Irving Penn was a short, fat man who was in the sheet music publishing business and had the bad luck to resemble a short, fat man named Philip Orlovsky, who was in the rackets. On Tuesday the 25th of July 1939, the gunmen waiting to whack Philip Orlovsky made an honest mistake.
Accidents happened, but this particular wrong-man murder brought down a lot of clamor, and now the underworld as well as the forces of justice deemed it time to do something about fugitive crime boss Louis Buchalter, aka Louis Lepke. Orlovsky was one of District Attorney Thomas Dewey's witnesses, no few of whom had been getting exterminated lately; now an innocent had died. Suddenly a blue-ribbon grand jury was rounding up everyone Lepke ever knew. "Those other mobsters won't be able to stand the pressure," one detective assessed things. "They'll force Lepke to take the rap to save their own hides, or else we'll find his bullet-riddled carcass some morning."
Holed up in Manhattan for two years while authorities searched as far afield as Palestine and Poland, Lepke divined that this was probably true. There was a difference between being a powerful gang boss no one could refuse to harbor and a hunted animal who was raining down grief on everyone's heads. Lepke was bad for business. He was, as they said in gangland, a hot article. Prison was clearly the safest place for him to be.
So it made good sense to surrender, although certainly not to Dewey, who had enough state charges on him to send him over for hundreds of years, maybe even fry him. What did the federals have? Flight to avoid prosecution for violating the Sherman Anti-Trust Act, that's what. That sounded like maybe a couple of years in the joint. What Lepke needed here was somebody who could set this up.
Walter Winchell of the Daily Mirror, well known to be very tight with the Federal Bureau of Investigation, got the call on Saturday the 5th of August. "Lepke wants to come in," a voice informed him.
"But he's heard so many stories about what will happen to him," the voice continued. "He can't trust anybody. The talk around town is that Lepke would be shot while supposedly escaping."
"I'll tell John Edgar Hoover," Winchell said. "I'm sure he will see to it that Lepke receives his constitutional rights and nobody will cross him."
"Put it on the air," the voice said, and on his network radio broadcast the next night, with Hoover sitting beside him, Winchell mysteriously informed a certain unidentified party, "if you're listening," that a deal was arrangeable.
There were a couple more calls over the next couple of days, and then they stopped, and this of course was because Lepke was getting to be a hotter article every minute. Even Gurrah Shapiro, his only friend in the world, would have cheerfully blowtorched him to death at this point.
Lepke and Gurrah had been pals since they were kids knocking over pushcarts. Strange pair that they were, Lepke the crafty businessman and Gurrah the big stupid bone crusher, they had nonetheless always been side by side in the rackets, working together as rag-trade strikebreakers for Little Augie Orgen and then taking over garments for themselves after Little Augie expired in 1927. It was Lepke who figured out that you could move in on both the manufacturers and the unions simultaneously and strategically stick your own people everywhere, and this was a very fine arrangement until Tom Dewey got named special prosecutor in the summer of 1935 and the whole house fell down.
Specifically, there was the matter of Billy Snyder. Billy had been a union president who didn't care to have mobster partners, and one night in September 1934 he had rejected a business plan offered over dinner in an Avenue A restaurant and a dim little thug named Morris Goldis had shot him to death in front of 13 witnesses. Manifestly, this job had been done at the behest of Lepke and Gurrah, and Billy Snyder, brave albeit dead, went on to serve as something of a call to arms for Dewey and his racket smashers as they first put away Charles Luciano and then turned their attentions to Charlie Lucky's two apparent successors.
Law-enforcement turf wars being what they were, the federals got to Lepke and Gurrah first, and in the spring of 1937 they both went down on anti-trust counts relating to the fur business. Whereupon, sensing Dewey's hot breath on their necks, they both jumped bond and vanished. Whereupon Dewey, piously invoking Billy Snyder's name at every turn, was elected district attorney of New York County and started making agreeable witnesses out of Morris Goldis and numerous other hired hands.
Gurrah gave himself up in April 1938. Several potentially talkative parties had already been murdered, and word was out that Lepke was quite prepared to silence Gurrah too. In court, the big ox bawled like a baby and went off to the federal pen.
By August 1939, Lepke was obviously on the spot; Dewey was confident he would come in momentarily, the better to stay alive. This was very good, as Dewey was at this moment unofficially launching a 1940 run for the presidency. Nobody bothered to tell him that Lepke was already reaching out to the FBI, turf wars being what they were.
Walter Winchell at his desk.
(Bettmann)John Edgar Hoover recognized Walter Winchell to be a useful publicist, and he put up with quite a lot from him, but he was plenty dubious about this Lepke surrender business, and after two weeks of silence his patience was wearing thin. "This is a lot of bunk, Walter," the FBI chief informed the columnist. "You are being made a fool of and so are we. If you contact those people again, tell them the time limit is up and I will instruct my agents to shoot Lepke on sight."
When, on Wednesday the 22nd of August, a stranger stopped Winchell on Fifth Ave. and reinitiated discussions, Winchell announced that surrender time would be the next day, period. And at 6 p.m. Thursday, as per arrangement, he was waiting at a phone booth.
A caller instructed him to drive to a Yonkers theater. He did. There he got a message to drive back to a Manhattan drugstore. He did. Nursing a Coke at the fountain, he was then joined by a gent who ordered him to park at Madison and 23rd and wait. He did.
Shortly after 10, America's most wanted man climbed into Winchell's car. "Thanks very much," he said.
Hoover, as per arrangement, was waiting alone in a government sedan at Fifth and 28th.
"Mr. Hoover, this is Lepke," said Winchell.
"How do you do," said J. Edgar Hoover.
"Glad to meet you," Lepke grunted. "Let's go."
Walter Winchell, not one to trivialize his triumphs, reproduced in the Daily Mirror the official letter he had no doubt insisted that Hoover cough up. "Without your unselfish and indefatigable assistance, I know that Buchalter would not have surrendered," the G-man wrote. "In rendering this aid you have performed a most patriotic service, not only to your government but to the American people."
The other papers reported that Lepke had turned himself in through "an intermediary."
Louis Buchalter, safe behind bars, made no attempt to secure counsel and eagerly looked forward to serving out his soft federal stint until such time as Tom Dewey might no longer be DA. He had misapprehended things, however; the feds gave him 30 years and then handed him off to the state, which efficiently convicted him of murder. In March 1944, quite stunned, Lepke became the only major American crime boss ever to go to the electric chair.
First published on May 29, 1998 as part of the "Big Town" series on old New York. Find more stories about the city's epic history here.
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