"THE CLAY PIGEON OF THE UNDERWORLD"

The Murder of Jack “Legs” Diamond

On December 18, 1931, gangster and bootlegger, Jack “Legs” Diamond, was shot to death in a rooming house in Albany, New York. Diamond had already survived five attempts on his life between 1916 and 1931, causing him to be known as the “clay pigeon of the underworld.” In 1930, Dutch Schultz, an enemy of Diamond, remarked to his gang, “Ain’t there nobody that can shoot this guy so that he don’t bounce back?”

This time, Diamond didn’t “bounce back.”

Jack “Legs” Diamond

Diamond, whose real name was John Moran, was born in Philadelphia on July 10, 1897. His parents, John and Sara, were Irish immigrants. In 1889, a younger brother, Eddie, was born. The two boys struggled through grade school, while their mother suffered from health problems. She died on December 24, 1913, and their father moved them to Brooklyn soon after. Jack almost immediately fell in with some of the young street gangs of the era, notably the Boiler Gang. His first arrest for burglary occurred when he broke into a jewelry store on February 4, 1914. More than a dozen arrests would eventually follow. After a brief stint in a juvenile reformatory, he was drafted into the military during World War I. Not surprisingly, he deserted after less than a year and was sent to Leavenworth.

When he got out of prison in 1921, he returned to New York, where he began associating with Charles “Lucky” Luciano, who was then a young, but up and coming gangster. Diamond did odd jobs for Luciano, who introduced him to gambler Arnold Rothstein, who was the most powerful mobster in the city at the time. He eventually became Rothstein’s personal bodyguard and was cut in on the new heroin racket, which was making a lot of money.

Diamond, who had taken in his younger brother Eddie, was now making a lot of cash and the brothers decided to start their own bootlegging business. It was a common practice at the time to hijack liquor shipments from other gangsters and then sell it, hurting the competition and making a huge profit. Unfortunately, the brothers decided to hijack truckloads that belonged to Owen “The Killer” Madden and “Big Bill” Dwyer, two of the most ruthless Irish mobsters in the city. They were also connected to a larger syndicate that was run by Dutch Schultz, Luciano, Meyer Lansky, and others. Once word got around that the hijackings had been carried out by the Diamonds, the brothers lost any protection that they might have had and became targets for everyone.

On October 24, 1924, Diamond was driving his Dodge sedan along Fifth Avenue and stopped at the intersection with 110th Street. A large black limousine pulled up next to him. A shotgun appeared from the back window and, according to witnesses, opened fire on Diamond. He ducked down and hit the gas. He drove an entire block without looking over the dashboard. When he did, he saw that the black car was gone. He drove himself to nearby Mount Sinai Hospital, where doctors removed shotgun pellets from his head and face. When the police questioned him, he shrugged the whole thing off. They must’ve thought he was someone else, he told them.

It was obvious to Diamond that he needed protection, so he turned to Jacob “Little Augie” Orgen, a Jewish gangster who ran several rackets in Lower Manhattan. The main thing that he had going for him, as far as Diamond was concerned, was that he was one of the few people who didn’t want to kill him. Orgen wanted to increase his own power base so that he could compete with Luciano, Lansky, and the rest. Diamond would provide some of the muscle that he needed. Jack and Eddie became Orgen’s bodyguards and, in turn, Orgen cut them in on his liquor and narcotic rackets.

Then, on October 15, 1925, Orgen and Diamond were finishing their daily meetings and collections rounds and were approaching the corner of Delancy and Norfolk Streets in Lower Manhattan. Three men approached them and started shooting. Orgen was fatally wounded in the head and Diamond was hit twice on the right side. He was taken to Bellevue Hospital for emergency surgery and eventually recovered. He refused to tell the police anything and they tried to charge him with murder, but couldn’t make anything stick. Orgen’s murder was never solved, although it was believed to have been arranged by Louis “Lepke” Buchalter and his partner, Jacob “Gurrah” Shapiro. They wanted to take over Orgen’s rackets and it’s believed that Diamond may have been in on the plot. After he was released from the hospital, he took over Orgen’s liquor operation, while Buchalter and Shapiro took over the dead man’s narcotics and other rackets.

