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Episodes

May 02, 2022

Back in the Saddle Again - Jack "Red" Kelley's Armored Truck Heists

Jack “Red” Kelley loved taking armored trucks more than any other type of heist. We highlight the larger and more spectacular ones from 1965 to 1967. Plus, one of the men in Jack's crew calls FBI Director J Edgar Hoover from ...

Jack "Red" Kelley Carmello Merlino Richard Chicofsky Sonny Diaferio Armored Truck Heists

April 25, 2022

On The Waterfront - Part 2 - Punchy McLaughlin & Buddy McLean

The two leaders in Boston's 1960s Gang War were murdered within ten days of one another. We're taking you through the events that led up to their assassinations, the role played by Raymond Patriarca and the mafia, and why Edw...

Jimmy Flemmi Stevie Flemmi Raymond Patriarca Jerry Angiulo Buddy McLean Punchy McLaughlin

April 18, 2022

The Hit Parade of 1965 - The Slain & The Suspects

The gangland slayings continued in 1965. We're profiling the victims, and sharing own our theories, opinions (and snarky comments) about the FBI's investigations. Episode 25 Episode 17 Follow us on Twitter for sneak peeks of ...

Mafia Jimmy Flemmi Joseph Barboza Raymond Patriarca Jerry Angiulo Maurice "Pro" Lerner Jack "Red" Kelley Richard Chicofsky McLean McLaughlin Winter Hill

April 11, 2022

Frank Smith - Thief, Bomber, Pastor & Nazi Sympathizer

Frank Smith was more than just a thief. An associate of Raymond Patriarca who was labeled by the press as a "big wheel" and one of the best "dynamite men" in the business, Frank would later be famous for his Nazis in Maine sa...

Jimmy Flemmi Joseph Barboza Raymond Patriarca Henry Tameleo Sammy Linden Frank Smith Teddy Green Harvey Bistany

April 04, 2022

Edward "Teddy" Deegan - Part 3 - The Trial & The Aftermath

The final episode in our three-part series on the 1965 murder of Edward "Teddy" Deegan. If you haven't listened to the previous episodes, you can listen here: Episode 28 Episode 29 Episode 30 Follow us on Twitter for sneak pe...

FBI Informants Jimmy Flemmi Joseph Barboza H. Paul Rico Dennis Condon Boston Teddy Deegan Peter Limone

March 28, 2022

Edward "Teddy" Deegan - Part 2 - The Murder Investigation

Edward "Teddy" Deegan was murdered in Chelsea, Massachusetts on the evening of March 12, 1965. His murderers were never prosecuted. Instead, the FBI launched a decades-long coverup to protect his murderers, using one of them,...

FBI Informants Jimmy Flemmi Joseph Barboza H. Paul Rico Dennis Condon Boston Henry Tameleo Teddy Deegan Peter Limone

March 21, 2022

Edward "Teddy" Deegan - Part 1

Edward "Teddy" Deegan was murdered in Chelsea, Massachusetts on the evening of March 12, 1965. His murderers were never prosecuted. Instead, the FBI launched a decades-long coverup to protect his murderers, using one of them,...

FBI Informants Jimmy Flemmi Joseph Barboza H. Paul Rico Raymond Patriarca Jerry Angiulo Teddy Deegan

March 14, 2022

New York State of Mind - Raymond Patriarca

New England mafia boss Raymond Patriarca returns as he attempts to play power games with the New York mafia families, and closer to home in Massachusetts. Spoiler: it ends badly! Episode 21 Episode 22 Follow us on Twitter for...

Mafia Raymond Patriarca Jerry Angiulo Henry Tameleo

March 07, 2022

The Boys of Winter Hill

The Winter Hill gang was home to many of Boston's more infamous criminals, and serial killers, including the Flemmi brothers: Jimmy "The Bear" and his brother Stevie "The Rifleman", Howie Winter, "Cadillac" Frank Salemme, and...

Jimmy Flemmi Stevie Flemmi John Martorano Winter Hill Joe McDonald Howie Winter

February 28, 2022

The Defense Never Rests - Meet the Lawyers

Jack Kelley returns with his attorneys, John Fitzgerald and F Lee Bailey. Richie inserts himself into the Plymouth Mail Robbery investigation. The Feds wanted Richie to kidnap one of his fellow crew members OSS-style: using a...

Jack "Red" Kelley Billie Aggie Richard Chicofsky F. Lee Bailey John Fitzgerald Joseph Balliro Al Farese Ronald Chisholm

February 21, 2022

The Hit Parade 1964

18 men were murdered gangland-style in 1964 in mafia boss Raymond Patriarca's jurisdiction. Only one of those murders was ever prosecuted. The FBI had chosen a side in the McLean-McLaughlin feud, and used first murder of 1964...

FBI Informants Jimmy Flemmi Joseph Barboza H. Paul Rico John Kehoe McLaughlin Buddy McLean

February 14, 2022

Dying To Be Made - Joe Barboza - The Early Days

Self-proclaimed contract killer for the New England Mafia in the 1960s, Joe "The Animal" Barboza would go on to become the FBI's star witness in multiple murder cases. His perjury put numerous innocent people in prison for li...

