Mobsters in America – Louis "Lepke" Buchalter – The Only Mob Boss To Be Executed by the Government

He was bad to the bone from the time he was born. He swindled, he strong-armed and he killed men with relish. In the end, for his many crimes, Louis “Lepke” Buchalter became toast in Sing Sing’s electric chair.

Louis Buchalter was born in Williamsburg, Brooklyn on February 12, 1897. His parent were Russian Jews and his father owned a hardware store on the Lower East Side of Manhattan. Buchalter led an uneventful life as a child. He often walked across the Williamsburg Bride with his father to accompany him to work. His mother affectionately called him “Lepkeleh,” which is Yiddish for “Little Louis.” His childhood friends shortened that to Lepke, a name which stuck with him for the rest of his life.

Lepke’s life took a turn for the worst when he was 13. His father died unexpectedly, and his mother was so overwrought by her husband’s death, her health began to seriously deteriorate. Doctors told her she needed a change of climate to regain her health, so Lepke’s mother left for Arizona, leaving Lepke in the charge of his older sister. Lepke, deeply resentful for being abandoned, was impossible for his sister to control. Soon he left school and started hanging out on the streets of the Lower East Side, looking for trouble and mostly finding it. He hooked up with older gangsters, who taught him how to rob and steal, and how to jack old ladies for their valuables. In 1915, Lepke was caught robbing a store and sent to live with an uncle in Bridgeport, Connecticut. There he continued his thieving ways and was finally sent to a child reformatory in Cheshire.

A few months later, Lepke, now barely 16, was back roaming the streets of the Lower East Side. He took to stealing pushcarts, and one day, he tried to rob a pushcart that was already being robbed by another street tough named Jacob “Gurrah” Shapiro. The two became fast friends and started a relationship that would last the rest of their natural lives. Lepke and Shapiro teamed up and were the menace of the downtown pushcart owners. They tried to climb the latter to bigger scores, but in 1918, Lepke was caught robbing a downtown loft, and as a result, he was sent to Sing Sing Prison on a five year sentence.

Lepke’s time in prison was the equivalent of a college education for criminals. When he was released in 1923, at the age of 25, he was now a hardened thug, with the knowledge to make it big in a life of crime. He teamed up again with his old pal Shapiro and they decided they could make a mint selling “protection” to bakeries all throughout New York City. Other crooks called them “The Gorilla Boys,” and Lepke and Shapiro convinced such big-time outfits like Gottfried’s, Levy’s, Fink’s and California Pies, that they could prevent “crazy immigrants” from burning down their bakeries. Of course the crazy immigrants were “The Gorilla Boys” themselves, and those who did not pay protection indeed did get their bakeries burned down.

The next step up for “The Gorilla Boys” was as schlammers, or leg breakers for the unions. Under their boss Little Augie Orgen, Lepke and Shapiro made a fine living keeping garment district union members in line. Orgen was annoyed by the competition from Dopey Benny Fein, who was muscling in on Orgen’s union territories. So Orgen sent Lepke and Shapiro to straighten out Fein with bullets. The duo cornered Fein in a Bowery bar, but they were only able to wound him, while Shapiro took a bullet in the back. Orgen himself took care of Fein soon after, consolidating his hold on the unions. But then Lepke and Shapiro got the bright idea of taking care of their boss in the same manner that Orgen did to Fein. And that they did, filling Orgen with lead on a Lower East Side street, while Orgen’s bodyguard Jack “Legs” Diamond stood nearby, not doing much of a job protecting his boss.

Orgen’s murder propelled “The Gorilla Boys” into the big time. They became instant stars in the underworld, palling out with such mob greats as Meyer Lansky, Bugsy Siegel, Frank Costello, Albert Anastasia, Dutch Schultz, Tommy Lucchese and Lucky Luciano. Their specialty was working both ends of the union deals; blackmailing owners into paying protection, and charging union member high fees, while skimming a nice cut for themselves off the top of an ever-growing pot of union cash. Industries such as the poultry business, garment center, restaurants and the cleaning and dieing businesses, paid Lepke and Shapiro, who had upwards of 250 thugs now working for them, an estimated $10 million a year just to stay in business. In order to show the government some legitimate income to justify their luxurious lifestyles, Lepke and Shapiro, no longer called the “Gorilla Boys” but instead the “Gold Dust Twins,” acquired legitimate businesses like Raleigh Manufacturing, the Pioneer Coat Factory and Greenberg and Shapiro.

Lepke, along with Luciano, Schultz, Lansky, Siegel, Costello, Anastasia and Lucchese formed a national crime syndicate, which controlled every illegal activity in the northeast, and as far away as the mid west. Of course, to have such an operation to continue to prosper and grow, some times dissidents, inside and outside the group, need to be “straightened out,” or in other words — killed. The syndicate put Lepke in charge of the murder department, with kill-crazy Anastasia as his underboss. They expertly ran what was called by the press, “Murder Incorporated.” Lepke employed gunsels like Abe “Kid Twist” Reles, Harry “Pittsburgh Phil” Strauss, Happy Maione and Dasher Abbandando, amongst others, to travel wherever they were needed, to straighten out whatever person needed to be straightened out.

