The Gangland History Podcast: An Organized Crime & Mafia History Podcast

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 is a true crime podcast hosted by Jacob Stoops, with 50 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Jacob Stoops hosts The Gangland History Podcast: An Organized Crime & Mafia History Podcast, a true crime show with 50 episodes published.

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  The Gangland History Podcast: An Organized Crime & Mafia History Podcast

  #49: History of the Pittsburgh Mob (Part Four): The Rise of the Monastero's

  May 29, 20262h 7mS0

  <p>In this episode of The Gangland History Podcast’s ongoing History of the Pittsburgh Mob series, we explore the rise of the Monastero brothers—Stefano “Big Steve” Monastero, Salvatore “Sam” Monastero, and their older brother Loreto—as Pittsburgh’s underworld transforms during the violent early years of Prohibition.</p><p><br></p><p>At the center of the story are Stefano and Sam Monastero, two brothers who rise from immigrant beginnings to become the dominant force in Pittsburgh’s bootlegging empire during the 1920s. While Pittsburgh’s underworld fractures after the deaths of early leaders like Gregorio Conti and Martin M. Burke, Ste...

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  The Gangland History Podcast: An Organized Crime & Mafia History Podcast

  #48: History of the Pittsburgh Mob (Part Three): Prohibition, Bootlegging, Bullets, and the “Bootleg Kings”

  Mar 18, 20262h 19mS0

  <p>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. 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 u...

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  The Gangland History Podcast: An Organized Crime & Mafia History Podcast

  #47: History of the Pittsburgh Mob (Part Two): The Rise & Fall of Gregorio Conti

  Jan 28, 20261h 43mS0

  <p>This episode is Part Two of The Gangland History Podcast’s History of the Pittsburgh Mob, focusing on Gregorio Conti, widely regarded as Pittsburgh’s second Mafia boss. 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 September 24, 1919, in Pittsburgh’s Strip District. It’s a mild fall morning, coal smoke hanging low as streetcars rattle over cobbleston...

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  The Gangland History Podcast: An Organized Crime & Mafia History Podcast

  #46: History of the Pittsburgh Mob (Part One): Immigration, the Black Hand, and the Era of Salvatore Catanzaro

  Dec 24, 20251h 5mS0

  <p>Long before Prohibition, long before speakeasies and Tommy guns, Pittsburgh’s underworld was already taking shape—quietly, violently, and largely unseen.</p><p>This episode traces the true origins of organized crime in Western Pennsylvania, beginning not with a Mafia family as we know it today, but with knives in an alley, whispered threats, and fear used as a business model. We open on October 28, 1892, when a brutal Sicilian knife duel erupts on a dusty Pittsburgh street—an encounter that nearly kills Salvatore “The Banana King” Catanzaro and sets the tone for everything that follows.</p><p>From there, the story...

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  The Gangland History Podcast: An Organized Crime & Mafia History Podcast

  #45: History of the Tampa Mob: A Discussion with Author, Scott Deitche

  Oct 8, 20251h 14mS0

  <p>In this episode of The Gangland History Podcast, host Jacob Stoops interviews acclaimed author and Mafia historian Scott Deitche, one of the nation’s foremost experts on organized crime in Florida and the Trafficante crime family.</p><p>Together, they trace the full evolution of the Tampa Mafia — from its earliest days under Ignazio Italiano, through decades of bloody rivalries, Cuban connections, and political intrigue, to its quiet decline under the final generation of mob leadership.</p><p>The conversation begins with the waves of Italian immigration to Tampa’s Ybor City and the cigar industry that built both the ec...

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