FBI Mafia Informants Joseph Barboza Raymond Patriarca Jerry Angiulo Hitman

February 07, 2022

"They're After Me Like a F*ing Animal" - Jerry Angiulo - The Early Days

Boston crime czar Jerry Angiulo kept a tight inner circle and only worked with his brothers when he started out. Initially confining their activities to bookmaking, the Angiulo enterprise expanded into money lending, restaura...

Mafia Joseph Barboza Boston Raymond Patriarca Jerry Angiulo

January 31, 2022

Family Feud - The Hill - Part 2

As the Gang War in Boston heated up, the gang on Federal Hill in Providence, Rhode Island, had a feud of their own going on. But this time it was very much a family affair. Featuring the crimes and family drama of the Baccari...

Mafia Raymond Patriarca Baccari Jack Nazarian

January 24, 2022

La "Causa" Nostra - The Hill - Part 1

In March 1962, the FBI installed a wiretap at New England mafia boss Raymond Patriarca's office in Providence, Rhode Island. The Coin-O-Matic on Atwells Ave. was Grand Central Station with people coming to Raymond with their ...

FBI Mafia Raymond Patriarca Jerry Angiulo Henry Tameleo Providence

January 17, 2022

Uncle Sam Needs You - Cuba, The Mafia, Castro & JFK

In this episode, we will be discussing the Mafia's role in Cuba, the various plots to kill Castro and theories about the assassination of President Kennedy. Follow us on Twitter for sneak peeks of upcoming episodes. You can a...

FBI Mafia Castro CIA JFK Sam Giancana Johnny Roselli Santo Trafficante

January 10, 2022

Top Echelon Informant Program - License to Kill

A gang war raged in Boston throughout the 1960s, and everyone was forced to choose a side. You were either with the McLaughlins or the McLeans. The FBI picked a side too. But in their effort to wipe out the “Italian faction” ...

FBI Informants Jimmy Flemmi Joseph Barboza Stevie Flemmi H. Paul Rico Dennis Condon John Kehoe Vincent Teresa Boston

January 03, 2022

Maurice "Pro" Lerner - Not Your Average Hitter" - The Early Years

Alleged mafia hitman and CIA recruit Maurice Pro Lerner compiled a batting average of .308 with 24 home runs and 225 RBI over the course of his 482 game baseball career. But he was just as well known for his antics off the fi...

Maurice "Pro" Lerner Jack "Red" Kelley Billie Aggie Hitman

December 31, 2021

New Year's Eve Bonus Episode - Dorothy Barchard - Boston's Black Widow

In today's bonus episode, Lara and Nina are discussing Dorothy Frances Barchard. Dorothy was infamous for her lovers and crimes. And the trail of inmates and corpses she left behind. Follow us on Twitter for sneak peeks of up...

FBI Informants

December 27, 2021

Billie Aggie - The Plymouth Mail Robbery Investigation Begins

Jack Kelley's former partner, Billie Aggie, returns to star as the Postal Inspectors' "Expert" Investigator in the Plymouth Mail Robbery. Billie introduces Maurice "Pro" Lerner into Jack's circle, but Jack is one step ahead o...

FBI Informants Jack "Red" Kelley Plymouth Mail Robbery

December 20, 2021

The Great Plymouth Mail Robbery

Last week we told you how the Plymouth Mail Robbery job dropped into Jack Kelley's lap in a Watertown diner, and introduced you to the Dream Team Jack assembled to take down the largest cash score in history. This week Jack d...

Jack "Red" Kelley Plymouth Mail Robbery Carmello Merlino Richard Chicofsky Sonny Diaferio Thomas Richards Roy Appleton Robberies

December 13, 2021

Plymouth, More Than Just a Rock - The Planning of the Plymouth Mail Robbery

Still considered unsolved, the Plymouth Mail Robbery was the largest cash heist of all time when it was carried out in 1962. Jack "Red" Kelley was producer, architect, director, and the lead in its performance. We take you be...

Jack "Red" Kelley Plymouth Mail Robbery Carmello Merlino Richard Chicofsky Sonny Diaferio Thomas Richards Roy Appleton Robberies

December 06, 2021

Lessons Learned and Not - Heists of the 1930s

A constant “student” of crime, Jack Kelley analyzed other crimes not to replicate them, but rather not to repeat their mistakes. We are taking one last journey to the 1930s to examine some of the lessons Jack took away from h...

Boston Robberies Bank Robbers

November 29, 2021

On the Waterfront - The Boston Version

We are taking a deep dive into the origins of the McLean McLaughlin Gangland War of the 1960s. A war for territory marked by boxing matches, attempted car bombings, and the murder of more than 60 men. The Boston FBI Office al...

FBI Informants McLean McLaughlin Buddy McLean Winter Hill Punchy McLaughlin George McLaughlin Bernie McLaughlin