With cash now pouring in, Diamond became a regular on the nightclub circuit and his picture started showing up in the newspapers. He was never portrayed as a gangster, though, only as a “wealthy man about town.” The public loved him and so did the ladies. Although married, he was a womanizer and his best-known mistress was showgirl and dancer Marion “Kiki” Roberts. His flamboyant lifestyle kept him out at the clubs at night and this may have been how he obtained the nickname “Legs.” He was a great dancer and was part owner of the Hotsy Totsy Club, a dance spot on Broadway. So, the nickname could have come from this or, as others have suggested, from his uncanny ability to escape death.

On July 14, 1929, violence came to the Hotsy Totsy Club. Two brothers, Pete and William “Red” Cassidy, along with a friend named Simon Walker, started a fight at the club after bartenders and staff members refused to serve the already drunk men. When a waiter told them to quiet down, Red turned on the waiter and began arguing with him. Walker grabbed club manager Hymie Cohen by the arm, demanded service, and threatened to destroy the club if they didn’t get it. He then shoved Cohen to the floor. Diamond and one of his cronies, Charles Entratta, saw the exchanged and stepped in. He told Walker, “I’m Jack Diamond and I run this place. If you don’t calm down, I’ll blow your fucking head off.”

Walker turned to Diamond and snarled, “You can’t push me around.” Those turned out to be his final words.

Diamond and Entratta both pulled their guns and shot Walker and the Cassidy brothers. Red was hit three times in the head, once in the stomach, and once in the groin. Walker was hit six times in the stomach. Both men were dead when they hit the floor. When the police arrived, Pete Cassidy was lying at the bottom of a flight of stairs with three gunshot wounds. Guns were found on all three of the men, who had extensive arrest records.

There were more than 50 people in the club when the incident took place – but no one saw a thing. Their backs were turned, they told detectives, or they were in the bathroom. Within six weeks of the shooting, Cohen, the waiter, two bartenders, and the club’s hat-check girl all disappeared. The waiter’s bullet-ridden body was later found in New Jersey. No trace was ever located of the others.

No witnesses ever came forward, so Diamond and Entratta were never charged. With the heat on him, though, Diamond closed down the club and moved to Greene County in upstate New York with his long-suffering wife, Alice. But he was only in Greene County for a short time before he sent word to New York that he was planning to return soon and reclaim what was his. When he had left the city, Schultz and Madden had quickly taken over his rackets. His planned return made him an immediate target and earned him the moniker of “clay pigeon of the underworld.”

Diamond with his wife, Alice.

In 1930, while preparing for his move back to the city, but also while establishing a bootlegging operation in Greene County, Diamond and two others kidnapped Grover Parks, a truck driver, who had been hauling liquor. They wanted to know where he was picking up his alcohol shipments, but Parks refused to tell them. Oddly, they set him loose. A few months later, Diamond tried the same thing with another driver, James Parks, and this time, he was arrested and charged with kidnapping. He was later acquitted at trial.

In late August 1930, Diamond traveled to Europe. He told reporters that he was on his way to Vichy, France, where he would take a mineral water “cure” for his health. The real reason for the trip, though, was to establish a German liquor source. He was planning to smuggle alcohol from Europe to reestablish his New York operation.

But nothing went according to plan. When the ship docked in Belgium, he was taken into custody by the police. After several hours of questioning, he was put on a train to Germany. When he arrived there, he was arrested by the German Secret Service and put him on a freighter that was bound for Philadelphia. It arrived on September 23 and he was immediately arrested by the Philadelphia police. At a court hearing on the same day, Diamond was told that he would be released if he left for New York within the hour. The weary gangster readily agreed.  

In New York, he moved into the Hotel Monticello in Manhattan and began trying to take back his rackets in the city. Hardly anyone was happy to have him back. On the morning of October 10, 1930, Diamond was wounded by three men who forced their way into his hotel suite and shot him five times. Still in his pajamas, he staggered out into the hall, where he collapsed. He was rushed to Polyclinic Hospital, where he slowly recovered enough to be discharged on December 30. When asked how he had managed to make it to the hallway with five bullets in him, Diamond said that he had already had two shots of whiskey for breakfast.   

