Deep Cover: Mob Land

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Deep Cover is a show about people who lead double lives, how far they’re willing to go in pursuit of a greater cause, and how sometimes, seemingly small decisions can change the course of history. Pulitzer Prize-winning journalist Jake Halpern reveals webs of deception and dark underworlds, through interviews with federal agents and convicted criminals.

Season two, Mob Land, is about a high-rolling lawyer who joins forces with the feds to try to bring down one of the most powerful criminal syndicates in the country.

And listen back to season one, The Drug Wars, which tells the story of an FBI agent who goes undercover with a biker gang, and follows a trail of clues that eventually leads to the US invasion of a foreign country.

Most Recent Episode

Camouflage Bias: Part 2

2022. After Ronnie Carrasquillo exhausts his appeals, he faces the Illinois Prisoner Review Board. But it seems each time Ronnie comes up for parole, he can’t escape the notoriety of…

Camouflage Bias: Part 1

1978. A few months after the Aleman trial wraps up, the presiding judge, Frank Wilson, sentences a young man named Ronnie Carrasquillo to 200-600 years in prison for murder. But…

Episode 10: The Witness

September 1997. Bob’s wiretap evidence culminates in two major trials and the downfall of a mafia kingpin. But was it all worth it for Bob?

Episode 9: The Vanishing

November 1989. Bob’s undercover work has some serious consequences for an old friend. His days as an operative end suddenly when he flees Chicago.

Episode 8: The Big Fish

April 1989. Bob goes after his most important target: Pat Marcy. But as he works his way up the criminal ladder, he risks being discovered.

Episode 7: The Philosopher King ft. Michael Imperioli

December 1988. Bob wires up. He and the FBI set their sights on three targets: a mobbed-up car salesman, a bookie, and… a poet. Voice acting in this episode by…

Episode 6: The Breaking Point

February 1986. Bob Cooley represents a bodybuilder who brutally assaulted a female police officer. Then Bob makes a decision that will change his life forever.

Episode 5: The Babe in the Woods

July 1973. Who can stem the tide of corruption in Chicago? In this episode: two attempts to clean up the courts. And where they fell short.

Episode 4: The Favorite Son

July 1942. How did Bob Cooley, an Irish ex-cop from a family of cops and lawyers, become Bob Cooley, criminal defense lawyer and fixer for the Chicago Outfit?

Episode 3: The Fix

May 1977. After a witness decides to speak out, a hitman named Harry Aleman stands trial for the murder of William Logan. Bob Cooley is asked to “handle it.” The…

Episode 2: The Murder

September 1972. A teamster named William Logan is gunned down outside his home, in what’s widely thought to be a mob hit. The Logan family is determined to get justice,…

Episode 1: The Walk-In

March 1986. A high-rolling lawyer named Bob Cooley walks into a federal prosecutor’s office and says that he has information that could bring down the mob.

Deep Cover Season Two Trailer

Who was Bob Cooley? Deep Cover Season Two launches on January 24th. Listen to the whole season early and ad-free by subscribing to Pushkin+.

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