Prosecuting Chicago’s Gangs

July 11, 2023

The non-prosecution of street crime has allowed gangs to believe themselves beyond the law

When Cook County State’s Attorney Bernard Carey was approached with the grim news venality and corruption had adulterated Cook County courts, one of his first acts was to speak with Thomas P. Sullivan, who was the then-United States Attorney for the Northern District of Illinois. Recalling the exchange with Carey, Sullivan revealed decades later Carey’s appeal for assistance to contend with the fetid pool of corruption sweeping through the court system was based on Carey’s realization his office was insufficiently staffed and funded to shoulder a probe of such scale.  

A notable prosecutor, Sullivan applied his calm, methodical legal mind to what would become known as Operation Greylord. Following President Jimmy Carter’s defeat in the 1980 election, Sullivan was replaced by Dan Webb, who, with a social scientist’s detachment and dispassion, embarked on a complex, lengthy, and challenging investigation. Over the next four years, Webb and FBI agents uncovered a preponderance of evidence demonstrating a massive case-fixing scheme involving judges, Cook County prosecutors, lawyers, court bailiffs, clerks, and a state lawmaker. Working undercover, federal agents posing as prosecutors, criminal defense attorneys, victims of crimes, and criminals, fabricated criminal cases to ensnare — amongst others — corrupt public officials and defense attorneys involved in bribery, kickbacks, and fraud.  

After leading the probe for four years, Webb departed the U.S. Attorney’s office and was replaced by Anton Valukas. Valukas pursued Greylord, which concluded in 1988, and by the time the final trial concluded in 1994, prosecutors had secured an astonishing 92 convictions or guilty pleas. Among those found guilty or entering guilty pleas were 17 judges.

At the time of Carey’s conversation with Sullivan which lit the fuse to prosecute wrongdoing in the courts, elected leaders in Chicago shared the same end-goals: The desire to prosecute criminal behavior. To carry out an investigation of this magnitude requires time and patience, and prosecutors had a specific obligation to see procedural justice applied and guilt determined upon the basis of sufficient evidence, rather than public opinion.

Today, however, a prevalent ideology — progressivism — dictates whether an individual is charged and placed on trial. A doctrine which demands why a crime was committed rather than who committed a crime, its practitioners have spent the last decade dialing back criminal prosecutions and framed the non-prosecution of crime as police tending to direct attention only to minorities. Though an utter falsehood, the results of non-prosecution have wrought disaster for Chicago, and nowhere have the city’s progressive leaders failed more significantly than in the prosecution of gang crime.

Decades ago, Chicago gangs were highly structured, ordered formations, and their leaders masterfully carved out kingdoms through the strength of their swords in housing projects. Seats over which to rule their criminal fiefdoms, the horror stories of gangs terrorizing law-abiding tenants and turning playgrounds into battlefields were legion. Following the razing of public housing and the prosecution of several powerful gang leaders, gangs were dislodged from their crusty dens and became splintered and scattered throughout communities across Chicago.

Forced from their perch of public housing, gangs mounted an aggressive effort to secure neighborhood hegemony through intimidation and violence. Moored to the same tactics which conferred gangs the means to annex public housing, the rise of criminal gangs in residential neighborhoods turned the ebb and flow of everyday life in some quarters of Chicago into a steady flow of drug sales and violence.

Intoxicated by battle-lust, gangs turned life in some neighborhoods upside down: The recruitment of children into turf wars flourished, as did the assassinations of rivals, forays on drug houses, and the ambush of nemeses in the drug trade. More troubling is the smallest affront can incite a savage and protracted gang war. Though gang violence traditionally revolved around control over territory and drug dealing, personal feuds are today fomented by rival gang members inserting themselves into an adversary’s romantic relationship or over a social media grievance. Rap artists becoming deeply interwoven in Chicago’s gang culture have also led to bloody acts of violence.

While gang activity long involved the gradual wresting of control of territory from competing gangs to expand drug trafficking, criminal gangs have only recently become more sophisticated in their illicit endeavors. Looking further afield, gang lucre has been earned through elaborate check washing schemes, Cash App fraud, counterfeiting, identity theft, and deceptively obtaining Paycheck Protection Program (PPP) loans.

