Underbelly: Killing Kurt

S3 E08: The Final Errand

Wed, 14 May 2025 09:13:00 -0000

In the final chapter of Killing Kurt, Kurt Calabrese travels to a remote house in North Carolina to confirm his father’s death. What begins as a simple errand turns into an emotional reckoning. Inside a dim room behind a red curtain, Kurt comes face to face with the body of Frank Calabrese Sr.—the man who dominated, abused, and haunted his life. For the first time, Kurt is able to speak freely to his father, unleashing years of pain, rage, and conflicted love.

As Kurt seeks closure, the fallout from Operation Family Secrets continues. Federal agents raid Frank Sr.’s home and uncover hidden stashes of cash, diamonds, guns, and tapes—evidence of a criminal empire now reduced to dust. With the Outfit in decline and the family fractured beyond repair, Kurt reflects on what it truly means to survive a legacy built on violence, fear, and silence.

Binge the entire season of Killing Kurt—along with other gripping Entropy Media shows—completely ad-free by subscribing to Entropy Unlimited on Apple Podcasts. Unlock exclusive access to bonus content and enjoy your favorite stories without interruptions. Click ⁠⁠⁠HERE ⁠⁠⁠to learn more!

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S3 E07: I Will Be Praying For Your Soul

Wed, 07 May 2025 10:44:00 -0000

As Kurt Calabrese tries to settle into life after prison, ominous threats begin to arrive—dead rats on his porch, anonymous letters, and a staged bomb at his home—signs someone in the Outfit suspects he’s cooperating with the Feds. While he denies involvement, suspicion falls on his father and the father's girlfriend, Diane, whose presence near Kurt’s home the night of the rat incident raises red flags.

The threats escalate just as the landmark Operation Family Secrets trial kicks off, charging multiple high-ranking Chicago mobsters with 18 murders. It’s a case built on unprecedented betrayal, with mob sons turning on their fathers—and Kurt caught in the crossfire of a family and a criminal empire coming undone.

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S3 E06: Brotherly Love

Wed, 30 Apr 2025 13:01:00 -0000

In 1998, Frank Calabrese Jr. makes the most dangerous decision of his life: he writes a letter to the FBI offering to turn against his own father—one of the most feared mob enforcers in Chicago history. What follows is one of the most audacious undercover operations in the history of organized crime.

In this episode, we go inside the moment that changed everything for the Calabrese family and the Chicago Outfit. After being transferred to the same prison as his father, Junior realizes the only way to escape is to cooperate. He offers to wear a wire inside federal prison, hoping to capture Frank Calabrese Sr. incriminating himself in decades of unsolved mob murders.

Told through secret recordings, FBI testimony, and Junior’s own words, this is the story of how one son risked his life to dismantle the family empire he was born into. It’s also the origin of the evidence that would form the heart of the Family Secrets case—the case that brought down the Outfit.

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S3 E05: The Letter

Wed, 23 Apr 2025 14:32:00 -0000

In 1995, the FBI's years-long investigation into the Chinatown crew comes to a head with sweeping indictments and early morning raids. With their criminal empire crumbling, the Calabrese family faces the full weight of the justice system—and begins to turn on itself.

This episode tells the harrowing story of what happens when loyalty becomes a liability. Junior faces a 30-year prison sentence. Kurt is offered a deal: serve two years, and his brother, father, and uncle all get reduced sentences. Despite a lifetime of abuse at the hands of his father, Kurt agrees—sacrificing his own freedom for the sake of family.

But even behind bars, Frank “The Breeze” Calabrese Sr. remains in control—cutting financial support to his sons’ families and manipulating Kurt into continuing the family’s illicit business. With a handshake deal and no paperwork to protect his loved ones, Kurt finds himself once again used by the man he trusted least.

As prison walls close in, and brother turns against brother, Kurt reflects on what it truly means to make a deal with the devil—and what’s left when the devil doesn’t keep his end.

