Jack “Legs” Diamond and the Myth of the Man Who Would Not Die
- Daniel Holland
- 9 hours ago
- 13 min read
On the morning of 18th December 1931, a boarding house on Dove Street in Albany was unusually quiet. Inside one of the upstairs rooms, Jack “Legs” Diamond lay face down on his bed, fully dressed, dead from three bullets fired at close range into the back of his head. For more than a decade, gunmen had tried and failed to kill him. This time, there would be no recovery, no hospital bed, no wry comment to reporters. The man the press had christened the “clay pigeon of the underworld” was finally finished.
Diamond’s reputation for survival had become so entrenched that his death felt almost implausible. Rival gangster Dutch Schultz had once complained to his own men, after yet another failed attempt,
“Ain’t there nobody that can shoot this guy so he don’t bounce back?”
For years, the answer had been no. But in Albany, in the early hours of a winter morning, someone finally managed it.
An Irish American Childhood That Gave No Warning
Jack “Legs” Diamond was born John Moran on 10th July 1897 in Philadelphia, Pennsylvania, to Irish immigrants Sara and John Moran. Some later records give his birth year as 1898, but contemporary documentation supports 1897. His parents had emigrated from Ireland in 1891, part of a working class migration driven by stability rather than sudden opportunity.
Biographer Patrick Downey later noted that Diamond’s early life did not conform to the familiar caricature of the future gangster. “He didn’t live in an overcrowded squalid tenement,” Downey wrote, “nor did he have to face the problems and confines that those new arrivals from Europe had to face.” The family lived modestly, but not in extreme poverty.
That relative stability collapsed with illness. Diamond’s mother suffered from severe arthritis and recurring health problems, dying on 24th December 1913 after a bacterial infection and high fever. Her death fractured the family. John Moran moved his sons to Brooklyn, where they drifted between relatives and boarding houses. Jack struggled in school, briefly passed through a juvenile reformatory, married young, and divorced almost immediately. The pattern of restlessness had begun.
The Hudson Dusters and an Early Criminal Identity
By his mid teens, Diamond had joined the Hudson Dusters, a Manhattan street gang known for its volatility rather than strategic organisation. His first recorded arrest came on 4th February 1914, when he was caught burglarising a jewellery shop. It was a minor crime in a city drowning in petty offences, but it marked his first permanent entry into police records.
In 1917, Diamond enlisted in the United States Army during the First World War. His service was brief and undistinguished. He went absent without leave and was convicted of desertion in either 1918 or 1919. Sentenced to three to five years at Leavenworth Military Prison, he served two before being released in 1921. The experience hardened him rather than redirected him.
Arnold Rothstein and a Criminal Education
After his release, Diamond became a hired enforcer and later a personal bodyguard for Arnold Rothstein, the gambler and fixer whose influence reshaped organised crime in New York during the early 1920s. Rothstein operated with discipline, scale, and political awareness, and Diamond absorbed those lessons quickly.
By the mid 1920s, Diamond’s circle included figures who would later dominate American organised crime. These included Fatty Walsh, Charles Entratta, Salvatore Arcidiaco, international con man Count Victor Lustig, and a then little known Salvatore Lucania, later called Lucky Luciano. It was a volatile network built on opportunity rather than loyalty.
Prohibition and the Rise of “Gentleman Jack”
When Prohibition came into force in 1920, Diamond found his economic footing. Unlike bootleggers who focused on distillation or large scale smuggling, Diamond initially preferred hijacking. Trucks carrying illegal alcohol were easy targets, and their owners could not turn to the police. It was quick, violent, and profitable.
Diamond cultivated a flamboyant persona. He dressed sharply, drank heavily, and danced enthusiastically. His nickname “Legs” was said to derive either from his skill on the dance floor or from his ability to flee danger at speed. His wife, Alice Kenny Diamond, disapproved of his criminal life but did little to intervene. His most visible companion was Marion “Kiki” Roberts, a Ziegfeld Follies dancer who would later be central to his final months.
Diamond ran speakeasies, most notably the Hotsy Totsy Club on Broadway, and developed increasingly elaborate supply schemes. One involved dumping liquor barrels overboard near Long Island and paying local children a nickel for every barrel they retrieved. Another centred on the Barmann Brewery in Kingston, which appeared abandoned while a rubber hose ran through half a mile of sewers to a bottling warehouse.
