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

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.