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S3 E04: Take the Money and Run

Wed, 16 Apr 2025 09:00:00 -0000

A duffel bag filled with mob cash disappears—and with it, any remaining trust between Kurt Calabrese, his brother Junior, and their volatile father, Frank “The Breeze” Calabrese.

Kurt’s loyalty is tested like never before when his father shows up unannounced, ready to retrieve what he believes is still safely hidden in the bank. But when Frank discovers the money is gone, suspicion quickly turns to rage—and all roads lead to Junior. What follows is a brutal confrontation on a suburban lawn, a devastating confession, and the unraveling of a family already under intense FBI surveillance.

As Frank becomes more unhinged, Kurt is pulled deeper into his father's dangerous world, forced to collect debts and even contemplate arson—pushed to the brink of committing crimes he never wanted to be a part of. Meanwhile, Junior’s decisions spiral out of control, dragging friends, businesses, and his own freedom into the fallout.

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S3 E03: Where Did Matt Go?

Wed, 09 Apr 2025 11:45:00 -0000

By the early 1990s, Frank Calabrese Sr. had spent decades building a criminal empire fueled by fear, paranoia, and control. He taught his sons the art of survival in the mob—never use house phones, memorize payphone numbers, speak in code, and trust no one. But when Frank let his guard down for an indebted auto shop owner named Matt Russo, the cracks in his armor started to show.

What Frank saw as an opportunity to exploit a failing business, the FBI saw as the perfect way in. Russo, drowning in debt and desperate, became a federal informant and began wearing a wire in Frank’s inner circle. But gathering evidence on a man as cautious—and dangerous—as Frank Calabrese wouldn’t be easy. We go inside the FBI’s high-stakes operation to take Frank down, the meticulous way Frank shielded himself from betrayal, and the moment it all started to unravel.

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S3 E01: I'll Kick You So Hard You'll Walk Funny

Wed, 02 Apr 2025 09:00:00 -0000

Kurt Calabrese, son of notorious Chicago Outfit hitman Frank "The Breeze" Calabrese Sr., breaks his silence about growing up under the shadow of one of Chicago's most feared mob enforcers. His story begins with a dramatic courtroom confrontation during the historic "Family Secrets" trial, where Kurt's victim impact statement provoked his father's menacing outburst, revealing the monster that had terrorized him throughout his childhood.

Growing up in Elmwood Park, a Chicago suburb known as an enclave for Outfit members, Kurt lived a double life—neighbors saw his father as a friendly figure who handed out homemade wine, while behind closed doors, Kurt endured relentless abuse, living in constant fear of his father's return. Frank Sr. broke the traditional Outfit code by bringing his sons into "the life," forcing Kurt to collect "street tax" and teaching him disturbing techniques for violence. This first chapter of Kurt's story reveals the beginning of his journey from terrified son to someone who would ultimately help bring down one of Chicago's most notorious crime families.

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S3 E02: The Man Is Nuts

Wed, 02 Apr 2025 09:00:00 -0000

The complicated relationship between Kurt Calabrese and his Uncle Nick reveals how Nick became a surrogate father figure in Kurt's turbulent childhood. While Kurt's father Frank Sr. ruled through fear, Uncle Nick showed kindness—despite his increasingly dark role as an outfit hitman who would eventually participate in multiple murders for the Chicago mob. Uncle Nick was reluctantly pulled into the criminal underworld by his brother Frank Sr., who in turn answered to feared outfit captain Angelo "The Hook" LaPietra.

Kurt's life changes dramatically when he falls in love with Angela, the granddaughter of his father's boss Angelo LaPietra. Despite family pressure to stay apart, Kurt and Angela secretly marry at City Hall—a decision that sends Frank Sr. into a violent rage. What should have been a joyful wedding day turns into a terrifying chase through the streets as Kurt flees his father's wrath, culminating in a chilling warning from Uncle Nick that this forbidden marriage could get them all killed. Their story provides a haunting glimpse into how the Chicago outfit's brutal code affected even the most personal aspects of its members' lives.

