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The Imprecision Of “Stopping Power” The Unkillable Jack Diamond Written By Will Dabbs, MD

Jack “Legs” Diamond was an old-school thug.
He came from the factory broken. Photo: Public Domain

Just what is “stopping power” anyway? One dude strolled nonchalantly into the ER when I was on duty, having taken a 9mm ball round to the pelvis. He was only minimally inconvenienced. Another guy sped away from a drug deal gone bad with the unlicensed pharmacist throwing 9mm rounds his way with vigorous dispatch.

Then he got home and noticed blood. A 115-grain FMJ round had punched through the trunk, back seat and then front seat before embedding in his back fat. This gentleman legitimately did not know he was shot. And then there was the sweet little old lady who caught a .25 ACP round to the neck during a robbery and will spend the rest of her days in a motorized wheelchair. How well bullets perform in the real world is bizarrely unpredictable. And then there was this guy.

The 1921 Colt Thompson got all the press. However, then,
as now, it was the humble handgun that spilled the most blood.

Origin Story

Nobody is really sure what Jack “Legs” Diamond’s real name was. He went by John Thomas Diamond, as well as John Nolan, John Moran and Gentleman Jack. He was born in the summer of 1897 to Sara and John Moran. It was obvious from the outset this little kid just wasn’t right.

Part of that was likely his sordid environment. Jack’s mom, Sara, was frail by nature and died of an illness when Jack was 16. Jack joined a Manhattan criminal gang called the Hudson Dusters soon thereafter. He was first arrested for burglary a year after his mom’s death.

Diamond enlisted in the Army intending to fight in Europe during World War I but lost his enthusiasm in short order. He deserted, was caught and served several years in Leavenworth.

Prison is grad school for criminals. When Diamond was finally released, he was free to pursue his true calling. In 1921, he entered the employ of a professional criminal named Arnold Rothstein. Diamond’s job description included bodyguard and general thuggery.

Jack Diamond’s nickname “Legs” spawned from one of two possible sources. He was purported to be a fairly competent dancer. He also established a well-earned reputation for being able to expeditiously get out of trouble. Somewhere along the way, his associates began calling him “Legs,” and the moniker stuck.

Being a mob enforcer doesn’t have the greatest retirement plan. Additionally, Jack Diamond was a hyperactive lad and a serial womanizer. Despite being married, he carried on a protracted illicit relationship with a prominent New York showgirl named Marion “Kiki” Roberts.

These suboptimal personal habits and the curiously violent nature of his profession synergistically combined to keep Jack Diamond’s physicians gainfully employed. By 1931, Diamond was known as the “Clay Pigeon of the Underworld.”

Normal people don’t have a nemesis. Jack Diamond, however, was not a normal person. His criminal counterpart was the infamous mobster Dutch Schultz. When describing Diamond, Schultz once remarked to his merry mob of misfits, “Ain’t there nobody that can shoot this guy so he don’t bounce back?”

Gangsters used a variety of handguns during the liquor wars of the 1920s. From left to right, we have the Colt Model 1903 .38 revolver, the .45 ACP Colt M1911 pistol, the 9mm P08 Parabellum
and the .32 ACP Colt Model 1903.

A Curiously Hazardous Profession

Prohibition ran from 1920 until 1933. The stock market crash that accompanied the Great Depression kicked off in 1929. The toxic combination of these two events meant there was a great deal of money to be made for those willing to ignore the law.

Diamond saw this as an opportunity and traveled to Europe in search of alcohol and drugs. He returned with barrels of liquor that he had dumped into New York Harbor. Partially filled, these barrels floated low in the water. By studying the tides, Diamond could predict where they might make landfall. He paid local children a nickel apiece to retrieve these containers.

Diamond was the partial owner of the Hotsy Totsy Club on Broadway. With a name like Hotsy Totsy Club, they weren’t hosting Sunday School brunches or teaching underprivileged blind kids to read.

Diamond used his club as a home base for all manner of illicit activities. In July of 1929, Diamond and an associate named Charles Entratta broke up a fight in the club by shooting three of the participants.

Two of the inebriated thugs, Simon Walker and William Cassidy, died as a result. William’s brother, Peter, was badly wounded. In response, the three men’s criminal associates kidnapped the Hotsy Totsy’s bartender, three members of the waitstaff and the cute hatcheck girl. One of the five was later found murdered in neighboring New Jersey. The other four were never heard from again.

There followed arrests for kidnapping, assault and sundry other crimes. Diamond attempted to flee to Europe but was unwelcome in the UK, Belgium and France. Eventually, German police deported him back to Philadelphia.

The first time Jack Diamond was shot, it was with a 12-bore shotgun. This vintage Remington Model 11 is typical of the genre.

