Joe Bruno's Mobsters - Six Volume Set (7 page)

Diamond was released from prison in 1921, and he decided that New York City was the place he could make his fortune. Diamond and his brother Eddie relocated to Manhattan's Lower East Side, where they fell in with an up-and-coming gangster named Lucky Luciano. Diamond did various odd jobs for Luciano, including a little bootlegging, in conjunction with Brooklyn thug Vannie Higgins. Diamond's marriage to Florence Williams lasted only a few months (he was never home). However, Diamond's luck changed when Luciano introduced Diamond to Arnold “The Brain” Rothstein, a notorious gambler and known financial wizard. This was the break Diamond was waiting for, and he made the most of it.

After starting out as a bodyguard for Rothstein, Rothstein brought Diamond in as a partner in his lucrative heroin business. When his pockets were full with enough cash and his need for Rothstein diminished, Diamond, in concert with his brother Eddie, decided to branch out on their own.

The Diamond Brothers figured they could make a bundle, hijacking the bootlegging trucks of other mobsters, including those of Owney Madden and Big Bill Dwyer. This was not a very good idea, since Madden and Dwyer were part of a bigger syndicate of criminals that included Luciano, Dutch Schultz, and Meyer Lansky. In no time, Diamond was persona-non-grata in the gangster world and free pickings for anyone who wanted to get rid of him.

In October 1924, Diamond was driving a Dodge sedan up Fifth Avenue, when at 100
th
Street a black limo pulled up alongside him. A shotgun was fired at Diamond from the back window of the limo, but Diamond was too quick to be killed. He ducked down and hit the accelerator, without looking where he was going.

Miraculously, Diamond was able to escape his shooters and drive himself to the nearby Mount Sinai Hospital. The doctors removed pellets in his head, face, and feet, and when the cops arrived to question him, Diamond dummied up.

“I dunno a thing about it,” Diamond told the fuzz. “Why would anyone want to shoot me? They must of got the wrong guy.”

Soon, Diamond became friends with a gangster not looking to kill him. His name was “Little Augie” Orgen. Orgen installed Diamond as his chief bodyguard. In return, Orgen gave Diamond a nice share of his bootlegging and narcotics businesses. This friendship went just fine, until October 15, 1927, when Louis “Lepke” Buchalter and Gurrah Shapiro gunned down Orgen on the corner of Norfolk and Delancey Street, with Diamond supposedly standing guard over Orgen.

Diamond was shot in the arms and legs (probably by accident), necessitating another trip to the hospital. Upon his release, Diamond made nice with Lepke and Shapiro, and as a result, the two killers gave Diamond Orgen's bootlegging and narcotics businesses as a reward for being stupid enough to get in the way of bullets meant for Orgen.

Now, Diamond was on top of the world. He had plenty of cash to throw around, and he became a mainstay in all of New York City's top nightclubs, usually with showgirl Kiki Roberts on his arm (despite the fact he was still married to his second wife Alice Kenny). Diamond was seen regularly at the Cotton Club, El Fay, and the Stork Club, and his picture was frequently in the newspapers, which portrayed Diamond not as a gangster, but as a handsome man-about-town.

Soon, Diamond was part owner of the Hotsy Totsy Club, located on Broadway between 54
th
and 55
th
Street, with Hymie Cohen as his fronting partner. The Hotsy Totsy Club had a back room where Diamond frequently settled business disputes, usually by shooting his adversaries to death, then carrying them out as if they were drunk.

Diamond's downfall started on July 13, 1929, when three unruly dockworkers got loaded and started a ruckus at the
Hotsy Totsy Club's bar. Diamond jumped in, with his gang member Charles Entratta, to stop Diamond's manager from being throttled.

“I'm Jack Diamond and I run this place,” Diamond told the dock workers. “If you don't calm down, I'll blow your (expletive) heads off.”

The talking didn't work and soon the shooting started. When the smoke cleared, two dockworkers were dead and the third one was injured. As a result, Diamond and Entratta took it on the lam.

While they were in hiding, Diamond decided that before he could go back to doing what he was doing before, the bartender and three witnesses had to be killed. And soon they were, Cohen turned up dead, too, and the hat check girl, the cashier, and one waiter disappeared from the face of the earth.

