Born Louis Bookhouse in the Brownsville neighbourhood of Brooklyn, New York, Buchalter was a member of the Amboy Dukes, a street gang in Brownsville named after Amboy Street (a local road), as a young man. He became involved in push cart shoplifting and by 1919 had served two prison terms. Together with friend Jacob "Gurrah" Shapiro, he then gained control of the garment industry unions in Manhattan's Lower East Side; he used the unions to threaten strikes and demanded weekly payments from factory owners while simultaneously dipping into union bank accounts. His control of the unions later evolved into a general protection racket, extending into such areas as bakery trucking. The unions were an extremely profitable venture for him, and he kept an iron grip on them even after becoming a big-time player in the mob.
Buchalter's general protection racket was an idea used by gangsters all over New York City; what made Buchalter stand out from the rest of the pack, however, was his intolerance of those who didn't pay him. With other hoods, a person who defaulted on payments would get their legs broken. In Buchalter's case, if someone didn't cough up the cash, they were simply killed: no second chances whatsoever. Not only would his henchmen kill shopkeepers, they would loot the place before the killing and then burn it afterwards. Buchalter learned the general order of things early on: loot, rape, pillage, then burn. His eventual Achilles heel proved to be an informant who said he was behind two out of every three arsons in Manhattan.
Buchalter's success with the protection rackets shot him to the top of the crime world; the piles of money he raked in were being coveted by old-school Mafia chieftain Salvatore Maranzano by 1929. So, for help, Buchalter went to an old and good friend: Lucky Luciano. Luciano first arranged the rubout of Maranzano's hated rival, Joe Masseria, using Bugsy Siegel, Joe Adonis, Vito Genovese, and Albert Anastasia as the executioners; he then engineered the elimination of Maranzano, establishing himself as the top mob boss in New York City.
In the early 1930s, Luciano, Buchalter (who had taken on the nickname Lepke, meaning "Little Louis" in Yiddish), and Johnny Torrio (the former Chicago boss and mentor of Al Capone) formed the National Crime Syndicate, an umbrella organization of all major organized crime groups coast-to-coast. As a founding member, and also as a reward for his support of the murders of Masseria and Maranzano, Buchalter obtained a seat on the Syndicate's "board of directors". In order to take care of "problems", Luciano's associates Bugsy Siegel and Meyer Lansky formed Murder, Inc Originally a band of Brooklyn killers of mostly Jewish origin, they were highly effective and eventually used to fulfill most Syndicate contracts. Control of the group soon passed to Buchalter and Albert Anastasia, as Siegel and Lansky had bigger fish to fry.
Buchalter was a nasty, vicious man, probably the bloodiest Jewish gangster of all time. He constantly wore wool suits, but they couldn't warm up his eyes, which were said to be like blocks of ice. He never really killed anybody himself, but was adept at commanding others to do the dirty work for him. He would order assassinations on the phone from his grandmother's house without so much as batting an eye. As many as a hundred corpses have been attributed to Buchalter himself; those under his control may have slain a thousand more nationwide. Some of the more famous hitmen at his disposal included the brutal Abe Reles, Seymour Magoon, Frank Abbandando, Harry Maione, Allie Tannenbaum, and the infamous Harry Strauss. Major Murder, Inc. rubouts included Dutch Schultz in 1935 and even Bugsy Siegel in 1947, although Siegel's murder took place three years after Buchalter's death. Buchalter naturally attracted a lot of attention from the FBI during the early 1930s, but thanks to bribed federal judges and having other friends in high places, got off scot-free every time.
Buchalter's downfall began in the mid-1930s, when he went on the run from both the FBI, who wanted to nail him on a narcotics charge, and New York City special prosecutor Thomas E. Dewey, who wanted him put away for his Syndicate activities. He was tricked by a childhood friend into surrendering to the feds in exchange for not getting turned over to Dewey, and ended up getting incarcerated at Leavenworth on a 14-year term for narcotics. The sentence was later extended to 30 years by Dewey on account of the union rackets.
On 13 September, 1936, Buchalter's men murdered Brooklyn candy store owner Joseph Rosen, a former garment industry trucker who was told to shut up and get out of town but didn't. The order for the hit had been overheard by Abe Reles, who turned informant for New York State in 1940 and fingered Buchalter for four murders. Brought from Kansas to New York City to stand trial for the Rosen slaying, Buchalter's position was worsened by the testimony of another turncoat, Allie Tannenbaum. A mere four hours after they were handed the case, the jury arrived at a verdict at 2 a.m. Buchalter was guilty of murder of the first degree, and the penalty at the time for such a crime in the state of New York was death by electrocution.
Buchalter was convicted in December 1941, and the New York State Court of Appeals, upon review of his case, upheld his conviction in October 1942. At the time, Buchalter was serving out his racketeering sentence, and New York demanded that he be turned over to them for execution. The gangster put up a valiant fight, calling in favours from friends in the Department of Justice and the courts, and managed to stay out of New York's hands until January 1944. Once turned over, his execution was originally slated to take place on 2 March, but the state's highest court decided to give the case one last look, forcing Dewey (who was now state governor) to grant Buchalter, Mendy Weiss, and Louis Capone (no relation to Al) a 48-hour reprieve. Buchalter sought to bargain with Dewey: he would give the governor (who was running against Franklin Delano Roosevelt for president in that year's election) information about the criminal wrongdoings of some high-ranking U.S. public officials in exchange for the revocation of his execution, but Dewey, to his credit, was not willing to compromise his integrity even at the expense of the presidency, and would have none of it. Buchalter had run out of luck.
Louis "Lepke" Buchalter, arguably one of the most powerful figures in organized crime history, was executed in Sing Sing's electric chair on 4 March, 1944.