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

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.