The Justice System, Jerry Springer, and Jack “Legs” Diamond’s Legacy

The Justice System, Jerry Springer, and Jack “Legs” Diamond’s Legacy

Every moonshiner and bootlegger has a story about how he got started. Most of the time, it’s folks carrying on a family tradition or making a living the only way they know how. Noble reasons or not, bootlegging is an illegal activity, and it can attract the kind of people you don’t dare look at sideways. When it boils down to it, there are two types of outlaws in this world – those who turn to crime because they don’t have any other choice and those who are just plain mean. 

There are a lot of colorful and dangerous characters from the days of Prohibition. One of these was John Diamond, better known as Jack “Legs” Diamond. Legs was a nickname he earned from dancing and chasing women. It’s just as likely that “legs” was a nod at how quick he could outrun anyone after him. Jack was a mean and dangerous fellow whose violent life led to an early grave, but it made him famous in Upstate New York. He was the biggest celebrity there during Prohibition. He was also known by the name Gentleman Jack. Someone back then was just being sarcastic when they came up with that one.

Diamond wasn’t the kind of man you wanted as an enemy, or friend even. He played a part in the Manhattan Bootleg Wars, but headed north when things got too dangerous. Not that it helped much. “Legs” kidnapped and tortured a truck driver in an attempt to find out who supplied the booze the guy was smuggling. It was a bold move that ended up being more trouble than it was worth.

            Just like today, the justice system had more problems than Jerry Springer’s studio audience. Jack “Legs” Diamond was acquitted twice for the kidnapping and torture of the truck driver, but it landed him on law enforcement’s radar. In 1930, he took a trip to Europe to get cured via some mineral water quackery. Well, not really. That’s what he told everybody he was doing while working to find a supply of rye whiskey to smuggle back to the States. As soon as he got off the boat in France, he was arrested and questioned, sent on to Germany, where he was arrested and questioned again. This time he got deported, and sent back via transport to Philadelphia, where he was arrested again. The Judge in Philly let “Legs” go on the condition that he leave town within the hour. Jack complied and went back to New York.

            Sometimes it’s hard to tell whether someone is tough, blessed with dumb luck, or both. Jack “Legs” Diamond survived being shot twice while filling in for his brother as a bodyguard to Jacob Orgen. Later on, Diamond got shot five times in a hotel when he was ambushed in bed. After recovering from that, he was shot gunned three times when walking into a diner. Again he survived, but his Irish luck ran out on December 18th, 1931. “Legs” was gunned down, and no one knows who did it. It could have been rival mobsters, cops tired of seeing him constantly getting away with everything, or even local politicians. The smart money is on the politicians. The local democratic political machine was on a crusade to stamp out any and all corruption, other than its own. Diamond was starting to be too much competition. Party chair Daniel O'Connell more or less admitted it in an interview he gave near the end of his life.

            If there’s one thing to take away from Jack “Legs” Diamond’s life, it’s to never get between a politician, and his money.