Lara Chicofsky & Nina Jobe

Double Deal - True Stories of Criminals, Crimes and Lies

History EN ↓ 95 episodes

My name is Lara Chicofsky, and my cohost is Nina Jobe. We created this podcast to shine a light on some of the lesser known characters and crimes in Boston and New England. We've spent the past two years researching the Boston crime scene primarily focusing on the 1960s. There are many podcasts and books available about organized crime in the Boston area, but ours is a bit different. I spent most of my life in my father’s world. Eavesdropping when I was a kid, listening intently when he was at the end of his life. I often took what he said with a grain of salt. He was, after all, a conman, an...

Author

Lara Chicofsky & Nina Jobe

Category

History

Podcast website

www.doubledealpodcast.com

Latest episode

Jan 30, 2026

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Episodes

Billie Aggie - The Plymouth Mail Robbery - The Investigation Begins 27.12.2021

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 of them. Episode 1 - Jack Kelley Episode 4 - Roy Appleton Episode 5 - Carmello Merlino & Sonny Diaferio Episode 8 & 10 - Richard Chicofsky (Tommy Richards can be found...

The Great Plymouth Mail Robbery 20.12.2021

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 decides on a date and the team executes his plan. Meanwhile, Richie works with the FBI and Narcotics Agents in a sting operation. Episode 1 - Jack Kelley Episode 4 - Roy Applet...

Plymouth, More Than Just a Rock - The Planning of the Plymouth Mail Robbery 13.12.2021

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 behind the scenes to see how Jack and his Dream Team came together to plan and organize the heist. Episode 1 - Jack Kelley Episode 4 - Roy Appleton Episode 5 - Carmello Merlino...

Lessons Learned and Not - Heists of the 1930s 06.12.2021

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 his own experiences and those of his contemporaries, some of whom would later be arrested for the 1950 Brink's heist. For a transcript of this episode visit our website . Follo...

On the Waterfront - The Boston Version 29.11.2021

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 also chose sides in the conflict, which led to Richie becoming a Confidential Informant for SA H Paul Rico in 1961. For a transcript of this episode visit our website . Follow u...

Thanksgiving Bonus Episode - Prison Breaks 24.11.2021

Meet 4 men who made it their mission to escape from behind bars. Learn what happened to them once they gained their freedom. Lots of happy endings in today's episode. For a transcript of this episode visit our website . Follow us on Twitter for sneak peeks of upcoming episodes. You can also find us on Instagram and Facebook . Questions or comments, email lara@doubledealpodcast.com or nina@doublede...

Disorganized Crime - Raymond Patriarca - The Early Days 22.11.2021

Raymond L.S. Patriarca is infamous in his role as the Boss of the New England Mafia for nearly 30 years. Join us this week as we talk about Patriarca's early life of crime, and the many failures along the way to his rise to power. For a transcript of this episode visit our website . Follow us on Twitter for sneak peeks of upcoming episodes. You can also find us on Instagram and Facebook . Question...

The Founding Fathers - Organized Crime in Early 20th Century Boston 15.11.2021

Starting with the days when the Camorra ruled Boston, we introduce the Sicilian men who toppled them: Don Nene Terruso, Don Pepino Modica, Don Filippo Bruccola, and more. And don't miss Lara's personalized food tour of Boston, sharing some of her favorite restaurants and the best food to order there. For a transcript of this episode visit our website . Follow us on Twitter for sneak peeks of upcom...

An Unconfidential Informant - Richie Chicofsky - Part 2 08.11.2021

Richie gets out of jail and returns to work for Mafia boss Ralphie Lamattina. He also starts robbing banks with Jack Kelley, and gun running. A not-so-chance meeting with FBI Special Agent H Paul Rico leads him to a crossroads. Now he must make a decision that will change his life forever. For a transcript of this episode visit our website . Follow us on Twitter for sneak peeks of upcoming episode...

