Chicago lawyer Bob Cooley was enmeshed in the mob, until one day in 1986, his life sharply switched gears. On a whim, he walked into a federal prosecutor’s office to report on one of the nation’s most dangerous crime syndicates. In the 1980s, Chicago was one of America’s most corrupt cities, loaded with bribe-accepting elected officials, and Cooley claimed he had all the intel they could possibly need to take down the mob. Pulitzer Prize-winning journalist Jake Halpern narrates this saga in “Deep Cover: Mob Land” and allows Cooley and those involved in the case to share the story in their own words.
Now in its second season, stream the podcast from the first episode to hear the story unfold in chronological order each season. The average length of episodes is 45 minutes long.
Cooley worked for the mafia and bribed government officials to grant case decisions in his clients’ favor. Cooley did not look like Chicago’s typical suit-and-tie lawyers from the city. Instead, he wore tight turtlenecks, a gold chain, and slicked-back hair, which perhaps added to his causal brand of being a “fixer.” If cases did not go well, Cooley was known for fixing situations with a rolodex of contacts at the ready.
The federal prosecutor questioned Cooley’s motivations for forking over all this info and wanting nothing in return. But in actuality, he thought he was protecting himself. He first informed the feds about gambling that funded illegal activity and corruption in the city, opening the confession floodgates. Cooley volunteered to become an informant “to clean up the system.” Cooley was a gambler and enjoyed sports betting. At the time he walked into the federal prosecutor’s office, Cooley had racked up significant debts. He saw how the mafia recruited new members and the serious consequences folks suffered when struggling to pay back gambling debts, essentially turning into the mob’s slaves.
From episode one, listeners hear why the FBI agents working the case were suspicious of Cooley’s motives. By the second episode, we learn that teamster William Logan was shot in 1972, and it’s believed to be a mob hit. In 1977, mob hitman Harry Aleman took the stand for Logan’s murder trial, and Cooley “handles” it. Episode four goes back to Cooley’s childhood in 1942. In 1973, more attempts are made to clean the court, and by 1986, Cooley represents a client who attacked a police officer.
In 1988, Cooley continued working undercover and wore a wire, leading the FBI to three targets. Another critical target is revealed by the eighth episode, and Cooley’s cover is nearly blown. By 1989, Cooley’s work affects an old friend, and he flees Chicago. Two trials begin in 1997 with Cooley’s wiretap evidence at the forefront, and a mafia kingpin is brought down. Cooley shares how this course of events impacted his life forever.
Season one of “Deep Cover” covered The Drug Wars, recounting the time an FBI agent went undercover with a biker gang. Following clues, witnessing crimes firsthand, and obtaining enough information that unintentionally brought the US to invade a foreign country.
Tune into new episodes of Pushkin Industries’ “Deep Cover: Mob Land” released on Mondays. Pushkin Industries’ subscribers can now stream the entire season.