He’d been married to his second wife, Alice Kenny, since 1926, but was seen most often on the nightclub circuit with a striking Ziegfield Follies showgirl from Boston who called herself Kiki Roberts (her real name was Marion Strasmick). Kiki was a “bombshell,” according to the tabloids—a red-haired, tough-talking career girl who saw Jack Diamond as her ticket to fame and fortune. While Alice was home tending the domestic front, Legs squired Kiki to the Cotton Club, El Fay, the Stork Club, and, of course, his own Hotsy Totsy Club, where he first met the kid, Vincent Coll.
It was at the Hotsy Totsy that Diamond got himself into a heap of trouble, sending him on a course that would eventually lead to his assassination.
On the night of July 13, 1929, Diamond and a member of his gang, Charles Entratta, were in the club when three dock wallopers from the West Side became drunk and rowdy. When one of the rowdies physically accosted the club’s manager, Diamond intervened.
“I’m Jack Diamond, and I run this place,” he told the three men. “If you don’t calm down, I’ll blow your fuckin’ head off.”
One of the men responded, “You no good for nothin’, you can’t push me around.”
In a matter of seconds, bullets began to fly. The three dock wallopers, all of whom had criminal records, were heavily armed, as were Diamond and Entratta. As shots were exchanged across the dance floor, club patrons rushed for the exits. The band abruptly ceased playing. By the time the dust settled, two of the intruders were dead, shot multiple times in the body and head; the third was rushed to the hospital in critical condition.
More than fifty people, including employees and patrons, saw the shooting, but none would be available to testify against Legs and Entratta. Within six weeks of the double homicide, the club’s manager and three waiters mysteriously disappeared. Their bullet-riddled bodies started turning up in various locations around New Jersey. Other potential witnesses, those who were not eliminated by the dirt nap, were so terrified that they developed a collective loss of memory. The police case against Diamond and Entratta never got off the ground.
The shootout at the Hotsy Totsy Club and murderous elimination of any and all witnesses was one of those Prohibition-era horror shows that was bad for business. The authorities felt compelled to crack down on everyone, much to the annoyance of the Syndicate leaders.
“I told you that playboy Legs was trouble,” the Dutchman chastised Owney Madden.
“I know, I know,” was all Owney could say.
Over the next year there would be three separate attempts on Diamond’s life, all of them close calls. In one of the shootings he was drinking with Kiki at the bar of the Aratoga Inn, six miles outside Acra. Three gunmen dressed as duck hunters burst in the door and filled Diamond with lead. He was rushed to nearby Albany Hospital, where he lingered at death’s door for three days. A doctor who treated him said, “I had to tie off the vessels inside the lung which later collapsed, and then, as the wound started to heal, the lung was expanded by inserting into it a tube of air. The man is a medical wonder.” After three hours of surgery and four weeks of convalescence, Legs was discharged.
“Well,” said Legs to a gaggle of reporters waiting outside the hospital, “I made it again. Nobody can kill Legs Diamond. I am going to settle a few scores just as soon as I get my strength back, you just wait and see.”
Despite the constant threat of assassination, Legs boldly attempted to expand his business operations. He made a second trip to Europe in August 1930, but “big, bad Jackie,” as he was described in the Fleet Street tabloids, received so much negative press that he was constantly under surveillance by Scotland Yard and harassed by German police. Unable to make the major narcotics deal he had hoped for, he left Europe; upon his return via ocean liner, he was again surrounded by reporters. His arrival was even captured by Movietone News, who had only recently developed the technology to accompany their newsreel footage with direct sound.
“Was your trip a success, Legs?” asked an intrepid reporter. “Did you get what you were after?”
For the first time, the general public heard the voice of Legs Diamond: “You fellows know I went to Europe for my health. You aren’t trying to pin something on me, are you? You can tell the public that most of what they have been reading about me is all bunk. I’ve got a lot of legitimate interests.”
