The First Mobster to Die in the Electric Chair

The First Mobster to Die in the Electric Chair

Louis "Lepke" Buchalter after the racketeer, the object of a nationwide search, surrendered to J. Edgar Hoover, head of the FBI, in New York.

Why you should care

Because the rackets ruin a lot of lives.

In the Prohibition-era New York gangster scene, Jacob “Little Augie” Orgen reigned supreme as don of the bustling Lower East Side, largely thanks to his lieutenant, Louis “Lepke” Buchalter, a stone-cold killer who was eyeing the top spot all the time he was playing second fiddle. On Oct. 15, 1927, he made his move. Little Augie was meeting a business associate, Jack “Legs” Diamond, on the corner of Norfolk and Delancey in the heart of the Lower East Side, quietly talking business as pedestrians passed by under bright streetlights on a Saturday night.

Suddenly, a black touring car pulled up to the corner. Buchalter and two gun thugs jumped out and ran up behind Little Augie and Legs with revolvers drawn. One gunman shot Little Augie in the back of the head, splattering the gang leader’s brains all over the sidewalk. Pedestrians panicked and scattered screaming as another hit man gut-shot Diamond, who scurried away. But the killers didn’t care about pursuing him; the deed was done.

In the 1930s, Lepke and his vast syndicate of hoodlums spread their greedy tentacles into nearly every form of illegal revenue in New York City.

Avi Bash, crime author

Buchalter was born in 1897 in the same neighborhood where the hit took place 20 years later. His father, who owned a hardware store, died when Buchalter was young, and widow Rose moved her family to Williamsburg, Brooklyn, where Buchalter graduated from P.S. 94 in 1912. His mother called him “Lepkeleh” — Yiddish for “little Louis.” Shortened to Lepke, the nickname stuck, in part because of Buchalter’s stature, 5 feet 6 inches.

Following his brief school career, Buchalter gravitated back to Manhattan and the Lower East Side, where he hooked up with Jacob “Gurrah” Shapiro to rob and extort pushcart owners before going into burglary. Arrested numerous times for assault and theft, the young hoods were making a name for themselves until a second-degree larceny charge in 1918 sent Buchalter up the Hudson River to Sing Sing prison for two and a half years. When he got out in 1922, prison officials claimed he was fully rehabilitated.

They may have been misled by the criminal’s appearance, as others often were. “Lepke’s soft, puppy-dog eyes distinguished him from other gangland contemporaries,” says Christian Cipollini, author of Murder Inc., “but they masked a ruthless business acumen that led to the frequent use of homicide to settle disputes.”

By 1925, Buchalter had begun his rise to the top of the New York crime scene. In addition to working for Orgen, he was also muscle for Arnold “the Brain” Rothstein, a gambling kingpin who is best known for fixing the 1919 World Series. As Rothstein diversified into the garment trade and narcotics, especially smuggling heroin from Europe, he cultivated young thugs such as Buchalter and Charlie “Lucky” Luciano, showing them how to dress and act like gentlemen. “Lepke’s criminal career blossomed under the tutelage of Rothstein,” says Avi Bash, author of Organized Crime in Miami.

Equal parts brutal and cunning, Buchalter combined his mentor’s business tactics with his own penchant for violence to become the czar of the New York labor rackets. He also made a fortune via trucking, heroin, shylocking and extorting the New York film industry. Al Capone even asked him for advice on taking over California’s film industry.

By the late ’20s, Buchalter had a lucrative side hustle as the head of Murder Inc., the feared and seasoned death squad that assassinated anyone for a price. Structurally, organized crime is often compared to a corporation. If true, when it came to Murder Inc., “Lepke’s role would most certainly have to be that of president,” says Bash. A governing board of directors, the National Crime Syndicate, approved and ordered hits, and it was Buchalter and his “vice president” Shapiro who carried out the board’s orders with great proficiency. Crime experts estimate that Murder Inc. executed about 1,000 people in the 1930s and early ’40s.

“In the 1930s,” Bash says, “Lepke and his vast syndicate of hoodlums spread their greedy tentacles into nearly every form of illegal revenue in New York City.” And yet his success drew the attention of both the feds and New York state authorities. In 1937, “feeling the heat of Lady Justice bearing down,” as Cipollini puts it, Buchalter went into hiding for a few years. The feds in particular made sure the gangster’s partners in crime knew that they could make things hot for them as well if Buchalter remained at large.

“Gangland lore has it that Lepke agreed to surrender, but only to the feds for a drug rap,” says Patrick Downey, author of Gangster City: The History of the New York Underworld 1900–1935. But J. Edgar Hoover had no power to make such a deal. When Abraham “Kid Twist” Reles sang to the feds, implicating Buchalter in a murder, the gang leader was soon headed back up the river. On March 4, 1944, he became the first and only mob boss to be executed via the electric chair in Sing Sing known as Old Sparky.

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