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

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. 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, Stefano and Sam quietly build something far more organized, powerful, and dangerous—an expanding criminal network rooted in bootlegging, extortion, violence, and control of the city’s illicit liquor trade. But before the Monasteros become Pittsburgh’s closest equivalent to Al Capone, their story begins decades earlier in Sicily and New Orleans. This episode traces the family’s origins in Caccamo, Sicily, the infamous assassination of New Orleans Police Chief David C. Hennessy in 1890, and the shocking lynching of Stefano and Sam’s father, Pietro Monastero, during the Parish Prison mob violence of 1891—one of the largest mass lynchings in American history. From there, we follow the Monastero family’s journey to Pittsburgh, where the brothers become deeply connected to the city’s growing Mafia networks through the fruit and produce trade, the Pittsburgh Fruit Exchange, and the rapidly expanding underground economy created by Prohibition. This episode also explores: • The collapse of Pittsburgh’s early Mafia leadership after Gregorio Conti’s murder • The rise of Pittsburgh’s Prohibition bootlegging economy • The Monasteros’ connections to figures like Salvatore Catanzaro, Nicola Gentile, Salvatore Calderone, and Nicasio Landolina • The growth of the Pittsburgh Fruit Exchange and the brothers’ warehouse operations in the Strip District • The mysterious 1920 bombing near the Monastero organization • Loreto Monastero’s shocking murder case, asylum commitment, and escape • The emergence of early Mafia hierarchy and initiation rituals in Pittsburgh • The rise of Stefano Monastero as Pittsburgh’s dominant bootlegging boss • The violent murder of Luigi “The Big Gorilla” Lamendola and the growing underworld war surrounding the Monasteros By the mid-1920s, Stefano and Sam Monastero are no longer simply participating in Pittsburgh’s underworld—they are reshaping it. What emerges during this period is the foundation of the modern Pittsburgh Mafia. This episode is based on extensive research using immigration records, newspapers, census documents, court records, FBI files, historical archives, and firsthand family accounts to reconstruct one of the most important—and least understood—chapters in organized crime history. Subscribe to The Gangland History Podcast for more deep dives into Prohibition, La Cosa Nostra, Mafia history, and the forgotten underworld history of Pittsburgh. 00:00 The Shooting of New Orleans Police Chief David C. Hennessy 06:12 Episode Theme Song 07:39 Episode Intro 12:24 The Rise of the Monasteros 16:38 The New Orleans Connection 24:27 The Death of New Orleans Police Chief David C. Hennessy 30:34 The 1891 Hennessy Murder Trial 31:46 The 1891 Parish Prison Riot & The Death of Pietro Monastero 34:48 Aftermath of the 1891 New Orleans Lynching 51:46 The Path from Caccamo to Pittsburgh 53:43 The Corleone Family Comparison 01:02:46 The Loreto Monastero Situation 01:11:52 Building an Empire: The Pittsburgh Fruit Exchange 01:19:21 Building an Empire: Fruit, Produce, and Prohibition 01:43:30 Introducing Luigi "The Big Gorilla" Lamendola 01:51:51 The Murder of Luigi Lamendola 02:05:34 Episode Closing