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

This video is Part Two of my History of the Pittsburgh Mob series, focusing on Gregorio Conti, widely regarded as Pittsburgh’s second Mafia boss. Conti matters because he sits at a critical turning point in the city’s underworld—when loose Black Hand extortion begins giving way to something more centralized, disciplined, and ultimately more dangerous. Quiet, calculating, and outwardly respectable, Conti helped shape the early structure of organized crime in Western Pennsylvania—and then became one of its most revealing casualties. The episode opens on September 24, 1919, in Pittsburgh’s Strip District. It’s a mild fall morning, coal smoke hanging low, streetcars rattling over cobblestones. Conti—mid-forties, round-faced, horn-rimmed glasses—sits behind the wheel of his automobile, sweating under pressure. 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 15th. He should already be gone. Instead, he delays for one last, unnecessary errand: selling his car. The “buyers” arrive—men he knows. Handshakes. Small talk. Then they climb inside. As the car rolls along Smallman Street, the conversation fades. A revolver clicks. Four shots tear through the morning. Conti collapses over the steering wheel and dies minutes later. The coroner later records the cause as shock and hemorrhage from gunshot wounds to the heart, time of death 11:20 a.m. At first, police default to the era’s familiar explanation: the Black Hand. But the killing feels too precise, too controlled. This looks like business. From there, the episode rewinds to show how Conti rose—and why his power was already fraying. Born in Comitini, Sicily in 1873, Conti grows up in a world where authority is local and protection comes from men, not the state. He immigrates to the United States in 1907, becomes a naturalized citizen in 1910, and settles in Pittsburgh alongside relatives and trusted associates. He builds a wine and liquor operation that looks legitimate on the surface but quietly functions as a nerve center 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, the chemist who keeps the operation running behind the scenes, and Nicola “Nick” Gentile, a relative and seasoned underworld diplomat physically present in Pittsburgh between 1910 and 1920. Family tension, shifting alliances, and Conti’s need to dominate begin creating cracks—just as the stakes are about to rise. All of this unfolds under the shadow of Prohibition. The Eighteenth Amendment is ratified in January 1919, Pennsylvania ratifies weeks later, and the Volstead Act follows that fall. For a man positioned at the center of alcohol distribution, it should be an opportunity. Instead, Conti liquidates assets, winds down his business, and prepares to leave the country—raising uncomfortable questions about how secure his position really is. After the murder, detectives chase multiple theories. One centers on an alleged $5,500 whiskey swindle involving bottles filled with Allegheny River water. Another points to a long-simmering feud rooted in a clerical error on a $4,000 federal bond, which left produce merchants J.C. and Philip Catalano financially exposed after Conti’s nephew fled to Italy. Witnesses place multiple familiar figures at the scene, and arrests come quickly—but certainty never does. In the end, the case collapses. On November 12, 1919, a coroner’s jury exonerates the men held in connection with the killing. No shooter is officially identified. The murder of Gregorio Conti remains unsolved. Conti’s funeral is quiet, handled by James J. Flannery Brothers Company and believed to end with burial at Cavalry Cemetery—a stark contrast to the spectacle that followed the death of Salvatore Catanzaro just a few years earlier. And yet, Conti’s death doesn’t slow Pittsburgh’s underworld. It clears the way. Into that vacuum steps a younger, harder figure—Stefano “Big Steve” Monastero—and with him begins Pittsburgh’s most violent and profitable Mafia era. But that… is a story for another day. 00:00:00 Start 00:04:03 Theme Music 00:05:31 Intro 00:08:25 Gregorio Conti's Early Life & Rise 00:37:03 The Quiet War with the Camorra 00:46:57 The Valentine Piazza Hit 00:58:18 The Death of Gregorio Conti