Jack Diamond (gangster) - Prohibition & The Manhattan Bootleg Wars

Prohibition & The Manhattan Bootleg Wars

During the late 1920s, Prohibition was in force, and the sale of beer and other alcohol was illegal in the United States. Diamond traveled to Europe to score beer and narcotics, but failed. He did score liquor which was dumped overboard in partially full barrels which floated into Long Island as ships entered New York. He paid the children a nickel for every drum they brought to his trucks.

Following Orgen's death, Diamond went to work overseeing bootleg alcohol sales in downtown Manhattan. That brought him into conflict with Dutch Schultz, who wanted to move beyond his base in Harlem. He also ran into trouble with other gangs in the city. A young man named Stanley Wheeler befriended Diamond and served as his closest friend and driver on many of his quick getaways. Diamond failed to make a payment, and he was shot at the Hotel Monticello by gangsters. He then moved to the Catskills to get away from the threat of Schultz and others. Diamond was shot five times on one occasion when Schultz's men surprised him at a private dinner. With Wheeler driving him, he escaped with bullet holes in his car, and minor bullet wounds.

In 1930, Diamond and two henchmen kidnapped Grover Parks, a local truck driver, and demanded to know what kind of beer or alcohol he was carrying. After he denied that he was carrying anything, they beat and tortured him. They eventually let him go. A few months later, Diamond was charged with the kidnapping of James Duncan. He was sent to Catskill, New York for his first trial, but was acquitted. However, he was convicted on federal case on related charges, and he was sentenced to four years in jail. In a third trial, in Troy, New York, he was acquitted.

In early 1931, Schultz' gunmen fired on Diamond with machine guns at the Aratoga Inn near Cairo, killing two bystanders in the process.

In August of 1931 he and Paul Quattrocchi were on trial for bootlegging.