When federal agents raided the brewery in 1931, they seized 3,000 barrels of beer, 41,000 bottles, and so much cash that newspapers dubbed it the “million dollar seizure”. Diamond was not arrested that day. He was in hospital, recovering from gunshot wounds.
Bloodshed and Reputation
Violence followed Diamond relentlessly. On 24th October 1924, he was wounded by shotgun pellets during a hijacking attempt. On 16th October 1927, while substituting as bodyguard for his brother Eddie, Diamond was shot twice during the murder of Jacob “Little Augie” Orgen on Manhattan’s Lower East Side. Orgen died. Diamond survived.
Police interviewed him in hospital. Diamond refused to identify suspects. He was briefly charged with homicide before the case collapsed.
On 14th July 1929, Diamond and Charles Entratta shot three men during an argument inside the Hotsy Totsy Club. Two died. Witnesses disappeared. One was later found dead in New Jersey. Diamond was not charged, but the club closed. The New York Daily News began referring to him as the “clay pigeon of the underworld”, noting in one column that he appeared “constructed of material not available to ordinary men”.
The Man Who Refused to Die
Between 1924 and 1931, Jack “Legs” Diamond survived at least four serious assassination attempts, though contemporary police files suggest there may have been more minor attacks that never reached the courts or press. Across these incidents, he was struck by more than seventy buckshot pellets and nearly a dozen pistol bullets. Each time, he recovered. In an underworld where men were routinely killed for far less provocation, this pattern was extraordinary.
Diamond’s survival was not merely physical. Each failed attempt seemed to strengthen his standing, feeding the belief among allies and enemies alike that he was unusually resilient, perhaps even reckless to the point of invulnerability. Newspapers increasingly framed him less as a criminal and more as a recurring figure in an ongoing drama, wounded, hospitalised, and then inexplicably back on his feet.
The most notorious of these incidents occurred on 12th October 1930, while Diamond was staying at the Hotel Monticello on Manhattan’s West Side. Two gunmen forced their way into his room and shot him five times at close range. The attack appeared calculated to be fatal. Diamond was hit in the chest and abdomen, wounds that would ordinarily have proved lethal.
Instead, still wearing his pyjamas, Diamond reportedly poured himself two shots of whisky before staggering into the corridor, where he collapsed. Hotel staff summoned assistance, and he was rushed to the Polyclinic Hospital. Surgeons later described his survival as improbable. Despite the severity of his injuries, Diamond recovered once again.
When questioned by police during his convalescence, Diamond expressed neither gratitude nor humility. “Every time I get shot, they arrest me instead of looking for the guy who shot me,” he complained. The remark reflected a recurring grievance. In the eyes of law enforcement, Diamond was not a victim of violence but a constant suspect, regardless of who pulled the trigger.
Barely five days after being released on bond for kidnapping charges in April 1931, Diamond was shot again, this time at the Aratoga Inn, a roadhouse near Cairo, New York. He had been dining with companions when gunfire erupted. Struck three times, Diamond collapsed near the entrance. The attackers fled immediately.
Rather than waiting for authorities, a local resident placed Diamond in a car and drove him directly to hospital in Albany. Once again, he survived wounds that many believed should have killed him. According to hospital staff, Diamond told the attending surgeon, “They have not yet made the bullet that will kill me.” Whether bravado or genuine belief, the statement circulated widely and became part of his growing legend.
These repeated survivals had unintended consequences. Far from deterring further attempts, they increased pressure on Diamond’s enemies to finish the job decisively. Rival gangsters viewed his continued existence as destabilising, while newspapers treated each recovery as a provocation. Even Diamond himself seemed aware that his luck could not hold indefinitely. His behaviour grew more erratic, his drinking heavier, and his willingness to place himself in dangerous situations more pronounced.
By 1931, Diamond’s reputation as a man who could not be killed had hardened into something close to fatalism. Allies admired it. Enemies resented it. Law enforcement dismissed it. When death finally came, it arrived not in a chaotic shootout or public ambush, but quietly, in a rented room, while he slept.
The European Failure
In August 1930, Jack “Legs” Diamond quietly left the United States aboard the transatlantic liner Belgenland, travelling under the alias John Nolan. The trip was not a holiday. Diamond was carrying approximately $200,000, a substantial sum supplied by racketeers Salvatore Spitale and Irving Bitz. Officially, the money was intended to finance a liquor importing operation, exploiting perceived gaps in European supply chains during Prohibition. Unofficially, federal authorities suspected something far more serious.
