Jack "Legs" Diamond

He was always getting caught in a stream of bullets that were intended for the guy he was being paid to guard. Thus, as a bodyguard, Legs was also a dismal failure. He did a brief stint as a bodyguard for Arnold Rothstein in 1928; he spent no more than a month on the job. Yet he still managed to get his boss shot, and to catch a couple rounds himself in the process.

Accidental Hero

Legs never really intended to become a beer baron. He just lucked into it. His main talent as a leader was his not-dying: because no one could bump him off, Legs couldn't lose control of his outfits. It's said that Rothstein paid for much of his empire's upkeep; and when Rothstein was killed, Legs' team of talented goons mostly defected to Dutch Schultz's side.

In 1923, Jacob "Little Augie" Orgen was having trouble with a bootlegger named Nathan 'Kid Dropper" Kaplan. Kid Dropper was hard to find, and Orgen decided to call in outside help from a local gang of kids called the Hudson Dusters. Legs had joined the Dusters just before World War I broke out, but he'd been thrown in jail in 1918 when he refused to ship out for Europe after being drafted. When he got out in 1919, he became the Dusters' most prolific criminal.

So when Little Augie came to the Dusters in 1923, he immediately put Legs on the job. While Legs was definitely a criminal, he was not much of a killer. He hired a dim-witted associate to off Kaplan, and after a considerable number of failed attempts, Kid Dropper was dropped like a bag of potatoes.

Augie gave Diamond a shitload of bootlegging territory after this success. Thus began Legs' love affair with gaudy clothes, fast women, and hot-footed dancing. Somewhere around this time, Legs grabbed a wife, an ugly little lady named Alice who played the part of the devoted spouse.

Shot One

As the heady days of the early 20's began to give way to the bloody days of the early 30's, Legs became Augie's personal bodyguard. Unfortunately, when Louis Buchalter showed up on Augie's doorstep asking for rights to run the garment district, Legs was unable to save his boss. When Augie refused, he was gunned down while trying to get into a cab. Of course, his wunder-kine bodyguard was right beside him, and caught his two bullets as a prize for failing to protect his boss.

With Augie dead, Legs made peace with Buchalter and remained the controller of much of downtown Manhattan's bootlegging. But by 1927, Dutch Schultz felt that he could easily take over this turf. Having disposed of Vincent Coll, the Harlem beer baron felt that he was ready to expand, and Legs had the most delicious looking turf in the city.

Legs held off the inevitable, until late 1928 when his empire began to crumble. Between Schultz's constant attacks and the ever growing Castellamarese wars between Salvatore Maranzano and Joe Masseria, New York was beginning to run out of shaved gorillas to do the dirty work. Both Schultz and Diamond were running out of men and money as a result of the burgeoning prohibition combat.

Dutch lost a lot of men just trying to kill Legs and his brother Eddie. Legs was always well hidden, and his brother Eddie stayed in Denver, sick with Tuberculosis. When Schultz's men found Eddie in the mile-high city, they pumped over 100 rounds into his car. Eddie had the same dumb luck as his brother, and survived the attack.

Shot Twice

By 1929, Legs was cheating on Alice. Schultz's men tripped across Legs in a suite at the Monticello hotel having diner with his favorite lover, Kiki Roberts. They opened fire on the pair. Roberts got away intact, but Legs caught five bullets and spent a few weeks in the hospital, his wife sitting loyally at his side, playing the part of the cunthold.

Three Times a Hades

In 1931, Legs moved his operations north to Acra, New York, but again Schutlz's men found him. This time, they tried a drive-by. Legs was caught standing out for some air in front of his hotel room by a carload of three gorillas. But he was only hit by three bullets. His neighbors weren't so lucky, and two other patrons of the hotel died of Tommy Gun wounds.

Four on the Floor

Later that same year, Legs went out drinking with his wife and some friends. At around ten, he excused himself and headed over to Kiki Roberts' house. There, he got drunk on both silly sauce and on vagina cocktails. He then took a cab to a hideout in downtown Manhattan. When he'd passed out on the bed inside, two gunmen walked into his room. They picked him up, stood him against the wall and pumped three shots into his brain. On the way out, one of the gunmen wanted to go back and finish the job stating that "This guy ain't human!"

But it wasn't needed. Legs was finally dead. It took four years and 17 bullets to kill Legs. The newspapers dubbed him "The Clay Pigeon of the Underworld." His killers were never found.