Deep Cover: The Family Man

Deep Cover: The Family Man

Author: Pushkin Industries May 11, 2026 Duration: 4:00

Every family has its secrets. On the new season of Deep Cover, Jake Halpern tells the story of the crimes one man committed in the name of fatherhood–and what happened when his daughters discovered he was living a double life. 

New episodes drop May 18. Subscribe to Pushkin+ to binge the entire season, ad-free. Find Pushkin+ on the Deep Cover show page in Apple Podcasts or at Pushkin.fm.

See omnystudio.com/listener for privacy information.


There's a hidden world that exists just beneath the surface of everyday life, and Deep Cover pulls back the curtain. This Pushkin Industries production, rooted in history and true crime, isn't about casual secrets; it's an excavation of the elaborate double lives people construct, often at tremendous cost. Pulitzer Prize-winning journalist Jake Halpern guides you through these labyrinths, weaving together testimonies from the federal agents who pursue these stories and the convicted criminals who lived them. The result is a gripping narrative podcast that feels less like a lecture and more like stepping into a shadowy, parallel reality. One season might plunge you into a sprawling undercover operation, while another focuses on a devastating personal betrayal. For instance, in "Deep Cover Presents: Snowball," a special limited series from the team behind Unravel Podcast at the Australian Broadcasting Corporation, host Ollie Wards unpacks how his own family lost everything after encountering a charming con artist from California. Each episode is built on firsthand accounts, revealing the meticulous planning, the psychological toll, and the inevitable moment when a fabricated identity collapses. You'll hear the tension in a voice, the pause before a difficult admission, and the chilling details that only someone who was there can provide. It's a deep, often unsettling look at the lengths people will go to become someone else, and the tangled webs they leave behind for others to unravel.
Author: Language: en-us Episodes: 75

Deep Cover
Podcast Episodes
Camouflage Bias: Part 1 [not-audio_url] [/not-audio_url]

Duration: 24:04
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 Ronnie’s lawyer claims there's much more t…
Episode 10: The Witness [not-audio_url] [/not-audio_url]

Duration: 49:25
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? Tickets to my upcoming digital experience on true crime storytelling are on sale…
Episode 9: The Vanishing [not-audio_url] [/not-audio_url]

Duration: 38:10
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.Tickets to my upcoming digital experience on true crime storytelling are o…
Episode 8: The Big Fish [not-audio_url] [/not-audio_url]

Duration: 35:07
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.Tickets to my upcoming digital experience on true crime storytelling are on sale…
Episode 7: The Philosopher King ft. Michael Imperioli [not-audio_url] [/not-audio_url]

Duration: 37:34
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 Michael Imperioli. Learn more about your ad-choices at https…
Episode 6: The Breaking Point [not-audio_url] [/not-audio_url]

Duration: 32:06
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.This episode comes out for free on February 14th and is avail…
Episode 5: The Babe in the Woods [not-audio_url] [/not-audio_url]

Duration: 29:52
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. This episode comes out for free on February 7th and is available now for Pushkin…
Episode 4: The Favorite Son [not-audio_url] [/not-audio_url]

Duration: 38:48
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? This episode comes out for free on January 31st and is availa…
Episode 3: The Fix [not-audio_url] [/not-audio_url]

Duration: 45:56
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 case is make-or-break for Cooley’s career, and possibly hi…
Episode 2: The Murder [not-audio_url] [/not-audio_url]

Duration: 46:25
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, but it may not be so easy. Learn more about your ad…