Dirty Rats

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

The first of those victims was Arthur "Bucky" Barrett. His murder would go down as one of the gang's most cruel and unnecessary killings. Even Stevie "the Rifleman" Flemmi later claimed he was shocked by Whitey's brutality.If you like this podcast, please consider becoming a supporter on Patreon: https://www.patreon.com/join/dirtyratspod

A native of South Boston like the Bulger brothers, he handled their dirty work for a quarter century, becoming a multi-millionaire on a policeman's salary. As a decorated G-man, he made training videos for the FBI academy, which you will hear, instructing young agents how to handle organized-crime informants. At the same time, though, he was tipping his underworld paymaster Whitey to informants so that they could be murdered."Never try to out-gangster a gangster," Connolly said, but now he's serving a life sentence in a Florida state prison for a gangland hit he orchestrated in Miami.If you like this podcast, please consider becoming a supporter on Patreon: https://www.patreon.com/join/dirtyratspod

Deb Davis was a beautiful blonde who dreamed of becoming a model, and of escaping from the clutches of her boyfriend, who last year admitted in federal court to taking part, in one way or another, to more than 60 murders.But Stevie, 23 years her senior, was insanely jealous, and Whitey didn't much like women, period. So Deb Davis had to die, in the most grisly fashion imaginable.Davis was strangled to death in Stevie's home, which was a few feet away from Billy Bulger's house in Southie. And although both Whitey Bulger and Flemmi were serial killers, each blamed the other for the murder of Deb Davis at the age of 26, after which she was buried in a shallow grave on a riverbank, not to be found for 19 years.If you like this podcast, please consider becoming a supporter on Patreon: https://www.patreon.com/join/dirtyratspod

Whitey and Billy Bulger terrorized and corrupted Boston for more than 30 years -- Whitey as a serial-killing, cocaine-dealing mob boss on the FBI's Most Wanted List, and his younger brother Billy as the president of the Massachusetts state senate, the most powerful politician in the state.Each one's sinister power reinforced the other's -- as you will hear a former mayor of Boston say of Billy, "If my brother threatened to kill you, you'd be nothing but nice to me."This podcast is the introduction to the brothers Bulger, one of whom murdered dozens of people, including young women, and the other of whom remained one step ahead of the life as he intimidated police, politicians and judges for decades.Whitey is now dead -- beaten to death by rival gangsters in a federal prison in West Virginia, while Billy continues to collect a tax-free state pension of more than $200,000 a year.If you like this podcast, please consider becoming a supporter on Patreon: https://www.patreon.com/join/dirtyratspod