The Untold Story of the Diamond Brothers Gang

This photograph, which was taken in 1926, is quite an unusual police line-up for in 1926 these four were known as the Diamond Brothers gang, headed by the infamous Jack “Legs” Diamond and his younger brother Eddie. Also in the photo is Thomas “Fatty” Walsh, another notorious figure of his time. And at the end, is Salvatore Lucania better known as Charles “Lucky” Luciano.

“Legs” Diamond was seen as a mentor to some of the younger up-and-coming generation of mobsters, such as “Lucky” Luciano and Dutch Schultz. Luciano was badly beaten when he was abducted and questioned in connection in the whereabouts of “Legs” Diamond was in a police investigation.

Schultz was close enough with Diamond to sign his name to identify Diamond’s passport. Diamond was heading to Europe to conduct what was believed to have been a narcotics deal. However, Diamond and Schultz would later fall out and go to war with each other, it wasn’t uncommon for Legs Diamond to fall out with business partners.

All four of the men in the photo had several threads connecting them to each other and other events.  

At the time of this photograph, all four were all reputable mobsters in their own right, and some of them were also bodyguards for Arnold Rothstein or “The Brain” or “The Big Bankroll” as he was also known.

In the 1920s, Arnold Rothstein was one of the biggest racketeers and bootleggers in the United States. Arnold “The Brain” Rothstein had become a powerful crime boss, with powerful political connections to New York’s vastly corrupt Tammany Hall political organization.

Rothstein was alleged to have been involved in one of the biggest sporting scandals of the early twentieth century, the 1919 World Series baseball game between the Cincinnati Reds and the Chicago White Sox. Although there was no concrete evidence to connect Rothstein to the scandal, it certainly did add to his legend.

One author, David Pietrusza, suggests that Rothstein worked both ends of the racket with Joseph “Sport” Sullivan and Abe Attell, the heads of two syndicates that were also involved in the betting. Rothstein was never convicted in the subsequent investigation into the World Series betting scandal, although he did testify to a Chicago grand jury, in order to clear his name.  

Arnold Rothstein was murdered in 1928 two years after this photo was taken, in what was deemed a gambling dispute. Rothstein was shot on the 4th of November but died two days later on November 6th. Luciano, Diamond, and Walsh were all brought in or sought for questioning about the murder of Arnold Rothstein.

“Legs” Diamond had fallen out with Rothstein, while “Fatty” Walsh had left Rothstein’s employment some weeks previous as he was “too cheap” according to Walsh. It was reported that Rothstein was paying Diamond, Walsh, and Eugene Moran $1,000 each.

On his deathbed Rothstein refused to co-operate or name the shooter, answering the police’s questions saying “You stick to your trade. I will stick to mine.”

George “Hump” McManus, another gambler who its believed Rothstein owed money, was arrested, tried, and acquitted with a lack of evidence. However, there was some controversy involved in the trial as McManus had political connections to Tammany Hall too.

Now back to this photo, all four were brought in for questioning in connection with a Felonious Assault. They were supposed to have taken part in an attempted robbery of Charles Haffman & Albert Levi.

On 1st December 1926 a car carrying Charles Haffman & Albert Levi was driving around Central Park, Albert Levi was reported to have $8,000 in his pocket. As they were driving toward 105th Street, a car with four men pulled up next to them, one of the passengers shouted “Pull over there. We know what you got”

With that Haffman and Levi drove faster, one of the passengers in the chasing car fired a couple of shots, smashing the glass and hitting Levi in the wrist and right arm. Then the car pulled over, and the four occupants of the other car jumped out and ran to the parked car and began to tussle with Levi, he put up a fight and a crowd began to gather, so the four jumped back into their car and drove off.

In the hospital Levi identified the four men, Charles Haffman confirmed their identities, and 20 detectives were sent out to hunt the attackers and soon arrested Eddie and Jack Diamond, “Fatty” Walsh, and “Lucky” Luciano.  