The United States State Department received advance intelligence that Diamond was heading to Europe, though agents were initially unsure which vessel he had boarded or which name he was using. Customs officials believed Diamond was not travelling alone. Reports suggested that Charles Entratta, Salvatore Lucania, Salvatore Arcidiaco, and an associate known only as Traeger were also involved, possibly dispersing once they reached the continent to avoid detection.
Diamond spent much of the Belgenland crossing in the ship’s smoking room, playing poker. One newspaper claimed he won thousands of dollars during the voyage, though the ship’s officers later disputed this, stating that his winnings were modest. Regardless, his presence did not go unnoticed. American authorities transmitted warnings to police agencies in England, France, and Belgium, describing Diamond as an undesirable criminal figure.
When the Belgenland reached Plymouth on 31st August 1930, British authorities refused to allow Diamond to disembark. Speaking to reporters, Diamond claimed he intended to travel to the French spa town of Vichy “for the cure”, a statement few took seriously. Instead, he was permitted to leave the ship at Antwerp on 1st September 1930, where Belgian police detained him for questioning.
Belgian authorities ultimately declined to prosecute, but they made it clear that Diamond was not welcome. He was placed on a train bound for Germany. When the train reached Aachen, German police arrested him immediately. Classified as an “undesirable alien”, Diamond was held briefly before the German government ordered his deportation.
On 6th September 1930, Diamond was transferred to Hamburg and placed aboard the cargo ship Hannover, bound for Philadelphia. When the vessel arrived on 23rd September 1930, Diamond was taken into custody by Philadelphia police. At a court hearing later that day, a judge offered him a stark choice. He could be released immediately, provided he left the city within an hour. Diamond agreed.
He returned from Europe empty handed. There were no drugs, no liquor deal, and none of the money entrusted to him. In the weeks that followed, rumours spread quickly through the underworld that Spitale and Bitz were demanding answers. Letters recovered later from Diamond’s residence appeared to support suspicions that the mission had involved narcotics rather than alcohol. For many observers, the failed European venture marked the point at which Diamond’s luck began to turn decisively against him.
Trials and Folklore
By the early 1930s, Diamond had accumulated more than twenty arrests across multiple jurisdictions, yet convictions remained rare. Charges ranged from assault and bootlegging to kidnapping and torture. Again and again, cases collapsed due to missing witnesses, uncooperative victims, or juries that appeared remarkably sympathetic to the defendant.
One 1931 trial in upstate New York captured the peculiar position Diamond occupied in the public imagination. As proceedings adjourned for the day, a young boy in the courthouse gallery reportedly shouted, “They’ll never get Legs!” The comment was noted by reporters and repeated widely. It was not an endorsement of Diamond’s crimes so much as an acknowledgement of his apparent immunity to consequence.
Newspapers increasingly treated Diamond as a recurring character rather than a conventional criminal defendant. His hospitalisations, court appearances, and acquittals became episodic updates in an ongoing story. For many readers, the question was no longer whether Diamond would be convicted, but whether he would survive long enough to face another trial.
That spring, journalist John O’Donnell of the New York Daily News entered into an unusual arrangement with Diamond. O’Donnell was one of the few reporters Diamond tolerated, and the two struck a quiet deal. Diamond agreed to provide interviews and background information on his life and career, on the condition that nothing would be published while he was alive.
“When I’m dead,” Diamond told O’Donnell, “you can print this stuff.”
The remark was not theatrical. Those who heard it later recalled it as resigned rather than defiant. By 1931, Diamond appeared to understand that his continued survival had become improbable. His acquittals had not reduced the number of people who wanted him dead. They had increased it.
The Last Night
On 17th December 1931, Diamond was acquitted yet again, this time in Troy, New York, on charges related to kidnapping. The verdict followed a familiar pattern. Despite the seriousness of the accusations and Diamond’s reputation, the prosecution failed to secure a conviction. Court observers noted little surprise in the outcome, and rumours of jury tampering circulated almost immediately, though no evidence was ever produced.
Diamond left the courthouse a free man, once more having slipped through the legal system. That evening, he celebrated with family members and close associates at a local restaurant in Albany. Witnesses later recalled that Diamond drank heavily and appeared unusually relaxed, even by his own standards. Some remarked that he seemed relieved rather than jubilant, as if the strain of repeated trials had finally begun to wear him down.