Diamond and Entratta, with everyone out of the way who could possibly harm them, calmly turned themselves into the police and said, “I heard we were wanted for questioning.”

No charges were ever brought against Diamond and
Entratta for the Hotsy Totsy Club murders, but Diamond realized New York City was no longer safe for him. As a result, Diamond closed the Hotsy Totsy Club, and he relocated to Greene County in upstate New York.

From upstate New York, Diamond ran a little bootlegging operation. However, after a few months of impatience, Diamond sent word back to gangsters in New York City, namely Dutch Schultz and Owney Madden (who had scooped up Diamond's rackets in his absence), that he was coming back to take back what was rightfully his. This put a target in the middle of Diamond's back, and he soon became known as the “clay pigeon of the underworld.”

Diamond was sitting at the bar of the Aratoga Inn, near Arca, New York, when three men, dressed as duck hunters, barreled into the bar and filled Diamond with lead. The doctors gave him little chance for survival, but four weeks later, Diamond walked out of the hospital and told the press, “Well, I made it again. Nobody can kill Jack 'Legs' Diamond.”

A few months later, as Diamond was leaving an upstate roadside inn, he was shot four times: in the back, leg, lung, and liver. Yet again, Diamond beat the odds the doctors gave him, and he survived.

In December 1931, Diamond was not so lucky, when after a night of heavy drinking at the Kenmore Hotel in Albany, Diamond staggered back drunk to his nearby boarding room and fell asleep. The landlady said afterwards, that she heard Diamond pleading for his life, then she heard three shots. Apparently two gunmen had burst into Diamond's room, and while one held him by his two ears, the other put three slugs into his brain.

The killers escaped in a red Packard, putting an end to the myth that Jack “Legs” Diamond was the “gangster who couldn't be killed.”

E
astman, Monk

Monk Eastman was born Edward Osterman, in 1875, in the Williamsburg section of Brooklyn.  Edward's father owned a restaurant, and to keep the young Osterman busy, his father bought him a pet shop.
Osterman's business venture failed, reportedly because he kept fighting with customers who wanted to purchase pets he became especially fond of. Out of business, young Osterman relocated to lower Manhattan, and to make money, he dived headfirst into a life of crime. He operated under several aliases, before finally settling on the last name of Eastman.

The short and stocky Eastman was nicknamed “Monk,” because he resembled a monkey stalking the streets. He had an unkempt appearance, and his pumpkin-sized head and frazzled hair were covered by a derby two sizes too small. Eastman became known as a feared brawler, and he was the bouncer at one of the roughest nightclubs on the Lower East Side, the New Irving Social Club on the Bowery.

While he patrolled the club keeping the peace, Eastman carried a four-foot stick, which he used to crack the heads of any patron who was not behaving properly. In just a few short months, Eastman had whacked the heads of 49 near-do-wells, and not liking crooked numbers, he conked the skull of an innocent man just to make it an even 50. Eastman sent so many people to Bellevue Hospital, the hospital staff jokingly called their emergency room, “The Eastman Pavilion.”

Yet Eastman apparently had a soft spot for women. If anyone of the female persuasion needed to be reckoned with, he reportedly dropped his stick, took off his brass knuckles, and hit the woman just hard enough to give her a black eye. No hospital visit was necessary for the lucky young lady.

Eastman also was a willing killer; for hire, or for just plain fun, especially when he was drunk, which was often. Eastman believed in “Dead Man's Eyes,” which is the concept that when a person dies, the last thing that person he sees is permanently imprinted on the retina of their eyes. When Eastman killed someone, he truly believed he was leaving proof on the victim's eyes that he was the killer. So Eastman, being the cautious bloke that he was, after he shot someone dead, not to leave any incriminating evidence, he shot out his victim's eyes out, too.

Eastman assembled a rough and tumble gang that reportedly numbered close to 2,000, mostly Jewish men. Eastman curried favor with politicians by doing them “little favors,” like patrolling polling places during elections, to make sure each voter cast their vote for the proper man. The politicians returned the favor by springing Eastman out of jail, whenever an ambitious policeman decided to do something foolish, like actually arresting Eastman for one of his many crimes. However, Eastman was so out-of-control with his thievery, thuggery, and killings, he soon ran out of political favors.

