Jack "Legs" DiamondLegs has what is perhaps the most notorious reputation for not dying in the history of organized crime. Over the course of his career, which spanned from 1919 to 1931, he survived at least 17 bullets. In 1930, Dutch Schultz, Legs' primary rival, was heard to ask "Ain't there nobody what can shoot this guy so he don't bounce back?!"
Legs was the front man for Arnold Rothstein. Rothstein paid for much of Legs' bootlegging operations. When Rothstein died, Legs began to lose his grip as the Dutchman expanded his bootlegging and gambling operations into downtown Manhattan. Eventually, Legs and Dutch lost this turf to the real mafia, which grew out of the failed reign of Salvatore Maranzano.
Accidental HeroIn 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, they put Legs on the job. While Legs was definitely a criminal, he tended to avoid murder. He hired a dim-witted associate to off Kaplan, and after a considerable number of failed attempts, Kid Dropper was eventually dropped.
Legs became famous in the underground world, and with the heavy turnover of the bootlegging world, he rose to power with the help of Little Augie. Legs quickly snagged a wife, an ugly little lady named Alice who played the part of the devoted spouse, but secretly hated his guts.
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. Augie refused, and was gunned down while trying to get into a cab. Augie's wunder-kine bodyguard was right beside him, and caught 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 hooch sales. In 1927, Dutch Schultz finally rid himself of Vincent Coll, and felt that he could easily expand his operations beyond Harlem.
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. But when Rothstein died on November 6th, 1928,Legs' bank roll dried up.
TwiceDutch lost a lot of men trying to kill the Diamond brothers. Legs hid in small apartments around Manhattan, while his brother Eddie, who was sick with tuberculosis, stayed in Denver. When Schultz's men found Eddie in the mile-high city, they pumped over 100 rounds into his car. But Eddie had the same dumb luck as his brother, and survived the attack, only to succumb to his respiratory ailments.
Legs always cheated on Alice on Alice. In 1929, Schultz's men tripped across Legs in a suite at the Monticello hotel having diner with his favorite lover, a dancer named 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.
Three Times a TargetIn 1931, Legs moved his headquarters north to Acra, New York, but again Schutlz's men found him. This time, in true American style, they attempted a drive-by shooting. Legs was caught standing out for some air in front of his hotel room. He was only hit by three bullets, but two other patrons of the hotel died of tommy gun wounds.
Four on the FloorLater 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. 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 two shots into his brain. On the way out, one of the gunmen returned to fire one last shot into Legs' head, saying "This guy ain't human!"
But it wasn't needed. Legs was already dead. It took four years to kill Legs. His killers were never found, but upon identifying the body, Alice Diamond's first words to detectives were "I didn't do it."