Pittsburgh’s vibrant Strip District is beloved for its eclectic markets, trendy eateries, and bustling streets. However, beneath its colorful surface lies a fascinating, shadowy past marked by bootlegging, organized crime, and legendary mobsters. This intriguing underworld history dates back to Prohibition (1920–1933), a time when the federal ban on alcohol inadvertently fostered a thriving black market and widespread criminal activity.
Let’s take a journey back through time and explore some historic locations in the Strip District, where notorious gangsters once held court. Some of these sites still stand today; others survive only in the record, offering visitors a tangible connection to Pittsburgh’s criminal legacy.
Setting the Stage: Prohibition-Era Pittsburgh
When Prohibition took effect in January 1920, alcohol consumption didn’t stop; instead, it went underground. Organized crime syndicates swiftly moved into the lucrative bootlegging business. Pittsburgh, strategically located near waterways and railroad lines, became a hotbed for illegal liquor trade, gambling rings, and speakeasies. Rival gangs frequently clashed over territories, and violence spilled into the streets.
Pittsburgh was called “the wettest spot in the United States.”
The Strip’s geography suited smugglers. A narrow ribbon of land hemmed in by the Allegheny River on one side and a ridge on the other, it funneled goods in and out of the city through a dense concentration of railroad spurs, river docks, warehouses and freight infrastructure. That legitimate daytime commerce was the perfect cover for an illicit nighttime economy.
In the early years, Sicilian-born gangster Joseph Siragusa, known as the “Yeast Baron,” became Pittsburgh’s leading bootleg boss by supplying the yeast and corn sugar that fed the region’s home stills.
The Volpe Brothers Murders (1932)
On July 29, 1932, brothers John, James and Arthur Volpe, bootleggers from Wilmerding, were shot to death at the Rome Coffee Shop (see below). John was gunned down on the sidewalk outside; James and Arthur were killed inside.
Police suspected John Bazzano, who had become the city’s leading racketeer after Joseph Siragusa’s murder in 1931. Although the original building no longer exists, visitors to the area can still sense the echoes of that violent day (read more about John Bazzano’s ruthless reign).
Wholey’s Building: A Cold Storage Hideaway
Now known as Wholey’s Market at 1711 Penn Avenue, this large structure built in 1928 originally served as the Federal Cold Storage Building. During Prohibition, its refrigerated rooms were rumored to store more than just seafood. Legend has it the mob utilized these cold rooms to discreetly store and distribute bootlegged liquor, hidden among legitimate shipments.
Though today shoppers are busy selecting fresh seafood, few realize the building figures in the neighborhood’s Prohibition lore.
The Rome Coffee Shop: Scene of the Volpe Murders
The Rome Coffee Shop stood at 704 Wylie Avenue in the Lower Hill District, outside the Strip. It is remembered today almost entirely as the scene of the 1932 Volpe murders.
The building is gone, cleared along with much of the Lower Hill in the redevelopment of the 1950s.
Senator John Heinz History Center: Documenting Mob History
At 1212 Smallman Street, the Heinz History Center preserves material on the region’s Prohibition and organized crime history, making it a worthwhile stop for history enthusiasts seeking deeper insights.
The Show Boat: A Floating Speakeasy
Pittsburgh’s best-known Prohibition nightspot floated. The Show Boat, a speakeasy and gambling boat moored on the Allegheny River Downtown, ran openly until federal Prohibition agents raided it on May 15, 1930, in one of the city’s biggest liquor raids.
Organized crime didn’t disappear after repeal; it adapted, pivoting to gambling and other rackets. The LaRocca era and the rise of organized crime in Pittsburgh picks up the story from there.
Strip District’s Secret Tunnels and Basements
Less known to the public are the underground networks beneath the Strip District. Tunnels and basements once provided secret routes for smuggling alcohol and other contraband. These hidden passageways facilitated discreet movement of bootleggers, enhancing their ability to evade law enforcement.
The Strip District’s old warehouses and factories were riddled with sub-basements, steam utility corridors, coal delivery tunnels and underground passages dating back to the neighborhood’s industrial buildout. During Prohibition, these spaces became the infrastructure of an underground economy in the most literal sense. Some buildings reportedly had trapdoors leading to sub-basements, creating double-layered hiding places for liquor caches.
Proving specific tunnels definitively is difficult. After repeal, the tunnels that had ferried whiskey went back to being coal delivery chutes and utility corridors, and many were sealed off.
Walking Through Mob History: Tours Today
The modern Strip District embraces its storied past; local guides have offered walking tours of its Prohibition history, so check current schedules before you go. Guides recount vivid stories of bootlegging, gang wars, and notable mob hits. Participants traverse historic locations, enhancing their understanding of Pittsburgh’s layered past.
Such tours have covered former speakeasy sites and bootlegger routes. To see how the neighborhood got from there to here, the transformation of the Strip District traces the full arc, and Pittsburgh’s oldest bars and the history behind them connects those threads to establishments still standing today.
Fascinating Lesser-Known Mob Facts
- Days after the Volpe murders, John Bazzano was summoned to New York; on August 8, 1932, his body was found in a burlap sack in Red Hook, Brooklyn. He was reportedly killed because the Volpe hit had not been sanctioned, though accounts differ.
Conclusion: Reflections on a Dark Past
Today, the Strip District stands as a vibrant symbol of Pittsburgh’s cultural and economic resurgence. However, its colorful past remains embedded in every brick and alleyway. By exploring these iconic mobster hideouts, visitors gain a richer appreciation for the complex, sometimes dark forces that shaped Pittsburgh into the thriving city it is today.
More Secret Tunnels, Mafia Haunts, and Underworld Lore
The Strip District’s back-alley hideouts are just the beginning. Dive into our full Pittsburgh Mafia & Crime History collection to meet the mobsters who used these spaces—and the empires they built from the shadows.
From notorious dons like John Bazzano to high-stakes heists and the rise of the LaRocca family, this hub maps the full extent of Pittsburgh’s criminal underworld.
Explore the Full Crime History →
