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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Stefano Monastero.

His story—and the next phase of Pittsburgh’s underworld—is just beginning.

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.

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 cobblestones. Somewhere along Smallman Street, 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.

His wife and children are already packed for the 10:10 p.m. train to New York, with plans to sail for Italy on October 15, 1919. 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. Four shots tear through the enclosed space. Conti collapses over the steering wheel and dies minutes later. The coroner records the cause as shock and hemorrhage from gunshot wounds to the heart, with the time of death listed as 11:20 a.m.

At first, police default to the familiar explanation: the Black Hand. 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.

From there, the episode rewinds to trace Conti’s rise. Born in Comitini, Sicily, in 1873, 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 1907, becomes a naturalized citizen in 1910, 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 801 Wylie Avenue as the Pittsburgh Wine and Liquor Company.

The episode explores Conti’s inner circle, including his nephew Giuseppe “Peppino” Cusumano, a trained chemist and pharmacist, and Nicola “Nick” Gentile, a relative and underworld diplomat physically present in Pittsburgh between 1910 and 1920. Family tension, shifting alliances, and questions of respect begin to fracture Conti’s control from within.

All of this unfolds under the shadow of Prohibition. The Eighteenth Amendment is ratified in January 1919, Pennsylvania follows weeks later, and the Volstead Act 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.

After the murder, detectives pursue competing theories, including an alleged $5,500 whiskey swindle and a feud rooted in a clerical error on a $4,000 federal bond involving produce merchants J.C. and Philip Catalano. Arrests come quickly, explanations pile up, but certainty never does.

On November 12, 1919, a coroner’s jury exonerates 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 Cavalry Cemetery.

Conti’s death doesn’t slow Pittsburgh’s underworld—it clears the way. Into that vacuum steps Stefano “Big Steve” Monastero, ushering in the city’s most violent and profitable Mafia era.

But that… is a story for another day.