Two of the four were taken to the hospital, so they could be further identified by Albert Levi, however, Levi suddenly forgot who his attackers were, he said “There’s some mistake, these aren’t the men”

Back at the police station, all four were questioned about another unrelated shooting, and then released. “Lucky” Luciano was issued with a summons to appear in traffic court, while Eddie Diamond was re-arrested in connection with a hold-up from the previous week.

The brothers raided everywhere that stored anything of value. It would have been around this time that the Diamond brothers met up with a very young Charles “Lucky” Luciano or Salvatore Lucania as he was officially known. Just as the prohibition era was kicking off, the Diamond brothers became involved with Arnold Rothstein.

It’s not clear as to how Arnold Rothstein came into contact with the Diamond brothers, but it’s likely that Rothstein was the fence for their stolen loot, and liked what he saw in the Diamond gang. Rothstein had a keen eye for talent and later took “Lucky” Luciano and Meyer Lansky under his influence.

Tuberculosis had ravaged Eddie as well as other members of his family. Eddie had been sent to various sanatoriums to try to get cured but there was little success or improvement recorded. “Legs” sent Eddie to Colorado on one occasion as he thought the mountain air would help him and also because New York had become dangerous.

“Legs” had fallen out with Arnold Rothstein, who Diamond believed had set him up in a European narcotics deal. With “Legs” Diamond in hiding, to get to “Legs” they decided to whack Eddie

The hitmen hired apartments in the city and over the next few weeks, they were able to track Eddie and get to know his movements better. Having been tracking Eddie for a couple of weeks, the hit team parked their car, they planned to wait until Eddie turned onto the street in his car and then start shooting.

Eddie was driving home with his bodyguard, Louis Bifano, when they turned onto the street, the gunmen opened fire and a few of the bullets went into the windshield but somehow the bullets missed both Eddie and Bifano. Eddie crashed the car though, and both Eddie and Bifano made a run for it, the gunmen chased them.

Bifano got away by escaping down the side passage of two houses. Eddie ran into a house and escaped through the back, the gunman that had been chasing him saw that Eddie had escaped, gave up, and went back to his car. Later Eddie and Bifano were arrested brought in for questioning and released.

“Legs” Diamond fresh from the heat of the Hotsy Totsy Club shootings, put his own plan into action, calling in some favors. When the dust had settled gangland victims were laid out in the morgue. None of them were Eddie Diamond.

Eddie Diamond did die however, Tuberculosis finally caught up with Eddie and he died on the 14th of January 1930.

“Legs” Diamond, was one of the most notorious mobsters during the Prohibition era. John or Jack Diamond was born in Philadelphia, Pennsylvania but moved to New York along with his father and brother, Eddie, when his mother died of Tuberculosis.

He became a prominent figure in American organized crime during the 1920s and early 1930s. They said that “Legs” Diamond was as popular in New York as Al Capone was in Chicago.

“Legs” Diamond became a mentor for some of the younger generation of mobsters, such as Salvatore Lucania better known as “Lucky” Luciano. And Arthur Flegenheimer better known as Dutch Schultz.

Diamond had a reputation for double-crossing partners or hi-jacking their booze shipments, eventually he ran out of partners.

“Legs” Diamond and Dutch Schultz became bitter enemies as a result of Diamond’s treachery and they went to war with each other. Diamond survived several attempts on his life throughout his criminal career, earning him the nickname “The Clay Pigeon of the Underworld”, having 81 shotgun pellets lodged in him and numerous other bullets. People would joke that when he walked he jingled.

The Hotsy Totsy Club was owned by “Legs” Diamond and his partner Charles Entratta or Charles Green as he was also known. Charles Entratta was said by some to be Diamond’s bodyguard but it appears that he was Diamond’s partner in the club.

An argument broke out in the club one night, one man, Simon Walker died after being shot in the head and another, William “Red” Cassidy died later in hospital after being shot three times in the back. Peter Cassidy, Reds brother, was injured when he was shot twice, in the melee in which 15 shots were fired.