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"The Rebel Kind" BONUS: An interview with David Rupert (Happy St. Patrick's Day!)

Mon, 17 Mar 2025 20:48:00 -0000

In advance of the Season 3 premiere of Underbelly on April 2nd, Entropy Media brings you a special BONUS episode of The Rebel Kind in honor of St. Patrick’s Day—a story deeply tied to Ireland’s turbulent past and one man’s extraordinary role in shaping its future.

For the first time ever, David Rupert—the trucker-turned-international-informant who helped take down Real IRA leader Mickey McKevitt—breaks his silence in a rare and candid interview.

After spending years in witness protection, David reached out upon hearing Underbelly: The Rebel Kind and agreed to sit down with Abdon Pallasch and Bob Herguth, the journalists who first documented his extraordinary story. In this special bonus episode, David reflects on his double life, the high-stakes world of counterterrorism, and the personal cost of his undercover work. He also reveals what it’s like to live off the grid—and shares some jaw-dropping stories you won’t hear anywhere else.

Listen now, and for more exclusive content from Underbelly and other Entropy Media podcasts, subscribe to Entropy Unlimited on Apple Podcasts. And don’t miss the Season 3 premiere of Underbelly: Killing Kurt, on April 2nd.

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

Wed, 12 Mar 2025 10:00:00 -0000

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.

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

Wed, 14 Aug 2024 09:30:00 -0000

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/

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S2 E12: The Other Side of Town

Wed, 05 Jun 2024 10:10:00 -0000

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.

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S2 E11: McKevitt v. Pallasch

Wed, 29 May 2024 10:10:00 -0000

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.

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S2 E10: Spying on Mickey

Wed, 22 May 2024 10:10:00 -0000

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.

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S2 E09: The Two Mickeys

Wed, 08 May 2024 10:10:00 -0000

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.

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S2 E08: Omagh

Wed, 01 May 2024 10:10:00 -0000

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.

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S2 E07: Good Friday

Wed, 24 Apr 2024 10:10:00 -0000

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?

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S2 E06: The City That Dyes its River Green

Wed, 17 Apr 2024 10:10:00 -0000

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.

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S2 E05: Coin Operated

Wed, 10 Apr 2024 10:10:00 -0000

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.

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S2 E04: It's a Funny Place, Tullaghan

Wed, 03 Apr 2024 10:10:00 -0000

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.

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S2 E03: The FBI Walks Into a Bar

Wed, 27 Mar 2024 10:00:00 -0000

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.

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S2 E02: A Little Bit Off Base

Wed, 20 Mar 2024 10:56:00 -0000

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.

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S2 E01: There Once Was A Trucker From Chicago

Wed, 13 Mar 2024 10:10:00 -0000

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.

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Underbelly: The Rebel Kind Trailer - Out March 13

Thu, 29 Feb 2024 14:00:00 -0000

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.

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

Thu, 26 Oct 2023 07:05:00 -0000

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).

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Join Us LIVE in Chicago, Tuesday October 3!

Wed, 27 Sep 2023 10:05:00 -0000

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.

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S1 12: The Durkin Document

Wed, 19 Jul 2023 07:05:00 -0000

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?

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S1 11: A Humble Accountant

Wed, 12 Jul 2023 07:05:00 -0000

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.

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S1 10: How to Buy An Industry

Wed, 28 Jun 2023 07:05:00 -0000

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.*

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S1 09: It Was All Chaos

Wed, 21 Jun 2023 07:05:00 -0000

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.

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S1 08: Just Be Yourself

Wed, 14 Jun 2023 07:05:00 -0000

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.

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S1 07: Big Fish

Wed, 07 Jun 2023 07:05:00 -0000

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.