12: The Boss

Howie Winter was the original boss of the Winter Hill gang. He saved Whitey Bulger's life, only to be betrayed by the ultimate dirty rat. But perhaps the most unique part of Winter's life was not his mobster past, but his marriage. This episode of Dirty Rats is a love story between the infamous mob boss and his devoted wife, Ellen Brogna.

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First, Huff realized he was being followed whenever he was in Boston. But that was only the beginning. Over the next few decades, Mike Huff would uncover one of the biggest FBI scandals in modern history.

Mike Huff was a 25-year-old cop from Tulsa, Oklahoma. His career had barely begun when he embarked on a case that would change the trajectory of his entire life. It all started with the brutal murder of a millionaire tech-company CEO in the parking lot of the most exclusive golf club in the state.

But John underestimated just how dangerous his new associates were. And before he knew it, Callahan was over his head. Whitey decided that he couldn't trust the Callahan. After all, he was a civilian. There was no way to be certain that he'd stand up. So the mobsters, under direction from Whitey, found a solution to their dilemma. It involved Callahan, the Cubans and the trunk of a Cadillac. 

In this episode, you will hear from John Callahan's widow Mary. It has been 37 years since she found out her husband was murdered. But Mary shares much more than just her recollection of John’s death. She shares the story of their lives. Mrs. Callahan reminisces about her memories with the man she loved.

In this podcast you'll hear an interview with Joe Malone. He was the reform candidate elected treasurer of Massachusetts in 1990, just as the stories of Whitey and Billy Bulger's sordid deeds were beginning to become public. Malone talks about the corruption of the Boston Globe, how Zip Connolly tried to get him to stop criticizing Billy Bulger, and when Whitey  "won" Mass Millions during Malone's first year in office.

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As one of the lead prosecutors in Whitey Bulger's 2013 trial, Brian Kelly gained firsthand insight into the mind of one of America's most wanted criminals. Kelly faced one of the most notorious serial killers in the courtroom, confronting him with his own past so that a jury could determine his future. Dirty Rats producer Grace Curley discusses Whitey's trial and other prolific cases Kelly has had a hand in prosecuting in this bonus episode.

It was June 19, 2003 and Billy Bulger was under oath. The powerful politician would finally have to answer questions on live TV from appalled congressmen about his alleged involvement in the bloodstained career of his fugitive gangster brother Whitey as well as about two generations of corruption in the Boston office of the FBI.Bulger's fellow Democrats from Massachusetts would be asking him even tougher questions than the Republicans on the House committee. For once in his life Billy Bulger, the former President of the Massachusetts Senate, was in the hot seat. And the entire nation was waiting to hear what Whitey Bulger’s brother had to say.If you like this podcast, please consider becoming a supporter on Patreon: https://www.patreon.com/join/dirtyratspod