The Gangland History Podcast, hosted by history buff and mob aficionado, Jacob Stoops. He tells the true crime biographies of real life mobsters and dives deep into the plots, sub-plots, and real facts behind Cosa Nostra as well as popular mob films and television shows. Formerly called The Members-Only Podcast.
The Gangland History Podcast: An Organized Crime & Mafia History Podcast
Claim This Podcastby Jacob Stoops
4.7(163 reviews)
50 episodes
Updated Bi-weekly
Accepts GuestsHas SponsorsLocation 🇺🇸
56
Podcast Authority
BetaFairBased on show quality, social media presence, reviews, charts, and more
Quality37
Social0
YouTube93
Engagement93
Podcast Overview
The Gangland History Podcast, hosted by history buff and mob aficionado, Jacob Stoops. He tells the true crime biographies of real life mobsters and dives deep into the plots, sub-plots, and real facts behind Cosa Nostra as well as popular mob films and television shows. Formerly called The Members-Only Podcast.
Language
🇺🇲
Publishing Since
8/30/2021
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56
Podcast Authority
BetaFairBased on show quality, social media presence, reviews, charts, and more
Quality37
Social0
YouTube93
Engagement93
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excellent
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1h 54m
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180 reviews (4.7/5.0)
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Recent Episodes
May 29, 2026
#49: History of the Pittsburgh Mob (Part Four): The Rise of the Monastero's
Host Patrick O'Donnell explores the Monastero brothers' rise to power in Pittsburgh's bootlegging empire during Prohibition, detailing their Sicilian origins and violent ascent.
March 18, 2026
#48: History of the Pittsburgh Mob (Part Three): Prohibition, Bootlegging, Bullets, and the “Bootleg Kings”
<p><strong>This video is Part Three of my History of the Pittsburgh Mob series, focusing on Prohibition and the rise of Pittsburgh’s early bootleg kings—men like Martin M. Burke who transformed decades of political influence, saloon ownership, and neighborhood control into large-scale criminal enterprises. </strong>Picking up in the aftermath of Gregorio Conti’s 1919 assassination, this episode explores how the vacuum he left behind becomes the foundation for a far more violent and organized underworld.</p><p>The episode opens with a chaotic, real-life gun battle on Pittsburgh’s streets. Rogue bootleggers, posing as Prohibition agents, attempt to move liquor under the cover of authority—until they are confronted by federal agent Andrew Carciere. What follows is a high-speed chase, gunfire, and arrests, capturing the instability of the early Prohibition years. The rules are unclear, enforcement is inconsistent, and in that confusion, opportunity thrives.</p><p>From there, the episode examines both sides of the equation—the criminals building a new underground economy and the men attempting to stop them. Enforcement efforts are shaped by figures like Prohibition Director John D. Pennington and Treasury Secretary Andrew W. Mellon, but even with federal attention, authorities struggle to keep pace with rapidly evolving bootlegging networks.</p><p>At the same time, the episode revisits the leadership vacuum created by Conti’s death. With no clear successor, attention turns to figures like Giuseppe “Peppino” Cusumano, Nicola “Nick” Gentile, and Salvatore Calderone. None immediately consolidate control, contributing to a fragmented and competitive early Prohibition landscape.</p><p>As alcohol is driven underground, Pittsburgh’s existing infrastructure adapts quickly. Saloons become speakeasies, political relationships remain intact, and distribution networks evolve rather than disappear. Demand never fades—it simply becomes illicit.</p><p>In this environment, bootlegging is scattered and competitive. Crews clash over territory and supply, while schemes involving forged federal permits reveal how operators exploit the system itself. Even when exposed, these operations prove difficult to dismantle, underscoring the limits of enforcement.</p><p>Within this shifting landscape, Martin M. Burke rises to prominence. Born in 1871 and shaped by decades in the saloon trade, Burke enters Prohibition prepared. Alongside his brothers, he builds a network of saloons, properties, and entertainment venues in the Hill District, centered around Wylie Avenue and Fullerton Street.</p><p>When alcohol goes underground, Burke converts what already exists. His saloons become speakeasies, his properties serve as distribution hubs, and his political connections provide insulation. In a city filled with small operators, he stands out for his ability to organize and scale, emerging as one of Pittsburgh’s first true bootleg kings.</p><p>But as profits grow, so does competition. Shipments are hijacked, armed guards protect deliveries, and disputes escalate into violence that spreads beyond the city into surrounding towns. Bootlegging becomes a capital-intensive, interconnected underground industry.</p><p>And within that system, the men who survive begin to evolve. They learn that structure is more profitable than chaos, refining their operations and building networks that move toward greater organization. Prohibition becomes a proving ground for the next phase of organized crime.</p><p>Martin Burke represents a critical step in that evolution—a bridge between the old world of saloons and ward politics and the emerging world of large-scale bootlegging. But his removal creates yet another vacuum, and like the one before it, it will not remain empty.</p><p>Because by the late 1920s, chaos begins to give way to consolidation. And among the figures positioned to take advantage of that shift is a man whose rise has been building in the background.</p><p>Stefano Monastero.</p><p>His story—and the next phase of Pittsburgh’s underworld—is just beginning.</p>