One of the staff cooperated with the police and became a witness, which meant some of the other staff had to be whacked so they couldn’t confirm what the witness had seen. One by one witnesses went missing, Tommy Ribler and Hymie Cohen were never seen or heard of again. While William Wolgast’s body turned up riddled with bullets.

Diamond had sent his brother Eddie to Colorado because New York was too hot and could relieve Eddie’s Tuberculosis. Rothstein had a hit team dispatched to Colorado who had been following Eddie for a few weeks before the hit.

However, a series of events happened that would change gangland. On the Fourth of November 1928, Arnold Rothstein was fatally shot. The following day, the Fifth of November, there was an attempted hit on Eddie Diamond in Colorado, Eddie survived and the gunmen, Gene Moran a former Rothstein employee, and Joseph Piteo, a Dutch Schultz gunman, got away and skipped $5,000 bail.

Arnold Rothstein died the following day, the Sixth of November. Although the media linked “Legs” Diamond to the murder of Rothstein, an unconnected man named George “Hump” McManus would eventually stand trial and be acquitted of his murder.

That series of events sparked reprisals. In March 1929 Frank “Blubber” Devlin who was the driver of the hit team in Colorado, was found shot dead.

In August Gene Moran’s charred remains were found in his burned car, he had been shot to death.

In September James Batto’s body was found in a car, he had been shot 3 times. Batto was believed to be Gene Moran’s killer. Two days later Tommy Ahearn’s body was found, and he was named as another of Gene Moran’s killers.

November saw Mortimer Schubert’s body being found, Schubert had been burned with cigars and torches, his ear cut off and six bullets in him. Schubert was also named as one of Gene Moran’s killers.

And finally on the 10th of January 1930 Harry Veasey, a Rothstein associate, was found shot to death in his car in New Jersey. Veasey was the suspect in the murder of Frank “Blubber” Devlin

Another murder that happened in March 1929, the murder of Thomas “Fatty” Walsh, initially appeared to be connected to the other murders. But it turned out that there was a different motive in Walsh’s murder. Walsh, however, was connected to Rothstein, the Diamond Brothers, and Moran

For much of this series of events, both Entratta and “Legs” Diamond were in hiding, Entratta however was caught in Chicago, taken back to New York, brought to trial, and acquitted with a lack of evidence. However, there was still no sign of “Legs” Diamond anywhere.

He eventually deemed it safe enough to come out of hiding, after the witnesses had been taken care of and surrendered to the police for questioning. He posed outside the police station to prove he had no marks on him before he went in.

Jack Diamond’s criminal career came to an end when he was shot and killed in Albany, New York, on December 18, 1931. The same day he had been found not guilty in court.

Because of his treacherous ways, gangland widely snubbed Diamond’s funeral thus depriving him of the gangster’s lavish funerals that were popular during the 1920’s often attracting thousands of mourners and curious onlookers and large floral bouquets worth thousands of dollars.

“Legs” Diamond’s wife Alice Kenny Diamond was also murdered sometime after his death, her murder was also never solved.

Charles Entratta or Charles Green was murdered in July 1931, a gunman burst into his office and began firing at him, suddenly two more gunmen ran in and all three emptied their guns into Entratta. It is believed that it was revenge for the murder of William “Red” Cassidy at the Hotsy Totsy Club.

“Fatty” Walsh was a former bodyguard of Arnold Rothstein. When Arnold Rothstein was murdered, Walsh along with other infamous mobsters, Jack “Legs” Diamond, “Lucky” Luciano, and George Uffner were sought or taken in for questioning regarding the murder, they were all released though.