Jack returned to his compound in Acra and resumed bootlegging. Upstate, the new thing was applejack, cheap brandy made from apples. In a warehouse distillery Diamond had constructed on his own property, he made Applejack. At a large brewery in the nearby town of Kingston, he produced beer. Most of Diamond’s product, according to local imbibers, was terrible, but Jack took over the booze business upstate the same way bootleggers did in the city—by eliminating the competition through intimidation and murder. Diamond counterbalanced his reputation as a thug by cultivating a reputation for generosity; he gave huge tips everywhere he went and made donations to local youth and church organizations. One local newspaper even described him as “the Robin Hood of Greene County.”
Local authorities frequently raided his compound, at one time estimating his bootlegging operation to be worth $10 million. Despite the profitability of his operation and somewhat glamorous reputation, the harassment from federal agents and violent attempts on his life took their toll. In newsreel footage from the era, Legs often appears as a haunted, spectral figure, gaunt and pale. Granted, much of this footage was compiled as Diamond shuffled to and from hospitals and courtrooms, when he was presumably not in the best of moods. Even so, Diamond’s temperament was becoming a concern.
Those who knew him commented that he seemed to be increasingly irritable and sadistic. The fact that he still carried buckshot embedded in one lung from the most recent attempt on his life couldn’t have helped. Of course, Diamond had always been a cruel and vicious killer, but he now seemed to derive sustenance from his violent acts; it was as if the power he wielded over the lives of his victims was a substitute for the lack of power he had within the granddaddy of all bootlegging empires, the New York City underworld.
Diamond’s nasty side was revealed on the night of April 18, 1931, when he, two members of his gang, and girlfriend Kiki Roberts were driving on a country road near the town of Catskill. Diamond and his gang spotted a truck carrying a load of Applejack belonging to a rival bootlegger. They stopped the truck, and, at gunpoint, forced the truck’s two occupants to come with them. Kiki Roberts was told to go powder her nose. The two rival bootleggers were taken to a garage in back of Diamond’s house. The truck’s passenger, a terrified seventeen-year-old kid who knew nothing, was let go. The driver, a bald-headed unassuming laborer named Grover Parks, was tied and bound.
“Give us the name of your boss,” demanded Legs, “or we’ll beat you to a pulp.”
“I dunno nothing,” said Parks. “Please, let me go.”
Diamond’s gang beat the man with fists and a shovel, then suspended him from the limb of a nearby tree. Parks screamed for mercy to no avail. Legs and his cohorts slugged him in the face and applied lit cigarettes to his bare feet. Every time Parks screamed for help, they beat him some more. Eventually, exasperated by the bastard’s unwillingness to talk, Legs and his crew decided to take a beer break. Diamond told Parks, “When we come back, if you’re not ready to tell us what we want, we’re going to kill you.”
While Legs and his gang were off drinking, the man managed to break free and escape. Bloodied and beaten, he made his way on foot to the Catskill Police station and begged for protection from local authorities.
The county prosecutor’s office was sure they had an airtight case: Diamond and two of his gang were arrested and charged with kidnapping. Legs was released after posting twenty-five thousand dollars bail. Over the following months, publicity surrounding the case was so intensive that a judge moved the proceedings to Troy, in nearby Rensselaer County.
At the trial, prosecutors produced multiple witnesses who claimed to have seen Legs Diamond in or around
the area of the kidnapping on the night in question. A terrified Grover Parks took the stand and told his story. Upon cross-examination, Diamond’s attorney sought to portray Parks as a pathetic publicity hound who was hoping to enhance his social standing in the refracted glow of the defendant’s legend. The trial lasted four days. The jury deliberated for three hours. Legs was found not guilty.
“Gang Law Beats State Law in Diamond Case” blared a headline in the late edition of the Albany Evening News. The verdict seemed to confirm everyone’s worst fears: Justice was a whore.
That night, amid the inevitable cries of jury tampering, Diamond and his entourage retired to the bar of the Kenmore Hotel in nearby Albany. Jack’s wife Alice was there, as was his mistress Kiki, who’d been hidden away in a separate apartment during the trial. That night Legs danced to his favorite tune, “Happy Days and Lonely Nights.” Later, without wife or mistress, he went to a celebration at a popular speakeasy across from Union Station. He got drunk, then went to Kiki’s apartment and got drunker. At some point, Legs stumbled back to the boarding room where he was staying under the name Kelly. He stripped to his underwear and fell into bed.
