Underbelly

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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.

Entropy Media


    • Mar 12, 2025 LATEST EPISODE
    • infrequent NEW EPISODES
    • 38m AVG DURATION
    • 30 EPISODES
    • 2 SEASONS


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    Latest episodes from Underbelly

    "Underbelly: Killing Kurt" Official Trailer - Premieres April 2nd!

    Play Episode Listen Later Mar 12, 2025 1:58


    For years, Kurt Calabrese lived under the violent rule of his father, feared Chicago hitman Frank “The Breeze” Calabrese Sr. But when his brother turned informant, their family—and the Chicago Outfit—began to fall apart. The betrayal led to a historic trial, exposing decades of unsolved murders and taking down some of the most powerful mob figures in modern history. But behind the headlines was an even darker story—one of family loyalty, fear, and survival. Now, for the first time, Kurt reveals what it was really like growing up in the mob, the impossible choices he faced, and what it took to escape. The award winning franchise "Underbelly", returns for its long-awaited 3rd season. The all new season of Underbelly: Killing Kurt premieres April 2nd with a two-episode debut. Subscribe or follow now so you don't miss it! Available wherever you get your podcasts. Learn more about your ad choices. Visit podcastchoices.com/adchoices

    Introducing "Game Plan: The Wendell Brown Story" - Out Now!

    Play Episode Listen Later Aug 14, 2024 1:50


    A special look at the trailer for "Game Plan: The Wendell Brown Story," the newest podcast from Entropy Media. Episodes 1 & 2 available now! (Links Below) Synopsis: After his pro football career ended, college star Wendell Brown moved to China to teach his beloved sport to youth abroad. But when the Detroit legend is assaulted at a 2016 party in the Yuzhong District, he's the one charged with a crime. With little hope of being released by a court boasting a 99% conviction rate, Wendell must survive the Chinese prison system––one of thirty men in a cramped, single-toilet cell, and the sole Black man, American, and foreigner behind bars. He only manages to endure thanks to the fortitude football taught him—and the daring rescue mission by a group of strangers from around the world who organize through WeChat and take great risks to bring him home. The all new series "Game Plan: The Wendell Brown Story" is available now, wherever you listen to podcasts! Listen Now... Apple: https://podcasts.apple.com/us/podcast/game-plan-the-wendell-brown-story/id1753345801 Spotify: https://open.spotify.com/show/0R0o0kkYCmYsJ2LTrU6XUf?si=d7188bb91b88475b Amazon Music: https://music.amazon.com/podcasts/f59467cd-630b-4c0a-b4ce-c41c649c467c/game-plan-the-wendell-brown-story iHeart Radio: https://www.iheart.com/podcast/269-game-plan-the-wendell-brow-189067311/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

    S2 E12: The Other Side of Town

    Play Episode Listen Later Jun 5, 2024 38:49


    Dave Rupert retires to a life in hiding, reflecting on a journey that took him across the Atlantic and back. We visit an icon of Belfast that shows just how much the north has changed. We reflect on what Dave contributed to the peace in Ireland and whether a reunited Ireland could be possible in our lifetime.  Learn more about your ad choices. Visit megaphone.fm/adchoices

    S2 E11: McKevitt v. Pallasch

    Play Episode Listen Later May 29, 2024 43:16


    Dave Rupert's contract was just for intelligence gathering, but now he's asked to testify in court. Will he out himself as an agent and informer, furthering putting himself and his family in danger? When Mickey McKevitt faces charges under a new law in the Irish Special Criminal Court, his lawyers are going to have to dig deep to discredit a potential witness. That's when they get wind of a book deal back in Chicago.  Learn more about your ad choices. Visit megaphone.fm/adchoices

    S2 E10: Spying on Mickey

    Play Episode Listen Later May 22, 2024 37:02


    After years of hard work and learning the ins and outs of Irish republicanism, Dave Rupert is in with the Real IRA. He's rubbing shoulders with one of the most dangerous men in Ireland. Dave is fast friends with the man who Irish and British governments say is the terrorist who must be stopped to prevent another tragedy like Omagh. Dave knows how to work his angles, but he worries about whether the security services can keep up.  Learn more about your ad choices. Visit megaphone.fm/adchoices

