How Chicago became an open-air insane asylum
For years, many North Side neighborhoods have lived under the comforting illusion that crime, disorder, and urban dysfunction were primarily someone else’s problem. Violence was something that happened on the South Side. Chaos was something that happened on the West Side. Public safety concerns were often dismissed as exaggerated talking points from conservatives, suburbanites, or those dreaded MAGA types. Then reality showed up and punched them in the head — literally.
According to reporting by Block Club Chicago, thousands of Lakeview residents are now demanding action after years of harassment, assaults, stalking, groping, threats, and violent behavior allegedly committed by two well-known repeat offenders, Leon Jackson and Willie Wright. Women have spent years warning one another on neighborhood Facebook groups about encounters with the two men. Residents report being followed, threatened, punched, groped, assaulted, and terrorized while simply trying to walk through their own neighborhoods.
These are not complaints coming from hard-core conservatives. This is Lakeview, precisely the kind of neighborhood that votes for progressive candidates by overwhelming margins. Yet even the most progressive citizen begins moving toward the law-and-order end of the political spectrum when they are repeatedly confronted by violent offenders who seem immune to consequences. As the old saying goes, "a conservative is often a liberal who has been mugged by reality." In this case, Lakeview residents have been mugged by reality and, allegedly, by two notorious repeat offenders.
The most remarkable aspect of the story is not that these incidents occurred. Every major city has troubled individuals and repeat offenders. The remarkable aspect is that, according to residents, this has been going on for years. Not months. Years. The article describes women sharing warnings about Willie Wright nearly a decade ago. Residents discussed being followed, harassed, grabbed, groped, and assaulted. One allegation even involved an attempt to drag a store employee into a bathroom. A judge eventually ordered Wright to stay out of portions of Andersonville, but residents say the problems simply migrated into neighboring communities.
Meanwhile, Leon Jackson allegedly became a familiar figure in Lakeview, with repeated accusations involving assaults, threats, and erratic behavior. Court records show numerous arrests involving battery, assault, aggravated battery, and aggravated assault. Yet despite years of arrests, court appearances, complaints, warnings, and community outrage, the problems persisted. The obvious question is, why is this happening?
The answer begins with what evolutionary psychologist Gad Saad calls “suicidal empathy,” which is the tendency of modern societies to place endless emphasis on understanding the circumstances, feelings, and struggles of offenders while paying comparatively little attention to the rights and safety of innocent citizens. Unfortunately, mental illness is real. Addiction is real. Homelessness is real. However, compassion divorced from reality is not compassion at all; it is negligence. When residents are repeatedly assaulted, threatened, harassed, and terrorized by the same individuals year after year, the primary moral obligation of government is not to endlessly psychoanalyze the offenders or search for new excuses for their behavior. The primary obligation is to protect innocent people.
Unfortunately, modern progressive governance often reverses those priorities. The result is a system in which citizens are expected to absorb an ever-growing burden of risk while officials endlessly debate the needs and rights of those who repeatedly victimize them.
The second problem is Chicago’s revolving-door criminal justice system. One of the most revealing observations in the Block Club article came from Alderman Bennett Lawson, who noted cases involving these individuals often feature different assistant state’s attorneys, different arresting officers, different victims, and different circumstances every time they enter the system. In other words, there is very little continuity. The criminal justice system evaluates each incident as a separate event rather than recognizing an obvious and longstanding pattern of behavior. Imagine a customer walking into the same store every week for 10 years and smashing a display case. If every incident were handled by a different manager who knew nothing about the customer’s history, the problem would never truly be addressed. Yet that appears to be precisely how Chicago frequently handles repeat violent offenders.
The criminal justice system has become a revolving door. Offenders cycle through arrests, hearings, short periods of detention, release, and then re-arrest. Residents become increasingly frustrated, police become increasingly demoralized, and public confidence in government continues to erode. Then, officials act surprised when trust in public institutions keeps falling.