Around five-thirty in the morning, two visitors entered the boarding house and went to Diamond’s room, which was apparently unlocked. The landlady would later state that she heard Jack Diamond pleading for his life. She also heard one of the visitors reject mercy and tell Legs, “Others pleaded with you.” Shortly thereafter, the sharp retort of gunfire pierced the dawn: three shots, up close and personal. After a lifetime of close calls and near misses, Legs was finally, absolutely, positively dead.
The killers were never identified, though they were seen speeding away in a red Packard. The way the hit went down, it had to have been at least partly set up by local players. In the months that followed, there was much speculation. Could Jack Diamond have been set up by Alice, his long-suffering wife? Was he possibly betrayed by members of his own gang? Did local cops, a fair number of whom were on the payroll of one mobster or another, play a role or even provide shooters to take out the area’s most notorious criminal?
Whoever pulled the trigger, it made little difference. The result was the same: Luciano, Schultz, Lansky, and the others were now one step closer to their grand scheme of establishing an underworld free of uppity Irish gangsters.4
With Friends Like These…
Vincent Coll’s trial for the killing of five-year-old Michael Vengalli got under way in Manhattan on December 16, 1931. If the lad from Gweedore was concerned about his fate, it was with good reason. All he had to do was look at the papers. Jack Diamond had been dramatically acquitted, then summarily executed. Under these circumstances, Coll might have viewed his own trial with considerable trepidation. Would he be better off being found guilty and sent to the electric chair a la Two Gun Crowley? Might his chances be worse if he were acquitted and sent back out into the streets, where he could be hunted down and murdered by the Syndicate?
These were tough times for an enterprising Irish racketeer. The press and the public had already convicted Coll of the horrendous act. Vincent the Mad Dog was a renegade Irish gangster, enemy of the establishment, which made him GUA (Guilty Upon Arrival). Compared to Jack Diamond, Coll was like a platypus wallowing in the mire. Legs had been acclaimed, while Vincent was despised—though they did represent flip sides of the same coin that had been designated for extinction.
At trial, the prosecution’s star witness turned out to be a man who claimed to have been walking along 116th Street in East Harlem on the day in question. While minding his own business, lo and behold, he saw four men in a car driving by. One of those men stuck a machine gun out the back window of the car and opened fire, aiming at a man identified as Joey Rao, but striking instead a gaggle of young children. The triggerman’s face was partially obscured by a fedora pulled low on his head, but the intrepid witness was able to identify the shooter as Vincent Coll because of the prominent dimple in the middle of his chin.
Coll’s criminal defense attorney, Samuel Liebowitz, was on the case. During pre-trial investigations, Liebowitz had learned that the witness, along with being a convicted felon who did time as a jewel thief, was little more than a professional witness, a breed endemic to the criminal justice system. The man had only recently been paid for his testimony at a murder trial in St. Louis, where he was found to have committed perjury.
“Have you ever testified in a criminal proceeding before?” Liebowitz asked the witness on the stand.
The man denied that he had.
“Have you ever been paid, sir, to testify in a criminal proceeding?”
“Uh…no. I have not.”
Liebowitz produced the records from the trial in St. Louis, and the government’s case against Mad Dog Coll was finished. Their star witness was exposed as a cheap fraud. Before it was over, the judge would be compelled to instruct the jury that, given the mendacity of the government’s case, they had no choice but to find the defendant not guilty.
Coll, dressed in his best suit, stepped into the afternoon chill outside the Criminal Courts Building with Lottie, his twenty-three-year-old fiancée, beaming at his side. To the assembled reporters, he read a rare public statement: “I have been charged with all kinds of crimes, but baby-killing was the limit. I’d like nothing better than to lay my hands on the man who did this. I’d tear his throat out. There is nothing more despicable than a man who would harm an innocent child.”
Vincent Coll was released from custody that day, but he was hardly a free man.