Despite gangs establishing a well-deserved reputation as some of the most depraved killers on Chicago’s streets, the prosecution of gang members has waned in the past decade. In the event the Cook County State’s Attorney’s Office (CCSAO) does deign to prosecute gun offenses, Chicago police say Kim Foxx often spares gun offenders lengthy prison terms or prefers probation for criminal offenders. Police speculate the explanation for leniency or non-prosecution is not found in the law, but entirely in politics. Progressive doctrine sweeping through the CCSAO, CPD gang officers say, demands sympathy be extended to violent gang members. This reality, coupled with the anti-police movement declaring all policing strategies racist and the elimination of proactive policing, has left gang members quite literally thinking themselves to be a protected class which enjoys an immunity from the law. The mollycoddling of gang members and limits placed on vigilant policing has led to an increase in gun violence on Chicago’s streets.

With more than 80 percent of gun murders attributed to gangs — incidents which often injure or claim the lives of innocents — Chicago has reached a juncture at which federal intervention is critical to prosecute gun offenses. Given the sheer brutality of the crimes committed by gangs and the passive inertia of Kim Foxx’s office, the wide range of federal law-enforcement agencies — DEA, ATF, FBI — within the reach of the U.S. Attorney’s Office is the only recourse to slow the carnage.

Federal involvement in local matters is not irregular, and recent developments have proven effective. In two instances in the past five years, federal authorities have stepped in to prosecute gun crime with great success. In 2018, the Department of Justice (DOJ) indicted four members of the Chicago street gang faction, the Goonie Boss/Goonie Gang. Three of the defendants, Romeo Blackman, Terrance Smith, and Jolicious Turman, were convicted in July 2023 on a raft of charges, including racketeering conspiracy, multiple counts of violence in aid of racketeering, and liability for the murder of six men. Both Blackman and Smith are facing mandatory life sentences in federal prison; Turman is facing 20 years behind bars. A fourth defendant, Nathaniel McElroy, entered a guilty plea prior to trial and is awaiting sentencing.

Two years later, in July 2020, marked the debut of Operation Legend in Chicago. Part of a nationwide federal crackdown on gun crime in urban areas, the Trump White House inaugurated Operation Legend in response to the shooting death of four-year-old LeGend Taliferro, who was shot and killed while sleeping in his home in Kansas City. In the first two weeks of the campaign, federal agents working with CPD netted 21 arrests. Of the 21 originally taken into custody in the first two weeks of Operation Legend, 13 men pleaded guilty. In total, nine were sentenced, with eight eventually receiving jail terms averaging about three and a half years. 

When Bernard Carey approached Thomas Sullivan to apprise him of corruption at the very heart of the Cook County courts, both Carey and Sullivan understood to ignore the malfeasance would be a terrible disservice to precious justice. Carey’s and Sullivan’s courage to pursue a matter of such consequence signaled both men possessed political determination and a willingness to see past party affiliation to achieve justice.

Today, unfortunately, no elected leaders in Cook County own the political resolve to oppose gangs. Oddly, some aldermen have naively claimed gangs can somehow serve as our partners in peace. While an antiquated strategy of confronting gangs may be crippling CPD efforts to thwart gang violence, the single greatest obstacle to placing checks on gang-related crime is Kim Foxx. A renunciation of a social covenant to fight crime, Foxx’s refusal to vigorously pursue criminal gang members has left the responsibility to fight gangs to the Justice Department. With gangs responsible for committing an astonishing 80 percent of crime on Chicago’s streets, and the fact gangs have expanded their criminal endeavors into financial crimes, the DOJ should recognize an urgency and assume more criminal prosecutions in Chicago.

Gangs are not a normal enemy and the prosecution of gang crime requires a special effort and determination. In Chicago today, it is estimated over 100,000 members are affiliated with 55 known criminal gangs. Of the 55 documented gangs, some 700 factions exist, and within those 700 factions reside over 2,000 sets. Gangs place no value on human life, only life style, which is a paroxysm of fast cash, rabid murder, and terrorizing the law-abiding. Hardly a lifestyle which should engender any sympathy, gangs in Chicago are creating a crime wave which destroys communities, claims lives, and hurts minorities the most.

For all their self-proclaimed compassion, Chicago’s progressive lawmakers are, in important respects, doing significant harm to the City of Chicago by refusing to prosecute crime. Progressive lawmakers do not realize the damage they are doing. They should because human lives should take priority over political ideology. The problems of Chicago will only be solved when it is governed by leaders who value the lives and the property of law-abiding residents as do the law-abiding. Since Chicago's progressives are uninterested in confronting crime, the federal government should step in to reverse Chicago’s disastrous course.

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