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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Deb Davis
At age 17, Deb Davis made the mistake of hooking up with the bloodthirsty underworld partner of Whitey Bulger — Stevie “the Rifleman” Flemmi — and it would cost her her life.
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.Love the show? Become a supporter:
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Crooked Cop
John “Zip” Connolly was perhaps the most corrupt special agent in the tawdry history of the Federal Bureau of Investigation.
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.Love the show? Become a supporter:
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Blood Brothers
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.
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Special thanks to WGBH for audio content provided for this episode.
