24 episodes

Underbelly is a podcast series exploring the wild and true stories behind investigations into the underbelly of society. From enigmatic spies, to seedy criminals and crooked officials, to the upper echelons of government intelligence, we shine light on the underworld through never before heard revelations about crimes you never dared to imagine.

Season one of Underbelly—Brokers, Bagmen, & Moles—takes a fresh look at the FBI's most expensive undercover operation in history. Told through archival audio as well as new and exclusive interviews with the people who were there, this financial thriller features host Anjay Nagpal investigating whether the Feds' 1987 attempt at exposing widespread corruption at Chicago's future exchanges was a huge success... or a massive failure. It all depends who you ask.

Season two of Underbelly, premiering March 13—The Rebel Kind—is the unreal, real-life story of Dave Rupert, a six-foot-seven Chicago trucker who infiltrated the heart of a dangerous faction of the Irish Republican Army. Veteran journalists Bob Herguth and Abdon Pallasch tell you the story of how this unlikely man with entrepreneurial dreams and a willingness to do whatever it takes ends up being the most famous/infamous spy during The Troubles through tape recordings they made of Rupert in secret locations 20 years ago.

Underbelly Entropy Media

    • True Crime
    • 5.0 • 250 Ratings

Underbelly is a podcast series exploring the wild and true stories behind investigations into the underbelly of society. From enigmatic spies, to seedy criminals and crooked officials, to the upper echelons of government intelligence, we shine light on the underworld through never before heard revelations about crimes you never dared to imagine.

Season one of Underbelly—Brokers, Bagmen, & Moles—takes a fresh look at the FBI's most expensive undercover operation in history. Told through archival audio as well as new and exclusive interviews with the people who were there, this financial thriller features host Anjay Nagpal investigating whether the Feds' 1987 attempt at exposing widespread corruption at Chicago's future exchanges was a huge success... or a massive failure. It all depends who you ask.

Season two of Underbelly, premiering March 13—The Rebel Kind—is the unreal, real-life story of Dave Rupert, a six-foot-seven Chicago trucker who infiltrated the heart of a dangerous faction of the Irish Republican Army. Veteran journalists Bob Herguth and Abdon Pallasch tell you the story of how this unlikely man with entrepreneurial dreams and a willingness to do whatever it takes ends up being the most famous/infamous spy during The Troubles through tape recordings they made of Rupert in secret locations 20 years ago.

    There Once Was A Trucker From Chicago

    There Once Was A Trucker From Chicago

    Meet Dave Rupert. A guy born in a part of Upstate New York so rural it's practically Canada, with a past nearly as untamed: trucker, one-time professional wrestler, pilot, a bit of a serial entrepreneur. Meet Mickey McKevitt. An ocean away, he leads the Irish Republican Army's militant splinter cell, the Real IRA. The two men had seemingly nothing in common, but by the time they met, Dave had earned the trust of the group as though he was an Irishman himself. Meet Bob Herguth and Abdon Pallasch, reporters who interviewed Rupert in secret locations over twenty years ago to find out about their first meeting.
    Learn more about your ad choices. Visit megaphone.fm/adchoices

    • 44 min
    A Little Bit Off Base

    A Little Bit Off Base

    When an FBI agent walks into Dave Rupert's truck stop, his mind starts racing. There's so many things law enforcement might want to address. A few friends he made though a dalliance is the last thing on his mind. Dave Rupert's unusual background in upstate New York led from a family doing what they had to do to survive to becoming a trucking entrepreneur. But a night out at a bar in Florida will eventually change Dave's life. 
    Additional Music by Guinness the Duo. 
    Learn more about your ad choices. Visit megaphone.fm/adchoices

    • 45 min
    The FBI Walks Into a Bar

    The FBI Walks Into a Bar

    Dave Rupert experiences a little indigestion as he mulls over an offer from the FBI. He'll learn the agent who approached him has a background in investigating international terrorism back in Chicago. In fact, Ed Buckley is well known to Irish Republican supporters in the city. When Dave sees an opportunity to make some money, he goes for it. 
    Learn more about your ad choices. Visit megaphone.fm/adchoices

    • 46 min
    It's a Funny Place, Tullaghan

    It's a Funny Place, Tullaghan

    Dave's plot to run a bar for profit while spying on vacationing republicans along the banks of the Drowes River is a rocky as the road to Dublin. The former owner of his pub wasn't paying the bills and that makes Dave's life even more difficult. But a diligent barkeep certainly doesn't look like a spy and his plan kind of begins to work. Knowing the history of the British occupation in Ireland is just the tip of the iceberg for Dave's education on republican ideals. 
    Learn more about your ad choices. Visit megaphone.fm/adchoices

    • 46 min
    Coin Operated

    Coin Operated

    A visit to Dave's family in upstate New York gets Bob and Abdon a history lesson on Joe Beef, Joby for short. That was Dave's nickname growing up in rural Madrid and it stuck with his family through his litany of careers. Even through late 1997 when Dave inks his first official contract to become a spy -- affording him the opportunity to finally focus on the danger in militant republican circles. 
    Learn more about your ad choices. Visit megaphone.fm/adchoices

    • 50 min
    The City That Dyes its River Green

    The City That Dyes its River Green

    Dave Rupert has spent years earning the trust of his IRA friends in Ireland and they've finally given him a military task. Dave heads back to Chicago with a name: Frank O'Neill. He's about to discover why an FBI agent like Ed Buckley was tasked with rooting out any connections between Chicago and militant Republicans. Dave's next moves will be in a city that goes as far as dyeing a whole river green on St. Patrick's Day. 
    Learn more about your ad choices. Visit megaphone.fm/adchoices

    • 46 min

Customer Reviews

5.0 out of 5
250 Ratings

250 Ratings

Creator54356 ,

Enjoying season 1

Great season 1. As a retail trader I find this story to be very eye-opening and enjoyable

I B A Dougherty ,

My Review

I found this podcast not only very interesting, but really well put together and enjoyable.
The small smattering of Irish history was also a great backdrop for the story too.
I can’t wait for more!

Tim Rooney the best app critic ,

Great story

Love the history lesson.

Top Podcasts In True Crime

Status: Untraced
Tenderfoot TV & Audacy
Beyond All Repair
WBUR
Dateline NBC
NBC News
Crime Junkie
audiochuck
Morbid
Morbid Network | Wondery
MrBallen Podcast: Strange, Dark & Mysterious Stories
Ballen Studios

You Might Also Like

The Underworld Podcast
The Underworld Podcast
Original Gangsters, a True Crime Talk Podcast
Original Gangsters, a True Crime Talk Podcast
Deep Cover: The Nameless Man
Pushkin Industries
The Big Dig
GBH
Gangland Wire
Gary Jenkins: Mafia Detective
The Daily Show: Ears Edition
Comedy Central & iHeartPodcasts