    S2 E09: The Two Mickeys

    Play Episode Listen Later May 8, 2024 42:26


    The last militant Republicans still willing to fight after the Omagh bombing are looking for support. What better support could you ask for than a wealthy American offering cash and weapons from the United States? Joe O'Neil introduces Dave Rupert to a storied Republican named Mickey Donnelly and with that connection, Dave is whisked off to a meeting with the Real IRA's top man: Mickey McKevitt. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S2 E08: Omagh

    Play Episode Listen Later May 1, 2024 44:19


    A car bomb explosion kills 31 people -- including unborn twins -- in the town center of Omagh in Northern Ireland. The Real IRA takes public responsibility for the bombing, but the story that trickles out maintains it was a horrible mistake. In this episode, we explore the aftermath of the bombing that infuriated Irish from coast to coast, north and south. Meanwhile, Dave Rupert is suddenly in real danger as any IRA associates become public enemies and a central target of security services.  Learn more about your ad choices. Visit megaphone.fm/adchoices

    S2 E07: Good Friday

    Play Episode Listen Later Apr 24, 2024 43:07


    On Good Friday in 1998, a treaty that will come to be called the Good Friday Agreement is signed by several nations. At its core, it's an a plan for peace that will involve a decommissioning process for paramilitary groups and a plan for a future vote on a united Ireland. For some, it's about forgiveness, hope and peace. For others, it's the same old story: another surrender to British Authority. Dave Rupert has a front row seat for the final significant fracturing of militant Republicans of the 20th century. Where does he go from here? Learn more about your ad choices. Visit megaphone.fm/adchoices

    S2 E06 The City That Dyes its River Green

    Play Episode Listen Later Apr 17, 2024 46:08


    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

    S2 E05: Coin Operated

    Play Episode Listen Later Apr 10, 2024 50:52


    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

    S2 E04: It's a Funny Place, Tullaghan

    Play Episode Listen Later Apr 3, 2024 46:10


    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

    S2 E03: The FBI Walks Into a Bar

    Play Episode Listen Later Mar 27, 2024 46:33


    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

    S2 E02: A Little Bit Off Base

    Play Episode Listen Later Mar 20, 2024 45:30


    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

    S2 E01: There Once Was A Trucker From Chicago

    Play Episode Listen Later Mar 13, 2024 44:11


    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

    Underbelly: The Rebel Kind Trailer - Out March 13

    Play Episode Listen Later Feb 29, 2024 3:44


    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. From Entropy Media, the second season of the Underbelly series focuses on the unlikely man with entrepreneurial dreams and a willingness to do whatever it takes to get the job done. Veteran journalists Bob Herguth and Abdon Pallasch tell the story through tape recordings they made of Rupert in secret locations 20 years ago. Premieres everywhere podcasts are found Wednesday, March 13. Learn more about your ad choices. Visit megaphone.fm/adchoices

    Underbelly S1 Brokers, Bagmen, & Moles: Live Q&A in Chicago

    Play Episode Listen Later Oct 26, 2023 69:37


    Underbelly creator & host Anjay Nagpal, showrunner Danielle Elliot, "Brokers, Bagmen, & Moles" book co-author David Greising, and traders/fan favorites Tim, Stretch, & T-Bun got together at the Texas Taco Bar in Chicago to have a live panel discussion and Q&A. If you missed it, you can still enjoy hearing about the origins of the investigation, the struggles & successes bringing it to life in audio, a few more stories from the floor—and some strong opinions about what happened on that floor (and no, not just from T-Bun). Learn more about your ad choices. Visit megaphone.fm/adchoices

    Join Us LIVE in Chicago, Tuesday October 3!