Thomas “Fatty” Walsh had quit working for Rothstein two weeks previous to the murder as he said Rothstein was “too cheap”. “Fatty” Walsh and Gene Moran parted ways with Diamond after the death of Rothstein. It was a partnership that didn’t last long however, Gene Moran would be “Taken for a ride” by gangsters and his bullet-ridden charred remains were found in his burning car

In March 1929 “Fatty” Walsh was murdered in a hotel room in the Biltmore Hotel in Florida, and another man, a former Diamond gangster, Arthur L. Clark, was wounded but he refused to talk to the police, nor would he even speak of Walsh, “I don’t care to talk” would be his answers to questions  

The investigation suggests that the entire floor of the Biltmore Hotel was rented to a man named “Carl Gaylord”. Whether Carl Gaylord was a real person remains unknown, it was likely a cover name for someone else. Both Walsh & Clark were employees of Gaylord and not registered as guests at the hotel.

It’s said that an illegal speakeasy and Casino was being operated in all six rooms on the 14th floor of the Biltmore Hotel in Florida. Hotel workers would report that fashionably dressed people would make their way to and from that hotel floor.

On the night of the murder of “Fatty” Walsh, gunfire broke out in one of the rooms at 12.45 am killing Walsh and wounding Clark in the side and arm. When police arrived they found the hotel floor deserted and an open door, police found the body of Walsh and an injured Clark lying on the floor groaning. Police would not arrest anyone in connection with the incident.

A man named Eddie Wilson was believed to have been the shooter, an arrest warrant was issued for him, but none were ever charged for the murder. Some witnesses say that “Fatty” Walsh owed money to Eddie Wilson, Wilson confronted Walsh about the money and “Fatty” Walsh began to mock the way Wilson spoke, with a lisp. This enraged Wilson who opened fire and then ran away.

A few other theories emerged — one connected the murder to Rothstein’s murder in New York a few months earlier. Another claimed Walsh got whacked over a bootleg liquor deal gone south, a recent shipment of rye whiskey was stolen and Walsh was said to be one of three men behind the heist, leaving one investor out of pocket to the tune of $175,000.

“Legs” Diamond, in an exclusive interview with the New York Daily News in 1931, refutes any claims that Walsh’s death had anything to do with him or Eddie. Interestingly, Diamond denies that it was Walsh or Gene Moran who shot at Eddie Diamond in Colorado. He would also say about Gene Moran, “he was neither my friend nor my enemy”

The murder of “Fatty” Walsh yielded a lot of ghost rumors over the years. The suite where Walsh was murdered is said to be one of the most active areas in the hotel. Many witnesses over the years have reported they entered this elevator and hit their floor button. Still, the elevator proceeded to ignore this and instead took them directly to the 13th floor. They all report that the doors opened to this floor’s suite and then just stayed open. And the lights in the elevator flicker on and off, some even reported smelling cigar smoke

In the aftermath of the Hotsy Totsy Club shootings, where an argument broke out in the club, one man died after being shot in the head and another died later in hospital after being shot three times in the back. The Hotsy Totsy Club shootings were the start of a series of murders that shocked New York.

Three months after the shooting police were still looking for Legs Diamond, officials, and the media were putting pressure on police to solve the case, running out of ideas they decided to pay Diamond’s old friend Charles “Lucky” Luciano a visit.

Luciano and Diamond had met each other sometime in the early to mid-1920s, they were friends and both had worked for Arnold Rothstein. Luciano was ahead of his time and didn’t mind working with criminals from other ethnic backgrounds, this kind of thinking would come to be important in Luciano’s later years. Luciano also ran clubs and speakeasies on Broadway.

According to author Patrick Downey in the book Legs Diamond, Gangster On October the 16th 1929 as Luciano left a racetrack and was going to a house he owned in the Bronx, he pulled his car into the garage of the house, as he pulled the door of the garage down he was grabbed by a couple of big detectives, who had tailed him from the racetrack.