The third problem is one politicians discuss constantly but rarely address honestly: severe mental illness. Mayor Brandon Johnson talks frequently about mental health clinics and mental health services (perhaps because he could benefit from such services). Those initiatives may have value, but they do not address the reality highlighted by the Lakeview situation. Some individuals are not merely struggling with mental illness; some are dangerously, chronically, and violently mentally ill. The hard truth is there are people who, at least given the current state of psychiatric treatment, cannot safely function in society. They repeatedly victimize others, repeatedly refuse treatment, repeatedly violate the law, and repeatedly cycle through hospitals, shelters, jails, courtrooms, and back onto the streets. The victims change, but the behavior does not.
For much of the 20th century, society dealt with this reality through long-term institutionalization. Many of those institutions were imperfect. Some deserved reform. Instead, we largely dismantled the system altogether. A combination of budget cuts, court rulings, ideological activism, and cultural influences — including the enduring impact of Ken Kesey’s One Flew Over the Cuckoo’s Nest — created a powerful movement toward deinstitutionalization. The theory was community-based care would replace institutional care. Unfortunately, the replacement never fully materialized. What we got instead was a system in which thousands of severely mentally ill individuals bounce endlessly between emergency rooms, shelters, jails, courtrooms, and sidewalks.
The consequences are visible throughout Chicago every day. We have effectively transformed portions of the city into an open-air insane asylum. That may sound harsh. It may sound politically incorrect. But what exactly are citizens supposed to conclude when the same violent individuals repeatedly assault people for years while government agencies debate jurisdictional boundaries, procedural limitations, staffing shortages, and legal technicalities? At some point, reality matters. The answer is not cruelty, nor is it abandoning people who suffer from severe mental illness. The answer is secure, humane, long-term facilities capable of treating and containing individuals who have demonstrated through repeated conduct they cannot safely function in society. Such facilities would protect the public while also protecting the individuals themselves, many of whom are incapable of making rational decisions about their own treatment and care.
Compassion and public safety are not mutually exclusive. In fact, the truly compassionate approach may be acknowledging that some people need far more supervision and structure than our current system is willing to provide.
Meaningful reform will also require leadership from the criminal justice system. Cook County State’s Attorney Eileen O’Neill Burke appears to grasp the seriousness of these issues better than many of her predecessors, and one useful reform would be the creation of a specialized unit dedicated to chronic repeat offenders whose histories involve violence, threats, harassment, and severe mental illness. Rather than assigning a different prosecutor every time one of these individuals appears in court, the same team could follow cases from beginning to end, track patterns of behavior, coordinate evidence, communicate with victims, and develop long-term strategies. Continuity matters. Institutional memory matters. Common sense matters. The current system often seems designed to ensure that nobody ever sees the entire picture, which makes meaningful intervention almost impossible.
Any serious solution will also require cooperation from Mayor Johnson, the courts, law enforcement, mental health providers, and the Cook County government. That last requirement may prove particularly challenging. The continued political dominance of Cook County Board President Boss Toni Preckwinkle remains one of the great mysteries of Chicago politics. After decades of observing the city’s Democratic machine in action, I remain astonished by her ability to survive politically despite chronic dysfunction throughout many county systems. Yet the growing outrage in Lakeview suggests something important may finally be changing.
When disorder reaches affluent neighborhoods, when progressive voters begin demanding accountability, when women can no longer walk safely to the grocery store, and when residents must organize petitions simply to get government officials to acknowledge an obvious problem, the political calculus begins to shift.
The citizens of Lakeview are discovering what residents in many other Chicago neighborhoods learned years ago: Public safety is not a partisan issue. It is the foundation upon which every other civic aspiration rests. Without safety, there is no vibrant neighborhood, no meaningful economic development, no quality of life, and no functioning civic culture. All the progressive slogans in the world become meaningless if ordinary people are afraid to walk down the street. Reality, unlike politicians, does not care about ideology. Sooner or later, it catches up with everyone, and for many residents of Chicago’s North Side, that moment appears to have arrived.
