SYNDICATEEMPIRE OF VICE

A ruthless Sicilian Mafia boss who demanded loyalty, respect, and a share of the profits, Giuseppe Masseria ruled through intimidation and violence. His criminal empire encompassed extortion, protection rackets, gambling, and bootlegging. After surviving an assassination attempt that left bullet holes in his hat, he earned a reputation as a man who could dodge bullets. An ambitious figure of the Mafia’s old guard, Masseria sought to bring New York’s competing Italian gangs under his authority.

A gambler, financier, and criminal mastermind, Arnold Rothstein treated organised crime like a business. Infamous for his alleged role in fixing the 1919 World Series, he built his fortune through gambling, loan sharking, bootlegging, and narcotics. More importantly, he became a mentor to the next generation of organised crime, influencing future legends such as Lucky Luciano, Meyer Lansky, and Frank Costello. For Rothstein, intelligence and connections were worth more than brute force.

From humble beginnings as a dockworker, William Dwyer rose to become one of New York’s wealthiest bootleggers, building a vast liquor-smuggling operation through waterfront connections and police corruption. His ambitions extended beyond the underworld into professional sports, where he used his fortune to purchase the New York Americans hockey team and acquire interests in other franchises. From the docks to Madison Square Garden, Dwyer found opportunities wherever money could be made.

A mysterious figure of the Roaring Twenties, Max von Gerlach cultivated an image of wealth, sophistication, and extravagant living. Associated with the bootlegging world and fashionable New York society, he is considered a possible inspiration for F. Scott Fitzgerald’s The Great Gatsby, even sharing the character’s famous expression, “old sport.” With his elusive background and carefully constructed persona, Gerlach embodied an era in which fortunes were questionable and appearances were everything.

Born in the Danish West Indies, Casper Holstein became one of Harlem’s wealthiest and most influential figures through the numbers racket, an illegal lottery that flourished throughout the neighbourhood. Yet behind his gambling empire stood a celebrated philanthropist who supported Black colleges, Caribbean communities, and the artists and writers of the Harlem Renaissance. His immense wealth also made him a target, culminating in a sensational kidnapping in 1928. To some, he was a criminal kingpin; to others, a community benefactor.

Born Li Quong Yong, Charley Boston rose to prominence as a founder of the influential On Leong Tong and an unofficial leader of Manhattan’s Chinatown. A merchant and importer with interests in tea shops, he was also convicted of involvement in an opium-smuggling operation. His influence extended beyond illicit commerce: he negotiated peace between rival tongs and developed valuable relationships with local authorities. Such was his standing that even rival factions set aside their differences to honour him after his death.