On April 21, 1931, Diamond was arrested again, this time on assault charges that dated back to the Parks beating in 1930. Two days later, he posted bond and was released.

A week later, however, he was shot and wounded again. He was at a roadhouse called the Aratoga Inn, near Cairo, New York, which was owned by Jimmy Wynne. Wynne had numerous underworld connection and the nightclub was a popular hangout for gangsters. Diamond had just finished eating with three companions and was waiting on a telephone call from his attorney. As he walked to the front door to get some fresh air, three gunmen who were dressed as duck hunters, opened fire on him. Diamond was hit several times. A local man drove him to a hospital in Albany, where he was treated for his injuries.

His troubles continued. On May 1, while he was still in the hospital, New York State Troopers seized beer and liquor worth more than $5,000 from one of Diamond’s hideouts in Cairo. He was charged with bootlegging and sentenced to four years in state prison. He appealed the conviction and remained free on bail while he awaited the outcome of the appeal.

Meanwhile, Diamond still had to face the music in the Parks case and later that year, he went to trial. He was again acquitted on the assault and kidnapping charges. He left court a free man on December 17, 1931.

In the mood for a celebration, he and his family, along with a few friends, celebrated at the Rainbow Room of the Kenmore Hotel, the best hotel in Albany. At about 1:00 a.m. on December 18, he left the party and went to his see his mistress, “Kiki” Roberts, who was staying at another hotel. Roberts had attended the celebration party, but had left before midnight. Diamond stayed in her room until about 4:30 a.m. and then was driven to 67 Dove Street, a private rooming house where he had been staying during his trial. He entered the locked front door with his key, went upstairs to his room, and fell asleep on the bed.

Witness reports say that a large black car, which had been parked down the street for some time, pulled up to the rooming house soon after Diamond arrived. Two men got out and entered the front door, using a key, and quickly went upstairs. When they got to Diamond’s room they either used a key or, as some believe, Diamond drunkenly left his own key in the lock, and entered the room. Diamond was asleep on the bed. While one man held him down, the other shot Diamond three times in the head.

They ran out of the room, but when they were halfway down the stairs, one of the gunman rack back up, went back into Diamond’s room, and shot him a few more times – apparently, just for good measure. The landlady, Laura Woods, awakened by the shots, overheard the second gunman call out, “Oh hell, that’s enough, come on!” The men left the house and drove away in the black car.

A few minutes later, at 5:00 a.m., Mrs. Woods telephoned Alice Diamond, the contact that Jack had given her in case there was any trouble. Within minutes, Alice, one of Diamond’s men, and Diamond’s eight-year-old nephew, Eddie, arrived at the house. Alice entered the room and began to scream. She frantically wiped blood from his face with a towel while the police and an ambulance were called.  

Like most gangland slayings, the murder was never solved. In this case, there were just too many suspects since almost everyone seemed to want Diamond dead, from Dutch Schultz to the New York Syndicate, relatives of the Cassidy brothers who had been shot at the Hotsy Totsy Club, and even local politicians who wanted Diamond out of the Albany area. It didn’t seem to matter to most who had killed him – there weren’t many who were going to miss him.

Diamond was buried at Mt. Olivet Cemetery in Queens on December 23. There was no church service of graveside ceremony. The burial was attended by Alice, her sister and brother-in-law, three nieces, a cousin, about a dozen reporters, and more than 200 curiosity-seekers. There were no known gangsters in attendance and, against the custom of the day, none of them sent flowers either.  

Diamond may have gotten what he deserved, but there was one sad footnote to the story. On July 1, 1933, Alice Diamond was found shot to death in her Brooklyn apartment. It was speculated that she was killed by her husband’s enemies to keep her quiet, but no one knows for sure. Her murder, like the murder of Jack “Legs” Diamond, was never solved.