the incentive structure is never corrected. In jurisdictions with high misconduct rates, this dynamic is not the exception but the norm. Municipal liability under Monell was meant to ensure institutional accountability, but in practice, combined with qualified immunity’s protection of individual officers, it has protected the entire system from meaningful consequences. This perpetuates a cycle in which taxpayers pay, officers keep offending, and the system repeats itself.
The 2021 shooting of thirteen-year-old Adam Toledo [14] by a Chicago Police Department officer became one of the most analyzed use-of-force incidents in the city’s recent history. Body-camera footage showed that Toledo tossed a handgun behind a fence and turned toward Officer Eric Stillman with his empty hands raised less than a second before Stillman shot him. Whether that split-second sequence rendered the shooting an unreasonable seizure under the Fourth Amendment is contestable yet the question was never adjudicated. The federal civil lawsuit that followed resulted in a settlement that was paid by the City of Chicago, not by the officer personally. The case represented the central dysfunction: the financial consequence fell on the municipality, while the officer, shielded by qualified immunity and departmental procedures, faced no personal civil liability. The constitutional question of whether the shooting violated Toledo’s Fourth Amendment rights was never adjudicated in civil court. The city settled, so the question was buried, and no precedent was created that might constrain future conduct in similar situations.
The Scale of Chicago’s Misconduct Problem
Toledo’s case is not an aberration, but a representative of a systemic pattern. 272 officers had cost Chicago taxpayers roughly $295 million since 2019, which is nearly 60 percent of the city's total police-misconduct payouts over that period. [15] By April 2026, the city had already spent at least $175.6 million in that year alone to resolve misconduct lawsuits. [16] These amounts do not account for cases that were dismissed on qualified immunity grounds before settling, meaning the documented financial toll likely understates the true scope of constitutional violations occurring within the department.
The case of Carl Reed [17] further illustrates the repeat offender problem at the core of Chicago’s crisis. Carl Reed spent nearly nineteen years in prison after he was wrongfully convicted of murder, with the city of Chicago backing a $9.5 million settlement. [18] Reed suffers from severe cognitive difficulties, which the detectives exploited. According to his lawsuit, police obtained his confession after shackling him to a wall on a bare metal bench for fifty-five hours, physically beating him, denying him his diabetes medication, and psychologically torturing him until he signed a prewritten confession that he could not even read. Reed’s case exemplifies how individual officers with documented histories of misconduct continue to operate without consequence because qualified immunity forecloses the civil accountability mechanisms that might otherwise remove or discipline them. When constitutional violations are never formally adjudicated, misconduct records remain incomplete, disciplinary processes are undermined, and the legal system provides no external pressure for institutional correction. The two cases of Toledo and Reed illustrate the distinct but related failures of the current system. The shooting of Adam Toledo demonstrates how qualified immunity displaces financial consequence onto the municipality while leaving the constitutional question unanswered. The second, the wrongful conviction of Carl Reed demonstrates how the repeat offender problem compounds when officers with documented misconduct histories face no individual accountability.
One structural barrier compounding Chicago’s accountability problem is the sworn affidavit requirement, [19] which in practice raises the procedural threshold for misconduct complaints and discourages civilian reporting. When combined with qualified immunity’s doctrinal barriers at the judicial level, this creates a layered system of protection, one that operates at both the administrative and legal stages to prevent officer conduct from being formally examined. Misconduct that is never reported cannot be investigated, and misconduct that is investigated but settled without adjudication never produces the legal precedent necessary to clearly establish rights. Without clearly established rights, qualified immunity is granted, and the cycle begins again.
The relationship between qualified immunity and repeated misconduct is not incidental but structural. Research on police misconduct consistently identifies a small percentage of officers responsible for a disproportionate share of complaints, uses of force, and civil suits. In Chicago, data from the Civilian Office of Police Accountability and prior reporting from the city’s inspector general have identified officers with double-digit complaint histories who remain on active duty. Qualified immunity contributes to this problem in two distinct ways. [20]
First, because courts granted immunity without adjudicating the constitutional question after Pearson, officers with repeated violations never accumulated a formal legal record of having violated constitutional rights. Without that record, the “clearly established” threshold can never be met in future cases involving the same officer, even when the pattern of conduct is obvious. Second, the absence of personal financial liability removes one of the few individual-level deterrents that civil litigation might otherwise provide. Officers who know that the city will absorb any settlement cost, and that courts are likely to grant immunity before reaching the constitutional question, have no legally structured incentive to correct their conduct.
The most legally grounded reform available within the existing doctrinal framework is available under Saucier, where courts are required to first determine whether the officer’s conduct constituted a constitutional violation, and only then assess whether that right was clearly established at the time. Pearson made this sequencing discretionary, and courts in high-caseload jurisdictions have, for the most part, abandoned it in favor of the more efficient route of granting immunity without reaching the constitutional question.
