S3 E06: Brotherly Love

In 1998, Frank Calabrese Jr. makes the most dangerous decision of his life: he writes a letter to the FBI offering to turn against his own father—one of the most feared mob enforcers in Chicago history. What follows is one of the most audacious undercover operations in the history of organized crime. In this episode, we go inside the moment that changed everything for the Calabrese family and the Chicago Outfit. After being transferred to the same prison as his father, Junior realizes the only way to escape is to cooperate. He offers to wear a wire inside federal prison, hoping to capture Frank Calabrese Sr. incriminating himself in decades of unsolved mob murders. Told through secret recordings, FBI testimony, and Junior’s own words, this is the story of how one son risked his life to dismantle the family empire he was born into. It’s also the origin of the evidence that would form the heart of the Family Secrets case—the case that brought down the Outfit. Binge the entire season of Killing Kurt—along with other gripping Entropy Media shows—completely ad-free by subscribing to Entropy Unlimited on Apple Podcasts. Unlock exclusive access to bonus content and enjoy your favorite stories without interruptions. Click ⁠HERE ⁠to learn more! Learn more about your ad choices. Visit podcastchoices.com/adchoices