The Chicago Cop Who Worked for Sam Giancana | Richard Cain

Richard Cain wore a badge, worked for the Chicago Outfit, and developed secrets that made him dangerous to both sides.

Retired Kansas City Intelligence Detective Gary Jenkins welcomes Michael Cain, Richard’s half-brother and author of The Tangled Web: The Life and Death of Richard Cain, Chicago Cop and Mafia Hit Man. Drawing on family letters, police records, court transcripts, and interviews, Michael traces Richard’s path from Chicago vice detective to a trusted associate of mob boss Sam Giancana.

Michael describes allegations of police payoffs, compromised investigations, a leaked jury list in Tony Accardo’s case, and a staged recovery of stolen pharmaceuticals. He also discusses Richard’s wiretapping work in Cuba, his years in Mexico, and the convictions that sent him to federal prison.

The conversation builds toward Michael’s account of Richard’s extraordinary plan to eliminate the Outfit’s leadership—and his murder at Rose’s Sandwich Shop before that plan could unfold. It’s a family perspective on one of Chicago’s most complicated underworld figures, with Gary bringing a detective’s eye to the difference between Richard’s stories and the evidence he left behind.

In this episode:

• Richard Cain’s relationship with Sam Giancana.

• Cash envelopes and corruption inside the Chicago police.

• His rise to lead Cook County’s Special Investigations Unit.

• Tony Accardo’s jury list and the FBI’s response.

• Criminal cases, prison, and Richard’s return to Mexico.

• Michael’s account of a planned takeover of the Chicago Outfit.

• The fatal ambush at Rose’s Sandwich Shop.