Restoring mandatory sequencing would not abolish qualified immunity or expose officers to unlimited liability. It would, however, ensure that constitutional questions are resolved and that those resolutions accumulate into a body of precedent that progressively defines the boundaries of lawful conduct. Over time, this would narrow the category of conduct for which immunity can plausibly be claimed, creating legal clarity that the current system deliberately avoids.
In high-misconduct jurisdictions like Chicago, the case for restoration is especially strong. The city’s settlement data demonstrates that constitutional violations are occurring at scale, yet because courts routinely bypass the constitutional question, that scale is never reflected in legal precedent. Restoring Saucier’s sequencing would not immediately reduce misconduct, but it would begin to close the doctrinal gap that allows repeat violations to persist without legal consequence. Combined with stronger Monell claims linking departmental patterns to municipal policy, mandatory sequencing could reintroduce the accountability pressure that Pearson effectively removed.
Chicago’s crisis is not simply a failure of policing, but one of legal doctrine. Qualified immunity, as it is currently structured, does not just fail to deter misconduct but actively prevents the development of the legal standards that would make deterrence possible. By allowing courts to skip the constitutional question, Pearson v. Callahan created a system in which violations can accumulate, cities pay, officers continue, and the law remains silent. Restoring the mandatory two-step analysis of Saucier v. Katz would not solve the problem overnight, but it would restore the mechanism by which constitutional law is built, violation by violation, case by case, until the doctrine reflects the reality of what is happening in Chicago.
[1] Heather Cherone, "4 Months Into the Year, Chicago Has Spent at Least $175.6M to Resolve Police Misconduct Lawsuits," WTTW News, April 15, 2026, https://news.wttw.com/2026/04/15/4-months-year-chicago-has-spent-least-1756m-resolve-police-misconduct-lawsuits.
[2] Pierson v. Ray, 386 U.S. 547 (1967)
[3] Pearson v. Callahan, 555 U.S. 223 (2009)
[4] Saucier v. Katz, 533 U.S. 194 (2001).
[5] Qualified Immunity, National Conference of State Legislatures, 2021,https://www.ncsl.org/civil-and-criminal-justice/qualified-immunity.
[6] Harlow v. Fitzgerald, 457 U.S. 800, 818 (1982).
[7] Pierson, 386 U.S. at 557.
[8] Pearson, 555 U.S. at 236.
[9] Saucier, 533 U.S. at 201.
[10] Joanna C. Schwartz, "How Qualified Immunity Fails," 127 Yale Law Journal 2 (2017).
[11] Taylor v. Riojas, 592 U.S. 7 (2020) (per curiam).
[12] Taylor, 592 U.S. at 8–9
[13] Monell v. Department of Social Services of the City of New York, 436 U.S. 658 (1978).
[14] Heather Cherone, "Adam Toledo's Family Sues the City Again Over 13-Year-Old's Death—This Time in Federal Court," WTTW News, May 28, 2026,https://news.wttw.com/2026/05/28/adam-toledo-s-family-sues-city-again-over-13-year-old-s-death-time-federal-court.
[15] "COPA Publishes Video Showing Fatal Police Shooting of 13-Year-Old Adam Toledo," WTTW News, April 15,2021, https://news.wttw.com/2021/04/15/copa-publishes-video-showing-fatal-police-shooting-13-year-old-adam-toledo
[16] Heather Cherone, "Repeated Police Misconduct by 272 Officers Has Cost Chicago Taxpayers $295M Since 2019," WTTW News, September 23, 2025,https://news.wttw.com/2025/09/23/repeated-police-misconduct-272-officers-has-cost-chicago-taxpayers-295m-2019-analysis
[17] Cherone, "4 Months Into the Year."
[18] Jason Meisner, "City Council Panel to Weigh $9.5 Million Settlement with Man Who Spent 19 Years in Prison for Wrongful Conviction," CBS Chicago, April 13, 2026, https://www.cbsnews.com/chicago/news/carl-reed-wrongful-conviction-settlment-murder-chicago-city-council-finance-committee/.
[19] Tara Molina, "Feds Say Sworn-Affidavit Rule Undercuts CPD Misconduct Probes," CBS Chicago, January 13, 2017, https://www.cbsnews.com/chicago/news/feds-say-sworn-affidavit-rule-undercuts-cpd-misconduct-probes/
[20] Heather Cherone, "Inspector General Launches New Dashboard to Identify 'Hot Spots' of Police Misconduct," WTTW News, January 14, 2026,https://news.wttw.com/2026/01/14/chicago-inspector-general-launches-new-dashboard-identify-hot-spots-misconduct
