Synopsis
When Corruption Was King: How I Helped the Mob Rule Chicago, Then Brought the Outfit Down by Robert Cooley, co-authored with journalist Hillel Levin, is a gripping true-crime memoir that chronicles Cooley’s transformation from a corrupt Chicago mob lawyer to a pivotal FBI informant who helped dismantle the Chicago Outfit, one of the most powerful Mafia families in American history. Born in 1943 to an Irish-American family in Chicago’s Greater Grand Crossing, Cooley grew up steeped in the city’s gritty culture, with a father and grandfathers who were Chicago police officers, two of whom died in the line of duty. Despite this legacy, Cooley’s turbulent youth and brief stint as a cop exposed him to the city’s underbelly, leading him to law school and, ultimately, into the heart of Chicago’s organized crime network. As the Outfit’s go-to “mechanic” during the 1970s and 1980s, Cooley became a master fixer, bribing judges, court clerks, juries, and police to secure acquittals for mobsters, including hitmen like Harry “The Hook” Aleman, gambling czar Marco D’Amico, and political operative Pat Marcy, a protégé of Al Capone. Paid handsomely, Cooley lived a fast life, indulging in Chicago’s vices—gambling, nightlife, and mob protection—while rubbing shoulders with notorious figures like Tony Spilotro and dining at “last suppers” with associates before their gangland executions. His insider status gave him unparalleled access to the Outfit’s stranglehold on Chicago’s government, courts, and police, a system so corrupt that, as Cooley reveals, acquittals for murder were available for the right price.
The memoir takes a dramatic turn in 1986 when Cooley, driven by a crisis of conscience he attributes to the influence of his late father’s integrity, walked into the U.S. Organized Crime Strike Force office and offered to wear a wire against the very mobsters who trusted him. This decision, made without a pending conviction or immediate threat, launched Operation Gambat (short for “Gambling Attorney”), a sweeping federal probe that exposed the Outfit’s deep ties to Chicago’s political and judicial systems. Cooley’s tapes and testimony became the cornerstone of nine landmark trials in the 1990s, leading to the convictions of 24 individuals, including mobsters, politicians, police, and judges. The book vividly recounts the tension of Cooley’s undercover work, detailing sweat-inducing stings and meetings with dangerous figures, all while living with a million-dollar contract on his head. Cooley doesn’t shy away from his own moral failings, candidly describing his descent into corruption despite his family’s values, though some readers find his insistence on pure motives—claiming he acted out of justice rather than self-preservation—somewhat self-serving and hard to fully credit. Critics note the prose, while engaging, is functional rather than lyrical, but the narrative’s strength lies in its raw honesty and insider perspective, offering a rare glimpse into mob rituals, like the somber “last suppers,” and the mechanics of Chicago’s corrupt machine.
Cooley’s story also explores the personal toll of his double life. After turning informant, he lived in constant danger, receiving only grudging federal assistance to maintain a new identity outside the Witness Protection Program, forcing him to move frequently across the U.S. The memoir sheds light on overlooked aspects of organized crime, particularly the role of political corruption in sustaining the Outfit’s power, with figures like Pat Marcy and First Ward bosses orchestrating a system that controlled everything from courtrooms to City Hall. Cooley’s accounts, while occasionally unverifiable, paint a vivid picture of Chicago’s underworld from the 1970s to the 1990s, a period when the city’s reputation for corruption rivaled its Prohibition-era infamy under Capone. Reviewers praise the book as a thrilling counterpart to works like Gus Russo’s The Windy City Outfit, with its detailed analysis of how the mob infiltrated Chicago’s institutions. Some Chicagoans express shame at the extent of the corruption Cooley exposes, noting its persistence into modern times, while others commend his courage, comparing his story to films like Serpico or Prince of the City. Despite criticisms of self-aggrandizement, When Corruption Was King remains a compelling, eye-opening account of one man’s journey from enabling the mob’s dominance to risking everything to bring it down, offering a stark portrait of a city where justice was often for sale.