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.

The St. Patrick’s Day breakfast in South Boston was Billy Bulger’s annual tribute to himself. Whether it was presidents, governors or corrupt FBI agents, attendance was mandatory. But despite the music and the corned beef and cabbage, there was always an unmentioned presence in the hall– Whitey.

Det. Mike Huff was quickly realizing that the murder of Roger Wheeler was unlike any case he had ever covered in Tulsa. 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.

John Callahan was getting closer to the gangsters from Boston. He was constantly searching for excitement in his life and these were the kind of guys he had always seen in movies. 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.

John Callahan had a loving wife and two children. He was a successful businessman who worked everywhere from Ernst & Young to Arthur Andersen. And yet, even as his family grew and his career excelled, John was restless. And that restlessness would cost him dearly.

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.

Why did Billy Bulger suspect that his serial-killing fugitive brother would be murdered if he were captured by the FBI? In this week’s podcast, the former Senate president presciently predicts the future at a Congressional hearing — more than 15 years before Whitey Bulger would be murdered at a federal prison in West Virginia.

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.