    Play Episode Listen Later Sep 27, 2023 1:57


    Join host Anjay Nagpal and special guests from Brokers, Bagmen, & Moles for a live panel discussion and Q&A! We'll share stories from behind-the-scenes of the production, answer your burning questions about the wild stuff that went down on the trading floor, and share some laughs (and tacos). This FREE event will be at the Texan Taco Bar in Chicago's West Loop (942 W Randolph St), next Tuesday, October 3, from 5-6:30pm. Space is limited, and we'll be prioritizing RSVPs that come with a question. Share yours by DMing us @entropymediaco or emailing us social@entropymedia.art. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 12: The Durkin Document

    Play Episode Listen Later Jul 19, 2023 55:16


    Trying to find more concrete evidence that the FBI was actually on the floor to investigate the ties between organized crime and Chicago's exchanges, Anjay searches through thousands of pages of court transcripts. What he finds isn't quite what he was looking for—instead, he discovers a legal brief that leads him down a completely unforeseen and even more shocking path. What happened to this smoking gun, and why was nothing ever done about these disturbing allegations? Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 11: A Humble Accountant

    Play Episode Listen Later Jul 12, 2023 45:38


    More stories of mob ties among traders come to the surface, so Anjay decides to call one more agent—the one with a background in organized crime, and who seems most willing to speak with him: Dietrich Volk. Anjay arrives in a remote part of Colorado to interview the former agent, and at long last, we learn the truth of this investigation. By the end of their conversation, Anjay thinks he might be able to prove what the agents never could. Notes: Head to DRINKAG1 dot com slash BROKERS to get a FREE one-year supply of AG Vitamin D3+K2, plus five AG1 Travel Packs with your first purchase of AG1! You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 10: How to Buy An Industry

    Play Episode Listen Later Jun 28, 2023 43:47


    As the trials wrapped up, Congress held a series of hearings that questioned how these markets should be regulated. In echoes of those trials, Congressmen displayed varying levels of comprehension of how the Merc & CBOT worked, and it turns out that those who did understand might be a little too familiar with the heads of those exchanges. As the inquiry winds down, clear winners and losers emerge. Meanwhile, Anjay has a phone call that sets us up for brand-new conclusions about the origins of the investigation. *We will be off next week for the Fourth of July and returning Wednesday, July 12th with the next episode.* Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 09: It Was All Chaos

    Play Episode Listen Later Jun 21, 2023 49:34


    Defense attorneys come out swinging, in an attempt to whip up a furor over the dozens of charges against Merc traders. But they have a tough time getting jurors to understand how the buying and selling of future contracts work—not to mention keeping them awake—and the trials descend into chaos. In the end, how many traders were found guilty? And how do the agents who worked the case view its legacy now? Anjay has the surprising answers, and some new questions. Notes: Head to DRINKAG1 dot com slash BROKERS to get a FREE one-year supply of AG Vitamin D3+K2, plus five AG1 Travel Packs with your first purchase of AG1! You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 08: Just Be Yourself

    Play Episode Listen Later Jun 14, 2023 55:12


    After nearly eight months of off-the-record conversations, two FBI agents agree to speak with Anjay on the record. Randy Janett and Mike Bassett tell Anjay their side of the story. They're open about why this investigation ended when it did, but when it comes to what inspired the FBI to send agents to the floor in the first place, will they stick with the public narrative, or will they reveal some cracks in it? Notes: Head to DRINKAG1 dot com slash BROKERS to get a FREE one-year supply of AG Vitamin D3+K2, plus five AG1 Travel Packs with your first purchase of AG1! You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 07: Big Fish

    Play Episode Listen Later Jun 7, 2023 46:56


    The man, the myth, the target of this investigation? That's Lewis Borsellino… at least, according to Lewis Borsellino. The son of a mafia hitman, Borsellino made a name for himself as one of the most successful traders in the S&P 500 futures pit. That got the Feds interested in him, or so the story goes. Borsellino tells Anjay he suspects there's more to it than that, and Anjay decides there is only one way to get answers: speaking with the FBI agents themselves. Notes: You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 06: Traders and Traitors

    Play Episode Listen Later May 31, 2023 41:17


    Someone was bound to talk eventually, and it ended up being one of the white-collar kids at the Chicago Board of Trade. Anjay speaks with trader Dave Skrodzki about his decision to cooperate, what it meant for his livelihood, and why Skrodzki thinks the government found exactly what it was looking for in Chicago. While Skrodzki and a few other cooperators helped the FBI solidify a few cases, the Feds ultimately didn't produce nearly as many indictments as they'd promised. If their plan was to work their way up the ladder, it wasn't working. So where can they look to next? Notes: You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 05: The Informant?

