Legs Diamond


Legs’s mugshot taken in Philadelphia after getting kicked out of Europe.

by Patrick Downey

Jack “Legs” Diamond is little remembered today, but for the last eighteen months of his life he rivaled Al Capone as the most famous gangster in Prohibition Era America. Whereas Capone was famous for being the CEO of the largest criminal enterprise in the U.S., Jack was famous for getting shot, beating the rap and carrying on a highly publicized extra-marital affair with his Ziegfeld showgirl mistress.

In 1931 alone, Jack appeared in The New York Times on 103 occasions. Nineteen of those appearances were on the front page. A modest number considering that the Times only discussed Jack when there was news fit to print. The tabloids weren’t so choosy: if Jack didn’t do anything worth mentioning, they invented stories for him. If there was a high profile murder in New York City, Jack’s name was somehow dragged into it. If a reader wanted to know how Jack celebrated New Year’s, his birthday or a first night out of jail, for a mere three cents, the dailies were happy to oblige. At the height of his fame, Jack received upwards of a hundred fan letters a day. The movie studio MGM had even considered making a film based on him.

Though Jack was semi-famous on a national level since 1928, it wasn’t until the fall of 1930 that he became an international celebrity. In late August, Legs set sail for Europe to purchase large quantities of narcotics. Sources indicate that he was traveling with at least US $200,000. He managed to slip out of New York harbor aboard the Belgenland without any fanfare, but during the crossing the New York City Police learned about the trip. As a courtesy, they contacted Scotland Yard in London to inform them Jack was on the way.

For years Europeans had read with fascination about America’s Prohibition gang wars and once the English press learned that a bonifide American gangster was on his way over, the press jumped all over the story. For a number of days, the British public was treated to the life and career of Legs Diamond or “Cunning Jackie” as the press called him. Like the New York press, the British papers didn’t let the truth come between them and a good story. One tabloid stated that they had interviewed Jack and that he was already in the country.  This proved false however when the Belgenland docked in Plymouth and Jack was still aboard. The gangster was greeted in his room by members of Scotland Yard and informed that he was considered an undesirable character and would not be allowed off the boat. Jack assured them that he had no intentions of leaving as his destination was the ship’s next stop, Antwerp.

Once Scotland Yard concluded their business with Jack, journalists were allowed in to interview him. Jack assured all that he was simply a businessman taking a trip abroad for health reasons. He blamed all his notoriety on the press. “It’s these newspapers,” he complained, “All the time they are driving the police to do something and they do it. They hold me for a couple of days and all the headlines scream about it. But when they let me go two days later they never say a word about it.”

A wanted poster for Legs

Now that everyone knew that Jack was heading for Antwerp, the U.S. diplomat there was urged by the New York Police to inform Belgian authorities about Jack. He did so, and upon arrival, Jack was told that he was not welcome and had to leave. Told to pick a neighboring country to travel to, Jack chose Germany and, with a police escort, was placed aboard a train. At the border, German police were waiting and Jack was taken into custody. German authorities informed Jack that he was not welcome there either and that he would be deported back to the States. Unable to find a passenger ship with a spare room, Jack, who arrived in a first class cabin, was sent back to America aboard a freighter along with five thousand canaries.

Reporters from numerous cities and newsreel cameras were on hand for Jack’s arrival in Philadelphia sixteen days later. He had no way of knowing it, but the notoriety he encountered during his failed trip to Europe was only the beginning of the whirlwind and he would become even more famous in two weeks’ time.

In the end, it wasn’t for his involvement in narcotics that Jack became famous. His ascent began back in 1927 when he was shot for the second time. (His first dose of underworld lead came in 1925 courtesy of Italian bootleggers whom he had been stealing from.) His recovery was followed in 1928 by a gang war between him and his one-time protégé Dutch Schultz. 1929 brought more headlines when two gangsters were gunned down in Jack’s nightclub the Hotsy-Totsy. Jack spent nearly seven months in hiding until all witnesses were silenced one way or another.

Now, back in New York City, Jack assumed he could continue as always. He began to make arrangements for a return trip to Europe but his underworld investors wanted their money back. Jack stalled them, saying that the fix was in and he would be able to return to make the deals. His investors felt different.

On the morning of October 11, 1930, Jack was sleeping in a room at the hotel Monticello. At his side slept his mistress Marion “Kiki” Roberts, whom he had been seeing since the previous winter. The phone rang. It was the front desk, two guys were there to see Jack. Jack said to send them up. He got up, put on his robe and fished a hundred dollar bill out of his wallet. He left it for Marion telling her that he was going to take the guys to his room across the hall for a meeting. There was a knock at the door, Jack answered it. “Let’s go over to my room where we can talk.” Jack said. The men left and Marion went to the bathroom to run a bath.

