Paddy Whacked: The Untold Story of the Irish American Gangster (31 page)

That was the first time they met. The last was when Vincent and Lottie were on the run in Upstate New York. The two gangsters convened secretly near Diamond’s home base in Acra, a small town in Greene County. There they commiserated about their mutual predicaments as gangsters in exile, shut out by the Combine, which had morphed into the Syndicate, an Italian-Jewish consortium that seemed determined to wipe all Irish mobsters off the face of the earth

“It’s that bastard Owney Madden,” Coll told Diamond. “He’s the one I blame for this.”

Legs couldn’t have agreed more. Although it was Dutch Schultz who’d initiated gangland wars with both Diamond and Coll, and Lucky Luciano who’d devised the plan to shut out the Irishers, they both felt Madden should have been on their side. “If the bastard ain’t gonna stand up for his own fucking people, what good is he?” asked Diamond.

The two talked about starting their own bootlegging/crime consortium based in Upstate New York. It sounded like a great idea. They could be the Beer Barons of the Catskills, hiding out in the mountains and firing shots at whoever tried to come after them. Problem was, neither of them had the finances to pull it off. Vincent had lately been cut off from his bootlegging revenues, and Diamond had costly legal problems in the form of a murder trial that was scheduled to take place within weeks. As they said their good-byes that day, they had no way of knowing it would be the last time they saw each other alive.

For Jack Diamond, in particular, the long descent from Combine insider to hunted animal had been a saga of near biblical proportions. Back when Coll was first making his bones as a young upstart with the Dutchman, Legs had already established himself as an independent racketeer in a city crawling with overly ambitious gangsters. Ever since the first known attempt on his life—when his car and body were riddled with buckshot back in October 1924—he’d led a precarious existence. For a time, he tried to steer clear of bootlegging by getting involved in the heroin trade. Luciano had already made millions off dope and so had Rothstein. The potential profits were enormous: In the mid 1920s, one kilo (2.2 pounds) of heroin could be purchased for $2,000. By the time it was cut, diluted, and sold, that same kilo brought in $300,000.

There were plenty of users. Heroin had not yet been classified as a serious narcotic, so the penalties for use were not overly severe. Some World War I veterans had developed a narcotics habit. Among African American jazz musicians and their predominantly white followers (most blacks were banned from or unable to afford entry to the era’s swankiest nightclubs), heroin had become a trendy high, as had cocaine. The most nettlesome commercial problem with both of these drugs was importation.

It was Arnold Rothstein who reestablished ties with Legs in an attempt to strike a major narcotics deal, perhaps the largest ever undertaken at the time. In late 1926, Rothstein sent Legs to Europe to make the necessary purchase and arrange for smuggling the product into the United States. Diamond’s efforts paid off months later when a huge shipment of heroin, morphine, and cocaine—hidden inside bowling pins—was delivered to the Valentine’s Importing Company on Walker Street in lower Manhattan. Over a period of months, drug-peddling middlemen from all over the New York area arrived at Valentine’s to purchase narcotics, conducting their business in the presence of the police—who were in many instances involved in the trade. In July 1928, a special intelligence unit conducted a raid on police department lockers at the 1st Police Precinct and caught seven cops with drugs and cash. Eventually, nearly fifty detectives would be implicated in one of the largest narcotics scandals in the history of the NYPD.

Diamond himself was arrested, but then released on $15,000 bail. The bail bond was posted by the Detroit Fidelity and Surety Company and guaranteed by Rothstein. The charges against him were later dismissed.

Diamond and Rothstein had a falling out over the drug business—one of numerous disagreements in their relationship, which ran hot and cold; they were like two lovers who knew they shouldn’t be together but couldn’t stay apart. This time, as always, the rift was over money. Legs wanted a bigger piece of the pie, and Rothstein resisted. The stakes were enormous. They had been negotiating a massive narcotics transaction with a millionaire Belgian financier named Captain Alfred Lowenstein. It was the sort of deal that, had it gone through, would have made it possible for both men to retire in splendor. The deal disintegrated when Lowenstein, the third richest man in the world, died under mysterious circumstances: He fell—or was tossed—from his private plane while crossing the North Sea from England to Belgium. Four months later, Rothstein’s time on earth also came to a sudden end, when he took a bullet in the belly at the Park Central Hotel.

Lucky for Legs, he was out of town at the time with an airtight alibi—though that didn’t stop Rothstein partisans from exacting revenge. In the months following Rothstein’s death, numerous gangsters associated with Diamond’s crew began to disappear from the face of the earth. They even went after Legs’s brother, Eddie, who was in Denver, Colorado convalescing from a serious bout of tuberculosis (TB). He managed to survive an ambush in which more than a hundred .45-caliber machine gun bullets were unloaded into a car he was driving. Eddie fled Colorado and returned to New York, where his TB worsened. In May 1929, while Capone, Luciano, Lansky, and the others were convening in Atlantic City, Eddie Diamond died in a hospital bed in Upstate New York.

Legs had now entered what would prove to be a permanent state of affairs as an underworld outsider. Other mobsters didn’t seem to like Legs much. Jealousy might have had something to do with it. He was the snappiest-dressed mobster of the era, easily spotted in his custom-fit dark suits, flashy ties, and sporty black-and-white checkered cap. He had a handsome, black-Irish look that fit the public’s idea of a glamorous gangster. He traveled around town by limousine, with an entourage of bodyguards that made him seem like a dignitary. And he almost always had a pretty dame on his arm.

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.