    Play Episode Listen Later May 17, 2023 37:54


    Within a week of breaking the story, the press learned that the FBI came to Chicago's exchanges partly in response to a complaint from a powerful agricultural company called Archer Daniels Midland. While that remains the popular narrative, Anjay's sources convince him that the government has managed for decades to keep something about this case secret—but what, exactly? In this episode, we learn about the government's attempts to get T-Bun and Ray Pace to cooperate with the investigation, and Anjay gets in touch with the guy who did. Notes: You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 04: Scapegoats and Fat Cats

    Play Episode Listen Later May 10, 2023 45:06


    Pulitzer prize-winning journalist Bill Crawford broke the news of the undercover investigation in January 1989, when an unnamed source in Washington, D.C. tipped off the Chicago Tribune. The Trib's initial stories billed the case as a tremendous win for the government, but right away, Crawford questioned if the government had missed its mark—could they perhaps have been gunning for the men in charge of the exchanges? Anjay then speaks with a former trader who worked closely with the longtime Merc boss, Leo Melamed, to learn about the underhanded political dealings that enabled the stunning transformation of this sleepy agricultural exchange—and the systemic corruption that followed. Notes: You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 03: Knock Knock. Who's There?

    Play Episode Listen Later May 3, 2023 38:50


    The ‘80s were a time of tremendous growth on the floor, creating opportunities for guys like boxer Ray Pace. Ray went from working part-time on movie sets to trading for one of the largest brokerage groups at the Merc, ABS Partners. Little did he know, by 1987, he was standing next to an undercover agent. In the grand scheme of things, Ray was a small fish, so Anjay questions if his role with the controversial ABS is what put him on the Feds' radar. The agents say he committed felonies; Ray says he was just doing business the way he was taught. All this leads Anjay to a new idea: Was Ray just a scapegoat, a way for the FBI to cover up its own failure? Notes: You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 01: The Biggest Small Town in the World

    Play Episode Listen Later Apr 26, 2023 35:27


    In the 1980s, blue collar kids started making millions at Chicago's commodities exchanges. This century-old boys' club was one of the best-kept secrets in the world until the FBI showed up and tried to end the party. The FBI investigation put the exchanges on front pages everywhere, but when the Feds packed up, business went back to usual—like they'd never been there. Thirty years later, former-trader-turned-Hollywood exec Anjay Nagpal thinks there's something strange about this case. He taps his Chicago connections and after a few calls, he's already poking holes in the government's long-accepted narrative of the investigation. Notes: You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit megaphone.fm/adchoices

    S1 02: T-Bun and the G Men

    Play Episode Listen Later Apr 26, 2023 39:48


    To understand this case, you need to meet the colorful cast of characters at its core: Chicago commodities traders. Meet part-time bookie, possible mob associate, and full-time trader Tony “T-Bun” Bonjourno. He's a blue collar guy whose dad's friend helped him get a job on the floor. Once there, T-Bun and his friends live a life beyond their wildest fantasies. T-Bun gives us our first glimpse of the FBI agents' actions on the floor and tells an incredible story that might just be the answer to why this investigation ended prematurely. Notes: You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit megaphone.fm/adchoices

    Underbelly: Brokers, Bagmen, & Moles - Season 1 Trailer

    Play Episode Listen Later Apr 4, 2023 2:38


    When you picture the 1980s' Wall Street boys' club, you might not think of Chicago. But in 1987, its Mercantile Exchange dwarfed the New York Stock Exchange in both dollars and international influence. Member-owned and expanding rapidly, how it worked—or who was working it—was more obscured. That's when the FBI stepped in. The Feds sought to shine light upon it through a high-stakes operation, the most expensive in its history, to expose corruption at Chicago's Merc and Board of Trade. What ensued was an elaborate undercover investigation resulting in dozens of indictments for traders who were accused of conspiring to defraud farmers, banks, pension funds, and other customers from around the world. The government either had itself a huge success that reformed our financial markets, or it was total flop—it all depends who you ask. Led by host Anjay Nagpal, after more than thirty years, Brokers, Bagmen, & Moles gets to the truth. Learn more about your ad choices. Visit megaphone.fm/adchoices

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