Trouble arrived for Lepke in the name of Special Prosecutor Thomas E. Dewey, who had already jailed Luciano on a trumped-up prostitution charge. Dewey went after Lepke for his bakery extortion rackets, but Dewey came down harder with the hammer, when he got the Federal Narcotic Bureau to build a case involving Lepke in a massive drug smuggling operation. Figuring he was facing big time in the slammer, Lepke went on the lam. He was concealed in several Brooklyn hideouts by Anastasia, while his rackets were tended to by other member of the syndicate.

Lepke’s actions had an adverse affect on the rest of his pals. J. Edgar Hoover, obviously ignoring that Hitler and Mussolini were wrecking havoc throughout the world, said Lepke was “the most dangerous man on earth.” As a result, a $50,000 reward was offered for Lepke’s head. New York Mayor Fiorello La Guardia added to the heat, when he ordered his police commissioner Lewis J. Valentine to start a “war on hoodlums.” Things got so bad, a message was sent to Luciano, who was cooling his heels in the can, for some sage advice as how to handle the Lepke matter. Luciano decided that for the common good, Lepke, after nearly four years on the run, had to turn himself in and face the music.

The trick was how to convince a man, who was facing 30-years-to-life in prison, to give himself up and take his medicine like a man. Luciano, ever the wily fox, constructed a plan, whereby Moe “Dimples” Wolensky, a man Lepke trusted, convinced Lepke that a deal had been made with Hoover, that he would be tried only on the narcotics charge and get five years in jail, at most. And if Lepke surrendered directly to Hoover, Dewey would then be out of the picture completely. Lepke had his doubts, and when he asked Anastasia for advice, Anastasia, obviously not in on the deal, told Lepke, “This deal sounds screwy. As long as they can’t get you, they can’t hurt you.”

On August 5, 1940, gossip columnist and radio host Walter Winchell got a phone call at his nightly stomping grounds, the Stork Club, at 3 East Fifty-Third Street. A gruff voice on the other end said, “Don’t ask who I am, but Lepke wants to come in. Contact Hoover and tell him Lepke wants a guarantee he will be not be harmed if he surrenders to Hoover.”

The very next day, Winchell went on the radio. He said, in his usual staccato delivery, like a machine gun firing from his mouth, “Your reporter is reliably informed that Lepke, the fugitive, is on the verge of surrender, possibly this week. If Lepke can find someone he can trust, I am told, he will come in. I am authorized by the G-men that Lepke is assured of safe delivery.”

On August 24, 1940, Winchell received a phone call telling him to go to a drug store on Eighth Avenue and Nineteenth Street, and to sit in a phone booth in the back. At 9 pm a customer casually walked over to Winchell, and told him to phone Hoover and tell Hoover to be at Fifth Avenue and Twenty Ninth Street at 10:20 pm. Winchell himself was told to drive immediately to Madison Avenue and Twenty Third Street. Winchell did as he was told, and at 10:15, Lepke, wearing a mustache as part of his disguise, entered Winchell’s car. Minutes later, the two men exited Winchell’s car and walked to a black limousine. Hoover was sitting alone in the back seat.

Winchell opened the back door of the limo and said, “Mr. Hoover, this is Lepke.”

Hoover said to Lepke, “How do you do?”

Lepke said to Hoover, “Glad to meet you. Let’s Go.”

Almost immediately, Lepke knew he had been hoodwinked. In a few days, Hoover told Lepke there had been no conditional deal for his surrender. Lepke was tried on the narcotics charge and sentenced to 14 years. But then the roof fell on Lepke, when, after his first trial, Hoover handed Lepke over to Dewey, to stand trial for the murder of an innocent schmo named Joe Rosen, whom Lepke ordered killed in 1936. Rosen was murdered because he threatened to go to Dewey and tell him that Lepke had stolen Rosen’s trucking business. As a result, Lepke’s boys put 17 bullets into Rosen. At Lepke’s murder trial, a sting of rats, including Abe “Kid Twist” Reles, testified that Rosen was killed under Lepke’s orders. After a short deliberation by the jury, Lepke was found guilty and sentenced to death.

Lepke lost appeal after appeal for a full four years, and was scheduled to be executed on March, 2, 1944. Then suddenly, on the day he was to be executed Lepke dropped a bombshell, when he requested a meeting with New York City District Attorney Frank Hogan. Lepke told Hogan he had information of political corruption that went all the way up to the President of the United States, Franklin D. Roosevelt. Lepke got a 48-hour reprieve and Hogan went to Dewey, who was now Governor of New York, and the only one who could stop Lepke’s execution. Hoover told Dewey Lepke’s story. Dewey, who would later run unsuccessfully for the Presidency, turned a deaf ear to Lepke, sealing his fate.

On March 4, 1944, Louis “Lepke” Buchalter, knowing he had been stiffed by his best friends, and with no trace of emotion, or remorse, was executed in Sing Sing Prison’s electric chair.


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