The detectives threw Luciano against the wall of the garage and frisked him. “I’m pretty sure they were cops the minute I saw them” Luciano would recount years later. “Then a car with two more guys pulls up to the curb. Each one of ’em takes hold of an arm and hustles me into the car and throws me face down in the back”

While he was in the back of the car Luciano said his hands were tied behind his back and tape placed over his eyes and mouth. Then the detectives proceeded to beat and question him as to where “Legs” Diamond was, Luciano told them he hadn’t seen Diamond for over a year, needless to say, the detectives weren’t happy with his answers so they beat him some more and kept questioning him, after a few hours the detectives came to the conclusion that Luciano wasn’t going to give anything up.

They took a ferry ride to Staten Island where they dumped a semi-conscious Luciano on the beach. When he regained his senses Luciano began to make his way home, however, he met a policeman whom Luciano offered $50 to call him a taxi and leave him be, the officer refused and brought him to the hospital, where he was questioned further about grand larceny of an automobile and pursuit from police, that happened a month prior, supposedly with Eddie Diamond in the car.

Luciano gave a statement that he had been picked up by rival mobsters in a limo and beaten. The newspapers picked up on the story, saying he had survived a one-way ride.

The truth is, Luciano was not taken for a ride by rival gangsters. In his words, “A gang ride ended one way…Dead”.

This is where some of the myths about Luciano began. He did not get his scarred face from being hung up by his thumbs, stabbed, and slashed, as some news reports have claimed and he didn’t get the nickname Lucky from surviving the ride, as others have claimed. He was already known to police as Lucky by the time this incident occurred.

Frank Costello once said, “I never heard anyone call him Lucky. Not even behind his back. We called him Charlie, the older guys called him Salvatore, on the street they called him Charlie Lucky”.

A few short years after this photo was taken, three of the four men would be dead, Eddie & “Legs” Diamond and “Fatty” Walsh. Charles “Lucky” Luciano would go on to become legendary. Luciano is credited with creating the modern-day mafia and founding one of the most iconic mafia families, the Luciano Family, which included Frank Costello and Vito Genovese as his Consigliere and Under Boss.

Vito Genovese would eventually succeed Luciano and Costello, which would change the family name to Genovese Family, the Ivy League of organized crime.

Luciano however, was sent to prison and then deported from the United States, Luciano went into exile in Italy where he died in 1962 at the age of 64. Its believed that Salvatore Lucania or Charlie Lucky or “Lucky” Luciano was one of the few mobsters that “Legs” Diamond never double-crossed.

Sources:

The Commercial Appeal (Memphis, Tennessee) · 6 Nov 1928, Tue · Page 11
Daily News (New York, New York) · 19 Nov 1928, Mon · Page 2
Fort Collins Coloradoan (Fort Collins, Colorado) · 25 Nov 1928, Sun · Page 12
Daily News (New York, New York) · 29 Jul 1929, Mon · Page 203
Times Union (Brooklyn, New York) · 17 Oct 1929, Thu · Page 3
The Brooklyn Daily Eagle (Brooklyn, New York) · 17 Oct 1929, Thu · Page 22
Daily News (New York, New York) · 18 Jan 1930, Sat · Page 103
Daily News (New York, New York) · Sat, Mar 22, 1930 · Page 164
Daily News (New York, New York) · 30 Mar 1930, Sun · Page 4
Daily News (New York, New York) · 13 Oct 1930, Mon · Page 7
Daily News (New York, New York) · 13 May 1931, Wed · Page 318
Daily News (New York, New York) · 24 May 1931, Sun · Page 323
Daily News (New York, New York) · 29 Jun 1931, Mon · Page 60
Daily News (New York, New York) · 28 Jun 1931, Sun · Page 90
Daily News (New York, New York) · 30 Jun 1931, Tue · Page 18
The Standard Union (Brooklyn, New York) · 6 Jul 1931, Mon · Page 1
Daily News (New York, New York) · 7 Jul 1931, Tue · Page 268
Daily News (New York, New York) · 24 May 1931, Sun · Page 322
The Brooklyn Daily Eagle (Brooklyn, New York) · 18 Dec 1931, Fri · Page 26

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