A Notoriously Hard Man to Kill

Jack Diamond was the target of at least five assassination attempts. The first occurred in 1924 while he was attempting to hijack a truck full of liquor belonging to a rival criminal gang. Diamond caught a charge of 12-gauge shot to the face and head but recovered.

Three years later, Diamond was pulling bodyguard duty for a proper villain named Jacob “Little Augie” Orgen. While the two men were walking in Manhattan’s Lower East Side, they were confronted by a trio of assailants.

These three shooters opened fire at close range, killing Orgen outright and hitting Diamond twice in the chest. Both rounds passed beneath the gangster’s heart, and he recovered after a protracted hospital stay. Though he undoubtedly knew the men who shot him and killed his boss, Diamond refused to reveal their identities to police. Jack Diamond was a lot of things, but he wasn’t a snitch.

In October of 1930, Diamond was a guest at the Hotel Monticello on Manhattan’s West Side. Three assassins forced their way into his room and shot him five times. The shooters then fled. Diamond, for his part, stopped long enough to drink two shots of whiskey before staggering into the hallway in his pajamas where he collapsed. After two and a half months in the hospital, Legs Diamond was released to sow yet more chaos.

In 1930, Diamond and a pair of thugs kidnapped and beat a truck driver named Grover Parks, who was carrying a load of hard cider for a rival gang. Even if the victim is a thug himself, it was still against the law to beat people within an inch of their lives. In April of 1931, Diamond was arrested for Parks’ assault. Two days after his arrest, Diamond was released on a $25,000 bond.

Five days after that, Diamond was a guest at the Aratoga Inn, a roadhouse near Cairo, NY. After taking a meal with three associates in the roadhouse restaurant, Diamond stepped outside to get some air. Gunmen masquerading as duck hunters opened fire from a parked car and shot him three times at close range. Bystanders drove the bleeding Diamond to the hospital, where he recovered yet again after a protracted stay. By now, he was likely growing weary of hospital food.

Jack Diamond’s weapon of choice was a 4″ P08 Parabellum pistol equipped with the 32-round snail-drum magazine from an Artillery Luger.

Nobody is Immortal

If you’re counting, by then, Legs Diamond had been shot with 10 handgun rounds and an unknown number of shotgun pellets. The rock-hard mobster seemed unkillable. However, on December 18, 1931, Jack Diamond’s luck ran out.

By now, Diamond was staying at a rooming house in Albany, NY. He took dinner out with friends at a local restaurant before partying the night away with his mistress, Kiki Roberts. Come the dawn, Diamond staggered back to his boarding house and passed out on his bed.

Two attackers entered his room soon thereafter with a key. One man held him in place while the other pumped three rounds into the back of his head. The two gunmen fled, but one had second thoughts, ran back to the room and shot him several more times.

Mrs. Laura Woods, Diamond’s landlady, later testified that she heard one of the shooters say, “Oh, hell, that’s enough. Come on.” His killers were never caught.

There was ample conjecture. Some suspected local mafia hit men. Others postulated that the shooters had been crooked members of the Albany police force. Regardless, Legs Diamond was finally well and truly dead.

Legs Diamond was buried at Mount Olivet Cemetery in Maspeth, Queens, NY. Though there was no formal service, there were around 200 people who attended just to gawk.

Two years later, the body of Legs Diamond’s widow, Alice Kenny Diamond, was discovered shot to death in her apartment. Mob watchers suspected she was murdered to keep her from telling what she knew about her husband’s nefarious dealings.

This is the SS Belgenland. In 1930, Jack Diamond took this ship to Europe in search of illicit booze and drugs during Prohibition. Photo: Public Domain

The 9mm P08 Parabellum and the Colt M1911 .45 were both powerful and concealable gangster weapons used during the Roaring ’20s.

Ruminations

Legs Diamond was a killer. His weapon of choice was a German P-08 Parabellum pistol with a 4″ barrel and a 32-round snail-drum magazine. In the years following the First World War, such martial firearms would have been relatively commonplace, having been brought back from Doughboys serving overseas.

The 9mm round was appealing then for the same reasons it is appealing now. A drum-equipped Luger pistol was sort of concealable and offered unparalleled firepower.

So, what are the tactical lessons to be learned from the sordid life and gory death of Jack Diamond? For starters, handguns can be pretty substandard manstoppers, particularly firing ball ammo.

They will certainly do the job, but shot placement and ammunition selection are critical. In a social exchange of gunfire, most any rifle is more effective than most any pistol. At appropriate ranges, most any shotgun is more effective than most any rifle. It finally took 16 pistol rounds and Lord only knows how many shotgun pellets to put Jack Diamond down.

Jack Diamond shuffled off this mortal coil in 1931 at age 34. By the time he finally expired in a pool of his own blood, Legs had seen and done an awful lot of bad things. However, even nearly a century later, he can still teach us a great deal about the art of armed combat.

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