Just as she began to soak, Marion heard a number of loud popping noises. A few moments later Jack appeared, his face dripping with blood from a bullet wound in his forehead. His pajama tops were also stained with the crimson fluid, the result of three bullets in the upper torso. Jack told Marion to clear out, which she did, and then he staggered down the hall to the hotel manager’s room.

Marion Kiki Roberts

This shooting, on the heels of the European trip, made Legs Diamond a household name. The papers followed his convalescence for weeks and his and Marion’s picture were splashed all over the dailies. Jack was released from the hospital on New Year’s Eve and, once again, the newsreels were waiting for him. In addition to the cameras dozens of reporters and hundreds of gawkers waited at the train station to see the East Coast’s most famous gangster board the train that would take him to his upstate home.

Through the winter of 1931 Jack regained his strength. In March, he traveled to Chicago where he rekindled his relationship with Marion who was performing there in a show. That spring, Alice, Jack’s wife, caught wind of the affair and left him. Marion moved in with Jack, who was at that time, attempting to monopolize the bootlegging industry in New York’s Catskill region. On April 15, Jack, Marion and two of Jack’s men were returning from a night of drinking when they came upon a pickup truck hauling some booze. Knowing that the stuff wasn’t his, Jack pulled the truck over at gunpoint. The two men inside  were brought back to Jack’s house where one of them, a man named Parks, was tortured for information. The victim said nothing and Jack let him go. The next day Parks went to the police and Jack was arrested. Bail was paid and Jack was released on April 24. Two days later, as he was exiting a roadhouse, Jack was cut down by a number of blasts from an automatic shotgun. For the second time in six months, the fourth time in his career, Legs Diamond was put on the spot by gangland foes and survived. The press had a field day.

The torture story, followed by the shooting, sealed Jack’s fate as a gangster. New York Governor Franklin Roosevelt ordered the States Attorney to crush Jack and his gang. As Legs lay recuperating in an Albany hospital the State went to work building a kidnapping case against him. If that wasn’t bad enough, the federal authorities also began building a bootlegging case against him.

As the world waited to see if Jack would live to set foot in a courtroom the New York dailies filled their pages with stories about their favorite gangster, three of them ran serial biographies on him. Realizing that he needed some positive press Jack sat for an interview with the New York Daily News giving his side of the story, the piece ran as a four part series.

Jack went on trial that July for the kidnapping of Parks and was found not guilty. The people who packed the courtroom and the hundreds who loitered around the courthouse cheered wildly at the verdict. The public loved a gangster who could survive both the bullets of his enemies and the law.

Legs’s release from the hospital, New Years’ Eve 1930

In August, Jack was put on federal trial for bootlegging and found guilty. He managed to get out on bail and have his sentence deferred a number of times in the hopes of getting a retrial.

Unfortunately for Jack, he received millions of dollars’ worth of free publicity in the one industry where publicity is bad: crime. Though the public loved him, Jack couldn’t operate while under the microscope of the press. That fall and winter found Jack living in and around Albany, New York. Low on cash, he moved from rooming house to rooming house trying to survive in the underworld. That December the state put him on trial again, this time for kidnapping Park’s assistant. Once again Jack was found innocent. That night he, his wife and a number of companions went to celebrate at an Albany speakeasy. At about twelve-forty-five in the morning of the eighteenth, Jack lied to everyone in his party and said he had to go meet somebody but would be back shortly. It was the last time they ever saw him alive.

The real reason Jack left the party was to keep a rendezvous with Marion, whom he had living at an apartment nearby. After spending a number of hours with her he had his driver returned him to the boarding house he and Alice were staying at. Jack was extremely drunk and his driver helped him up to his room and then returned to the speakeasy where Alice and the rest of the group were still partying.

Shortly after the driver left, two underworld assassins approached the boarding house and let themselves in. One of the men held a flashlight, the other a .38. They crept up the stairs and entered Jack’s room. The man with the .38 approached the bed and placed his gun a hair’s width from the face that graced thousands of newspapers around the globe. He pulled the trigger three times succeeding where many others failed before. Legs Diamond was finally dead.

Images courtesy of the author.

About the Author:

Patrick Downey has been researching New York’s machine-gun toting, fedora wearing gangsters for over twenty years. His books include: Legs Diamond: Gangster, Bad Seeds in the Big Apple: Bandits, Killers & Chaos in New York City 1920-1940 and Gangster City: The History of the New York Underworld 1900-1935.