Hoover's All American Boys 01.11.2021

Meet the men of the Boston FBI office who comprised the special task force that was created to solve the Great Brink's Heist of 1950. Five of these men would go on to form the organized crime task force charged with bringing down the Mafia in New England. For a transcript of this episode visit our website . Follow us on Twitter for sneak peeks of upcoming episodes. You can also find us on Instagra...

An Institute of Higher Learning - Richie Chicofsky - The Early Years 25.10.2021

In this episode Nina and Lara will be discussing Richie Chicofsky's early years, and his first prison stint. Fats Buccelli's son Bobby, the DeSisto home invasion and Richie's first encounter with SA H. Paul Rico will be included. If you'd like to email Lara you can reach her at lara@doubledealpodcast.com and Nina can be contacted at nina@doubledealpodcast.com For show notes and supporting material...

Moldy Loot - Fats Buccelli, Wimpy Bennett & the Brink's Money 18.10.2021

The only money from the Brink's robbery ever recovered was found in June 1956. $57K of rotted and moldy cash wrapped in old newspapers was discovered behind a wall in an office on Tremont Street. Join us this week as we discuss how the Feds located the loot and what happened next. Lara also reveals how Edward Wimpy Bennett came by his nickname. If you'd like to email Lara you can reach her at lara...

The CI Program & H. Paul Rico - The Early Days 11.10.2021

We are introducing Richie's nemesis in our story this week: H Paul Rico. Join us as we cover the early years of Rico's life and FBI career. We're also talking about the FBI's Confidential Informant Program and some of its early victories and blunders. If you'd like to email Lara you can reach her at lara@doubledealpodcast.com and Nina can be contacted at nina@doubledealpodcast.com For show notes a...

The Bobbsey Twins - Santo Diaferio & Carmello Merlino - The Early Days 04.10.2021

In Episode 5 we will be discussing Sonny Diaferio and Mello Merlino, childhood friends and lifelong partners in crime. Nina and Lara will be telling the story of their early days. If you'd like to email Lara you can reach her at lara@doubledealpodcast.com and Nina can be contacted at nina@doubledealpodcast.com For show notes and supporting materials please visit our website and click on episode 5....

Conman to Armorer - Roy Appleton - The Early Years 27.09.2021

In Episode 4 we will be discussing Roy Appleton. The man who from his grave would be the beginning of the end for former FBI SA, H. Rico. Rico who spent his final days in prison, just as many of the men he put away. Nina and Lara will tell you about Roy's early days. If you'd like to email Lara you can reach her at lara@doubledealpodcast.com and Nina can be contacted at nina@doubledealpodcast.com...

The Great Brink's Heist - Our Take On It 20.09.2021

The Great Brink's Heist of 1950 was almost the perfect crime. $2.775 million was stolen in Boston on a mid-January evening. We follow the twists and turns of the FBI investigation that led to the capture and eventual conviction of eight local men who had long criminal records. We conclude with our own theories about what really happened. If you'd like to email Lara you can reach her at lara@double...

My Getaway Car Was A Lawnmower - Billie "Aggie" 12.09.2021

We heard a little bit about Billie Aggie in episode 1. Today we will be discussing two more of Billie's heists, and how he found himself voted out of Walpole State Prison.

Let's Go To The Track! - John J. "Red" Kelley - The Early Years 06.09.2021

Jack Kelley was called "Swiss watch" for the precision with which he planned robberies. But a simple trip to the race track led to his first arrest. This episode will cover the early years of John J. Kelley's criminal career. We will discuss several of his early robberies and how a trip to the race track lands him in prison. You can find us on Twitter , Facebook and Instagram . If you'd like to em...

Preview Episode 9 - Richie Chicofsky 04.09.2021

A sneak preview of Episode 9! Hear about Richie Chicofsky, the central figure in our podcast series Double Deal.

Double Dealer - Trailer 29.08.2021

Hi all! Thank you for tuning in. Our first episode will launch on Monday, September 6, 2021.

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