January 28, 2026
#47: History of the Pittsburgh Mob (Part Two): The Rise & Fall of Gregorio Conti
<p>This episode is <strong>Part Two</strong> of The Gangland History Podcast’s <strong>History of the Pittsburgh Mob</strong>, focusing on <strong>Gregorio Conti</strong>, widely regarded as <strong>Pittsburgh’s second Mafia boss</strong>. Conti matters because he emerges at a turning point, when loose Black Hand extortion and ethnic feuding begin giving way to something more centralized, disciplined, and dangerous. Quiet, calculating, and outwardly respectable, Conti helped shape that transition—and then became one of its earliest casualties.</p><p>The story opens on <strong>September 24, 1919</strong>, in Pittsburgh’s Strip District. It’s a mild fall morning, coal smoke hanging low as streetcars rattle over cobblestones. Somewhere along <strong>Smallman Street</strong>, Conti sits behind the wheel of his automobile, sweating under pressure. He’s in his mid-forties, round-faced, heavyset, horn-rimmed glasses slipping down his nose—the kind of man who could pass for a schoolteacher. But Conti isn’t teaching today. He’s trying to leave Pittsburgh for good.</p><p>His wife and children are already packed for the <strong>10:10 p.m. train to New York</strong>, with plans to sail for Italy on <strong>October 15, 1919</strong>. He should already be gone. Instead, he delays for one last, unnecessary errand: selling his automobile. The buyers arrive—men Conti knows. Hands are shaken. Pleasantries exchanged. Then they climb inside. As the car rolls down Smallman Street, the conversation fades. A revolver clicks. <strong>Four shots</strong> tear through the enclosed space. Conti collapses over the steering wheel and dies minutes later. The coroner records the cause as <strong>shock and hemorrhage from gunshot wounds to the heart</strong>, with the <strong>time of death listed as 11:20 a.m.</strong></p><p>At first, police default to the familiar explanation: the <strong>Black Hand</strong>. But the killing feels too precise and controlled. There’s no extortion letter, no public threat, no warning meant to terrorize a neighborhood. This looks less like chaotic revenge and more like business.</p><p>From there, the episode rewinds to trace Conti’s rise. Born in <strong>Comitini, Sicily</strong>, in <strong>1873</strong>, he grows up in a world where authority is local and protection comes from men rather than the state. He immigrates to the United States in <strong>1907</strong>, becomes a <strong>naturalized citizen in 1910</strong>, and settles in Pittsburgh with relatives and trusted associates. He builds a wine and liquor operation that appears legitimate but quietly functions as a hub for influence, credit, and enforcement, eventually anchoring at <strong>801 Wylie Avenue</strong> as the <strong>Pittsburgh Wine and Liquor Company</strong>.</p><p>The episode explores Conti’s inner circle, including his nephew <strong>Giuseppe “Peppino” Cusumano</strong>, a trained chemist and pharmacist, and <strong>Nicola “Nick” Gentile</strong>, a relative and underworld diplomat physically present in Pittsburgh between <strong>1910 and 1920</strong>. Family tension, shifting alliances, and questions of respect begin to fracture Conti’s control from within.</p><p>All of this unfolds under the shadow of <strong>Prohibition</strong>. The <strong>Eighteenth Amendment</strong> is ratified in <strong>January 1919</strong>, Pennsylvania follows weeks later, and the <strong>Volstead Act</strong> is passed that fall. For a man positioned at the center of alcohol distribution, it should have been an opportunity. Instead, Conti liquidates assets, winds down his business, and prepares to leave the country.</p><p>After the murder, detectives pursue competing theories, including an alleged <strong>$5,500 whiskey swindle</strong> and a feud rooted in a <strong>clerical error on a $4,000 federal bond</strong> involving produce merchants <strong>J.C. and Philip Catalano</strong>. Arrests come quickly, explanations pile up, but certainty never does.</p><p>On <strong>November 12, 1919</strong>, a coroner’s jury <strong>exonerates</strong> the men held in connection with the killing. No shooter is officially identified. Gregorio Conti’s murder remains unsolved. His funeral is quiet, with burial believed to have taken place at <strong>Cavalry Cemetery</strong>.</p><p>Conti’s death doesn’t slow Pittsburgh’s underworld—it clears the way. Into that vacuum steps <strong>Stefano “Big Steve” Monastero</strong>, ushering in the city’s most violent and profitable Mafia era.</p><p>But that… is a story for another day.</p><p></p>
50 total episodes available with 1 transcripts
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- What is The Gangland History Podcast: An Organized Crime & Mafia History Podcast?
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This podcast updates bi-weekly.
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