In 1904, Eastman was finally sent to prison for robbing and beating a man uptown. He was sentenced to 10 years at Sing Sing Prison, but he was released after serving only five.

When Eastman got back to his old hunting grounds, he discovered his gang had been dismantled, and his former men were now working for other scattered ringleaders. Eastman was reduced to performing petty crimes in the streets for a while, until he had the bright idea of joining the army. Eastman wound up serving in World War I, in France, with the 106th Infantry Regiment of the 27th Infantry Division. Eastman was honorably discharged in 1919, and he immediately went back to the streets of the Lower East Side, causing his usual mayhem.

Eastman soon became involved with a crooked Prohibition agent named Jerry Bohan. On the night of December 26, 1920, the two men got into a drunken argument, and Bohan, knowing full well about Eastman's reputation for killing easy, shot Eastman dead, in front of 62 East 14
th
Street.

F
ein, Benjamin “Dopey”

Benjamin “Dopey” Fein was born on the Lower East Side of Manhattan in 1889. He was nicknamed “Dopey” because an eye condition made his eyelids droop, and he seemed either to be falling asleep, or under the influence of a narcotic: in the street vernacular, “dope.”

Fein dropped out of school at an early age, and he became involved is various street crimes, like pickpocketing and petty robberies. Fein enlisted groups of youngsters, particularly from the school he dropped out of (PS 20 on Essex Street), and soon he had scores of preteen criminals terrorizing the streets of the Lower East Side.

In 1905, Fein's luck turned sour, when he was arrested for assault and robbery, and sent upstate to the Elmira State Penitentiary, where he cooled his heels for three years. Fein was released and arrested twice more, before he finally hit the streets in 1910 and joined “Big” Jack Zelig's notorious gang.

After Zelig was murdered in 1912, Fein embarked on an upwardly horizontal career move. Fein started working for the bosses of several labor unions, especially the Garment Workers Union (GWU). Fein and his men became “schlammers,” which meant they broke the heads of any union members who did not toe the line the union bigwigs had laid out for them.

After the Triangle Shirtwaist Factory Fire in 1911 (which killed 146 people, 123 of them women), Fein became involved with the ILGWU: the International Ladies Garment Workers Union. Fein had a reputation of making sure the woman in his union got paid the exact same salary for their work as did the men in the GWU, which was contrary to the common practice at the time.

Being on the ladies' side was a Machiavellian maneuver, which allowed Fein to use these ILGWU women as “toters,” or carriers of concealed weapons, to which Fein and his gang had ready access whenever needed. Fein's female accomplices hid guns, knives, and brass knuckles, in mufflers, or in their hair puffed up high on their heads, in a unique hairdo called the “Mikado Tuck-up.”

Fein's main foe at the time was Jack
Sirroco. Sirroco was also heavily involved in the labor movement; not with the unions, but rather with the manufacturers, which put him at cross purposes with Fein. Fein and Sirroco's gangs fought numerous battles, especially when both sides showed up representing opposing parties at a labor strike.

In January 1914, Fein and his gang ambushed
Sirroco's gang at a party at Arlington Hall, on St. Mark's Place. Only one person was killed, and it turned out to be an innocent bystander named Fredrick Strauss, who just happened to be a County Clerk officer. This put another nail in Fein's quickly closing coffin.

The final nail was inserted in the fall of 1914, when Fein threatened to kill B.
Zalamanowitz, an official from the butchers union, who refused to pay Fein $600 to protect his striking butchers.  Zalamanowitz, knowing Fein's murderous reputation, ran frightened to the police. On Fein's next meeting with Zalamanowitz, hidden cops watched as Fein repeated his intentions to harm Zalamanowitz if he did not pay up right away. The police arrested Fein on the spot; on first-degree extortion charges.

After a few days in the slammer, Fein, realizing his union influence was on the wane, decided to become a canary for the cops. Unknown to his associates in the labor unions, Fein had kept meticulous records on all his “labor transactions.” He had written down everything, including who was involved in what, when, where, and how. This led to the arrest and convictions of dozens of people, including high-ranking officials of the Garment Workers Union and the International Ladies Garment Workers Union.