Kurt Calabrese grew up in the Chicago mafia known as The Outfit. His father, Frank Calabrese Sr, was the premier hitman, known for strangling his victims with his bare hands. But Frank didn't just leave the violence at work. He trained his sons Kurt and Frank Jr in the mob enforcer life since they were kids, through fear, intimidation and horrific abuse.

When the entire Calabrese family got locked up for extortion, his other son, Frank Jr, who had battled a bad drug problem and stolen hundreds of thousands of dollars from his dad, wrote a letter to the feds and offered to wear a wire on his own father.

Enter the infamous Family Secrets trial in Chicago. Kurt's father, who brutally abused him for years, is about to face numerous murder charges. His brother is about to become the most infamous rat in Chicago’s history. And Kurt is caught right in the middle of his family…and the biggest organized crime trial in Chicago’s history. 

This is a special presentation of Season 3 of the Underbelly Podcast, Killing Kurt...produced by Underworld host Danny Gold.

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Will Grant, the BBC’s Mexico, Central America and Cuba correspondent, was recently on the ground at Jalisco’s Rancho Izaguirre, dubbed ‘Mexico’s Auschwitz’, and CECOT, Nayib Bukele’s megaprison in El Salvador. Will spoke to Sean about what he saw in both places, how politics and organized crime is coverging, what new Mexican President Claudia Scheinbaum can do without triggering full-scale war — and how populism and the mob have often gone hand-in-hand across Latin America.

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He’s a recluse, a cockfighting high-roller, a former cop and a maniac. But will Nemesio Oseguera Cervantes, aka El Mencho, do what he’s been threatening for years and become the most powerful cartel boss on the planet? From avocados to abogados, weed to coke to fentanyl, Mencho is a narco so bloodthirsty his men are compared to ISIS. Can the Mexican state cut him down to size? Or will a lifelong quest to build a citadel in his home state of Michoacan come off, ruling local civilians with a sadistic iron fist? We look at the past, present and future of who might just be the scariest criminal we’re profiled on this show.

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South Africa's secretive Numbers Gangs almost defy description; they're one part cult, one part religion, and all parts violent psychopaths. Emerging originally as bandits preying on gold miners and policemen in colonial South Africa, they took shape in the brutal prison system of apartheid, where sometimes the only way to communicate was through stabbing whoever was around.

What formed was something more than a gang, it was almost a shadow universe where every single interaction was governed by the archaic and complex rules of the 26's, 27's and 28's. And when apartheid crumbled, and South Africa's drug markets opened up, the numbers gangs traded in their generations of rituals and rules to merge with powerful street gangs and bring the grim reality of South Africa's torturous prison out into the world.

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Sean Williams reports from the Philippines, where former President Rodrigo Duterte’s brutal drug war cost up to 30,000 lives and tore Philippine society to shreds. But was it all cover for his family’s own involvement in the drug trade? Reporting from Duterte’s stronghold of Davao, where he ran a decades-long death squad, and capital Manila, which bore the brunt of that bloody blueprint, we expose the genesis of the war — and its longtime link to Triads and other criminal groups. 

Duterte's connections to the drug trade have rarely been reported on in English and are just starting to make waves. This episode, backed by exclusive sources and firsthand accounts, challenges mainstream narratives and sheds new light on one of the most controversial anti-drug campaigns in modern history.

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The Ghost Shadows are said to have been the wildest of Chinatown's gun-toting teenage gangs in the 1970's and 1980's, engaging in countless shootouts with their rivals the Flying Dragons and the White Eagles. And that was before they linked up with one of the Triad-connected tongs to run the neighborhood protection and gambling rackets, earning millions every year despite being barely out of their teens.

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When they finally went down on RICO charges in the mid 80's, they were tied to 13 murders. But it wasn't the rival gangs that tore the Ghost Shadows apart; it was a power struggle between the street generals that proved to be the biggest challenge. And it's then when Peter Chin arrived on the scene to claim the role of Dai Lo, or big brother.

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When Adnan Khashoggi, Saudi arms dealer and self-styled world’s richest man, met with US officials to discuss the Ayatollah, it may have seemed like a chance to cash in corporate power for political clout. But the affair — and an ill-advised friendship with the kleptocratic leaders of the Philippines — would send Khashoggi’s businesses into a tailspin, and land him jail.

What came next was one of the most spectacular court cases of the era. And it finally shined a spotlight on the life and legends of a man whose lavish lifestyle was the envy of world leaders, and an up-and-coming Donald Trump.

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The Dixie Mafia terrorized the southern US for decades before authorities were finally able to bring them down. Starting off as a loose collective of career criminals who specialized in burglaries and robberies, they grew more organized after starting to use the infamous Biloxi strip of undercover brothels and gambling houses as a base, eventually shifting to everything from drug smuggling to contract killing to even running national romance scams.

We're joined by Jed Lipinski of Gone South to break down everything from carnie robberies to corrupt sheriffs and murdered judges.

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Adnan Khashoggi was born in Mecca — but his life was anything but pious. The billionaire had multiple wives, girlfriends and armies of callgirls, not to mention gambling sessions and club nights whose costs ran into the millions of dollars.

Khashoggi made his first riches shipping arms from the US to Saudi Arabia. But soon his “fees,” and the ways he got them, began to catch up with him. And dalliances in politics, bad investments, and some friends in dark places, would send the life of the ‘world’s richest man’ into a criminal tailspin.

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Michael Miske came from a broken home through years of petty crime to lead a gang of lost boys in Honolulu, cornering its drug scene and befriending cops to build an empire of pain in the Aloha State.

But when Miske’s son slammed his car into a truck and died, it sent the kingpin on a spiral of misplaced rage — ending in murder, conspiracy and even a chemical weapon attack. Even when the law caught up with him, Miske had one last trick up his sleeve.

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