As the night wore on, Diamond separated from his group and travelled to the Kenmore Hotel on North Pearl Street. There, in the Rain Bo Room, a popular nightclub known for live music and late hours, he was joined by Marion “Kiki” Roberts. The pair remained at the club into the early hours of the morning, drinking and talking as the room gradually emptied. Staff later described nothing out of the ordinary, only that Diamond was visibly intoxicated when he finally left.
At around 4.30 a.m., Diamond took a taxi back to the boarding house at 67 Dove Street, where he had been staying during the trial. He returned alone. According to the proprietor, Diamond said little, climbed the stairs unsteadily, and entered his room. Fully clothed, he collapsed onto the bed and quickly fell asleep.
Approximately an hour later, at around 5.30 a.m., two men entered Diamond’s room. Investigators later determined that there were no signs of forced entry. One man restrained Diamond while the other fired three shots at close range into the back of his head, just below the left ear. The positioning of the wounds indicated that Diamond was either asleep or too intoxicated to resist. There were no defensive injuries and no evidence of a struggle.
The killers fled the scene almost immediately. A boarding house resident later reported seeing two men leave the building and drive away in a dark coloured sedan bearing Brooklyn licence plates. A revolver and a flashlight, wrapped in silk, were later recovered from the lawn of St Paul’s Church less than a mile away, but they were never conclusively linked to the crime.
Police arrived shortly after the discovery of the body. Diamond’s wife, Alice Kenny Diamond, had been alerted and rushed to the scene. Officers found her in a state of visible distress, cradling her husband’s head and repeatedly saying, “I didn’t do it.” The scene was chaotic rather than theatrical, marked by confusion and shock rather than any sense of final reckoning.
Official reaction was notably unsympathetic. New York Police Commissioner Edward P Mulrooney summed up the prevailing law enforcement view when he told reporters, “So they got him at last. It’s no loss to the community not this community anyhow.” The remark reflected both Diamond’s long criminal history and the exhaustion felt by authorities who had watched him evade conviction for years.
Within hours, speculation about the identity of the killers began to circulate, but the investigation quickly stalled. As with many gangland murders of the Prohibition era, the combination of silence, fear, and political entanglement ensured that the case would remain unresolved.
Who Ordered the Killing
Suspects ranged from Dutch Schultz to Spitale and Bitz to the Albany police themselves. Author William Kennedy later recorded claims by political boss Dan O’Connell that Diamond had been executed on his orders to prevent outside gangs muscling in on Albany. “He wanted to go into the insurance business here,” O’Connell said. “I sent word that he wasn’t going to do any business in Albany and we didn’t expect to see him in town the next morning.”
Diamond was buried on 23rd December 1931 at Mount Olivet Cemetery in Queens. There was no church service. Around 200 people attended. No major criminal figures were seen.
On 1st July 1933, less than eighteen months after Jack Diamond’s murder, his widow Alice Kenny Diamond was found shot dead in her Brooklyn apartment. She was thirty three years old. The killing attracted far less public attention than her husband’s death, but it quietly reinforced the sense that the consequences of Diamond’s life did not end with him.
Police were alerted after neighbours reported hearing a gunshot. Alice was discovered inside her apartment with a single gunshot wound to the head. There were no clear signs of forced entry, and no weapon was recovered at the scene. The circumstances suggested that she may have known her killer or had admitted them voluntarily, though investigators were unable to establish this with certainty.
In the months following Jack Diamond’s death, Alice had struggled financially and socially. She attempted to capitalise on her husband’s notoriety by selling her story to newspapers and exploring book and film deals, but none materialised in a meaningful way. According to contemporary reports, she had also fallen in with a new circle of acquaintances connected to the fringes of the underworld, a development that concerned both family members and police.
Rumours circulated almost immediately that Alice had been killed to prevent her from revealing damaging information about her husband’s associates or the circumstances of his murder. Others suggested the killing was connected to disputes over money or to personal relationships formed after Diamond’s death. None of these theories were ever substantiated. As with Jack Diamond’s murder, no one was arrested, and no charges were brought.
The investigation faded quickly. By the summer of 1933, public appetite for Prohibition era gangland stories had begun to wane, and Alice Diamond’s death did not fit the mythic narrative that had surrounded her husband. Her case remains officially unsolved,
The boarding house at 67 Dove Street still stands. It was sold in November 2023 for $375,000.
Jack “Legs” Diamond never became another Al Capone. But for a decade, he survived bullets, courts, and rivals so consistently that his continued existence became a kind of problem. When death finally arrived, it was swift, unceremonious, and entirely fitting for a man who spent his life assuming tomorrow was guaranteed.
