Chicago: The Terrible Genna Brothers

The Genna Brothers were six brothers who operated in the Chicago area through the Prohibition era from 1921 until 1925. By mid-1925, three of the six Genna brothers had been killed and the Genna Crime Family had been absorbed by the Chicago Outfit.

Despite being a prominent and violent part of the Chicago underworld for several years, the Genna Brothers aren’t often spoken about. Yet their actions — particularly the murder of Dean O’Banion — set off a chain of events that would ultimately lead to the St. Valentine’s Day Massacre of 1929.

The Genna Brothers: Who Were They?

The Gennas were Sicilian immigrants who settled in Chicago’s Near West Side, a neighbourhood that became the base for their bootlegging empire. During Prohibition they ran a network of home stills operated by Sicilian and Italian immigrant families, paying workers around $15 a day to produce cheap — and often dangerously adulterated — rotgut whiskey. At their peak they were supplying a significant portion of Chicago’s illegal liquor market.

Angelo Genna (Feb 3, 1898 – May 26, 1925) was the main leader of the Genna family and the man who masterminded the assassination of Dean O’Banion in November 1924. He was killed by the North Side Gang in May 1925, shot while driving near his home.

Mike Genna (Jan 18, 1895 – June 13, 1925), known as “The Devil,” was a hot-headed and violent enforcer. He met his death in a police shootout following a car chase through the streets of Chicago, just weeks after his brother Angelo was killed.

Tony Genna (July 12, 1890 – July 8, 1925), known as “The Gentleman,” was something of an anomaly among his brothers — a qualified building contractor and architect with his own legitimate business. His respectability made him no safer. He was lured into an ambush and shot dead by Vincent Drucci and Bugs Moran in July 1925.

James Genna (Jan 18, 1888 – Nov 8, 1931) was one of the three surviving brothers who fled to Italy after the killing spree wiped out Angelo, Mike, and Tony in the space of three months.

Peter Genna (1880 – May 13, 1948) also fled with Sam and James but later returned to Chicago, where he ran a legitimate olive oil importing business for the rest of his life.

Sam Genna (unknown – Dec 20, 1951) was the political fixer for the family — the brother who greased palms and kept officials onside. He was the last of the six brothers to die, surviving some 26 years after the bloody summer of 1925.

The Genna Brothers’ Bootlegging Operation

The foundation of the Genna operation was cheap liquor. While Al Capone and Johnny Torrio were importing higher-quality Canadian whiskey, the Gennas flooded the market with home-produced rotgut. Their Near West Side network employed hundreds of immigrant families who ran small stills in their homes and apartments. The product was rough and often poisonous — deaths from Genna liquor were not uncommon — but it was cheap and it was everywhere.

This strategy made the Gennas enormously profitable but also created serious friction with other Chicago bootleggers, particularly the North Side Gang under Dean O’Banion, who resented both the quality issue and the Gennas encroaching on his territory.

The Murder of Dean O’Banion

The Genna Brothers are best remembered for their role in ending the life of Dean O’Banion, the colourful leader of the North Side Gang who ran his operations out of a flower shop on North State Street.

The breaking point came at a mob sit-down where Angelo Genna had run up a substantial gambling debt with Al Capone. Capone suggested the debt be quietly forgiven as a professional courtesy to the Gennas. O’Banion ignored this completely and called Angelo directly, ordering him to pay in full within seven days. In the world of organised crime, this was a profound insult.

The one man keeping the peace was Mike Merlo, the respected head of the Unione Siciliana. When Merlo died of cancer in November 1924, the restraint died with him. Johnny Torrio gave the order. On November 10, 1924, Frankie Yale and two Genna hitmen — John Scalise and Albert Anselmi — walked into O’Banion’s flower shop and shot him dead.

The Fall of the Genna Brothers

The murder of O’Banion did not go unanswered. The North Side Gang, reorganised under Hymie Weiss and later Bugs Moran, launched a campaign of revenge that tore through the Genna family with devastating speed.

Between May and July 1925, Angelo, Mike, and Tony were all dead. Three brothers killed in three months. James, Peter, and Sam fled to Italy. The Genna organisation collapsed almost overnight, and what remained — including the services of Scalise and Anselmi — was absorbed by the Chicago Outfit.

The O’Banion murder and the war it sparked continued to escalate for years, drawing in more and more of Chicago’s underworld until it culminated in the St. Valentine’s Day Massacre of February 14, 1929 — when Capone’s men gunned down seven members of the Moran gang in a Lincoln Park garage.

Further Reading

• Get Capone by Jonathan Eig — the definitive account of the FBI’s pursuit of Al Capone, covering the full Prohibition-era Chicago underworld.
• Capone: The Life and World of Al Capone by John Kobler — the classic biography, essential reading for this era.
• The St. Valentine’s Day Massacre by William Helmer — traces the full story of the event the Genna brothers helped set in motion.