In the euphoria of acquittal, he and Lottie were married on January 4, 1932, in a civil ceremony. There was no honeymoon. In the weeks that followed, the two lovebirds were stopped a half dozen times and harassed by cops. They were held on minor matters, such as not having their registration for their automobile. Police authorities made it clear that they would not stop pestering Vincent Coll until he left town and never returned.
The reasons Coll and his bride stayed in the area remain something of a mystery. Vincent may have been delusional enough to believe that he could reemerge as a player in the city’s underworld, though the murder of Legs Diamond should have disabused him of those notions. Nonetheless, he and a small handful of young loyalists sought to reestablish themselves. They set up an informal headquarters at a four-family frame dwelling on Commonwealth Avenue in the northern reaches of Vincent’s home borough, the Bronx.
On February 1, less than one month after Vincent and Lottie’s marriage, three members of Coll’s crew, along with two women and two babies, were in the Bronx apartment. The men were playing cards, and the women were tending to the infants, when a team of four gunmen burst in and began shooting. There was no time for the occupants to return fire. Methodically, the gunmen shot everyone in the room, except for the two babies, who cried hysterically in their cribs. After they were finished, the killers made a hasty retreat.
When the cops arrived, there was blood splattered everywhere. Two of the men and one woman were dead. Another man and woman were badly injured. The whole scene was underscored by the sound of screaming babies. Even by Prohibition-era standards, it was a grisly incident. The tabloids, in typical hyperbolic fashion, compared the shooting to the St. Valentine’s Day Massacre. Police sources speculated that the executioners were actually on the hunt for Vincent Coll and had gone on information that he was due there that night with his bride, Lottie.
Yet again, Vincent and Lottie holed up at the Cornish Arms Hotel on West Twenty-third Street. The entire city knew the underworld was out to get the man; many probably wished that the gangsters would get it over with so that the carnage might end. Star columnist Walter Winchell turned up the heat by narrating the whole thing through his radio broadcasts and his column in the Daily Mirror. Wrote Winchell, “Five plains brought dozens of machine guns from Chicago Friday. Local banditti have made one hotel a virtual arsenal and several hot spots are ditto because Master Coll is giving them the headache.”
Vincent s
ought to buy some time by establishing contact with the only man in the upper echelon of the Syndicate whom he could even remotely call a friend: Owney Madden. He did so in his usual hotheaded, counterproductive style—by threatening to kidnap Madden and hold him for ransom, just as he had done with Madden’s sidekick, Big Frenchy DeMange.
“Just imagine how the dagos and kikes is gonna feel if they gotta shell out a hundred grand to save your sorry ass,” Vincent told Owney. “Pay me now, up front, and I’ll save you the trouble.”
Madden told Coll he’d get back to him. Meanwhile, Madden conferred with Dutch Schultz and decided that the best way to get to the Mick was through one of his bodyguards.
Just after midnight on February 8, Vincent received a call from Madden, who was in his office at the Cotton Club. Concerned that the phone at the hotel might be tapped, the two men agreed that Coll would step out to a pay phone inside a candy store on Twenty-third Street and call Madden back from there. Vincent and his bodyguard, part of a rotating crew he kept on the premises at all times, left the hotel together.
Arriving at the New London Pharmacy and Candy Shop around twelve-thirty A.M., Coll stepped into a phone booth in the rear of the store. The bodyguard took a seat at a counter near the soda fountain. Vincent called Madden at the Cotton Club and was jabbering away when a car pulled up in front of the store. Four men, one of them wearing an ankle-length coat and gray fedora, got out of the car. Three of the men positioned themselves around the drugstore entrance. The man with the long coat and fedora entered the store and nodded to Coll’s bodyguard. Coll’s betrayer swiftly climbed off his stool and skedaddled out the front door.
From beneath his coat, the man in the gray fedora produced a tommy gun. While Vincent chattered on the phone heatedly and obliviously, the gunman approached, raised his machine gun, and fired a short burst into the booth, shattering glass and creating a loud racket. He paused, corrected his aim, and fired again, making sure to riddle Coll’s body from head to toe. The whole thing was over in a matter of seconds.
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