He began life in 1888 as Irving Wexler, but became infamous as Waxey Gordon, a thriving 1920s bootlegger.

"Gordon" was one of several aliases he used. Why this one stuck isn't clear. As for his nickname, many say it came from his skill as a youthful pickpocket, so smooth it was as though his victim's wallets were lined with wax. Or that his hands were a smooth as wax. I've read it both ways.

Sounds good, but I lean toward the version that says "Waxey" was a play on his given name of Wexler, and the nickname was pinned on him while he was a teenage inmate at a New York State reformatory. That he was arrested as a pickpocket at 17 tells me he wasn't all that skillful with his hands.

He tried several jobs, including operating a pool hall and owning small hotels, but it was as a bootlegger in the 1920s, with the blessing of Arnold Rothstein, that he made his fortune. He squeezed out several rivals until he and Dutch Schultz controlled the New York City market, which they agreed was big enough for the two of them. By this time, Rothstein was gone, assassinated in 1928, perhaps on orders from Schultz.

However, Gordon and Schultz continued their peace, until it was shattered in the 1930s when both men became targets of federal investigations, which caused uprisings in both organizations. Two of Gordon's lieutenants were killed when a gang attempted to assassinate their boss, who escaped through a window. A few days later, another Gordon soldier was killed.

Gordon survived physical threats. What brought him down was the information being fed to the government, which was closing in on him for income tax evasion.

Syracuse Journal, May 22, 1933
New York (INS) — Waxey Gordon, New York’s “public enemy number one,” admitted to authorities today that he was in the Elizabeth-Carteret Hotel in Elizabeth, New Jersey, on the afternoon of April 12 when gunmen murdered Max Hassel and Max Greenberg, alleged beer racketeers.

Gordon made this admission to New Jersey authorities who questioned him at the federal building here where he was arraigned and held in $100,000 bail for early trial on charges of evading $382,976 taxes on his income of $1,616,900 in 1930 and 1931.

The kingpin racketeer had been captured yesterday at a hunting lodge near Monticello, New York. The federal authorities are trying to send him to the Atlanta penitentiary in the same manner in which they put Al Capone behind bars.

Gordon denied all knowledge of the actual killings. He said he was in another room on the eighth floor when he heard the shots.

He said that when he heard the shots, he “beat it.”

The double murders of Hassel and Greenberg, the latter said to have been a partner of Gordon, was one of the underworld sensations of the new “legalized beer era.”

Hassel and Greenberg were found in Room 824 of the hotel, riddled with bullets. Three bullets had been pumped into Hassel. Two of them entered his head, one pierced his chest.

Greenberg was found slumped in a big swivel chair before a desk, three bullets in his head. In his pockets were $1,737 in currency and a loaded .32-caliber revolver.

Gordon’s two bodyguards, Harry Klein, alias Herman Pincus, and Joseph Aront, were arrested with him. Waxey was indicted April 27 for income tax evasion and had been missing since the indictment was returned.

On December 2, 1933, a federal jury found Gordon guilty of income tax evasion. He was fined $100,000 and sentenced to 10 years in prison, but he was released in 1940. He declared himself broke, perhaps to wiggle out of the $2 million tax lien the government had against him.

He was arrested again in 1942 and was sentenced to a year in prison for selling sugar on the black market. Later he turned to the drug trade, and on March 7, 1952 was indicted as boss of a network of dope distributors.

Because of his criminal past, Gordon was held in prison, first in Sing Sing, then Attica. Stays at both prisons were brief. He was a troublesome inmate, so he was shipped across the country to Alcatraz in San Francisco Bay, to await his trial in the city by the bay. He didn't live long enough for another day in court. On June 24, 1952, he suffered a heart attack in the Alcatraz hospital, and died. He was 64 years old.

In his heyday, Waxey Gordon lived the high life, and today is remembered as the man who had Gypsy Rose Lee's teeth straightened. He spotted the stripper one night in 1931 at a New York speakeasy. She was just 20 years old, coming out of nowhere to become the top attraction at Minsky's Burlesque.

From across the room, Miss Lee looked stunning, so Gordon sent four bottles of champagne to her table, where she was sitting with her mother, the now infamous Rose Hovick.

Minutes later, Gordon approached the table, and he and Miss Lee made small talk. While not attracted to the overweight, 43-year-old bootlegger — she thought he looked like a lawyer — she knew she might be highly rewarded if she made nice with him. Having gone through a very tough patch after her sister, "Dainty June," left the vaudeville act early in 1929, the former Louise Hovick wasn't sure her surprising success on the burlesque circuit would continue. So there were plenty of things she'd do for money, including prostituting herself for a married man who had three children.

However, as Gordon said his goodbye that night at the table, with four of his underlings standing behind him, he fought back a grimace when Miss Lee flashed a smile.

As he left, he supposedly told one of his pals, "She's a great-looking broad, but those chompers have gotta go."

He made a dentist's appointment for her the next day, and for two years Waxey Gordon was Gypsy Rose Lee's sugar daddy.

Among his gifts was a dining set that was delayed after his promise, probably because it took awhile for his gang to steal one that was fancy enough for her. It was a housewarming present; she had invested her earnings in a home in Queens.

The delivery was made in the wee small hours of a morning, and Gordon accompanied the men who brought the table and chairs into the home. Gypsy Rose Lee was upstairs; her mother let the men in. A curious visitor was 19-year-old June Hovick, apparently already estranged from her husband. She was competing in marathon dances and just happened to be in New York City for a few days.

Rose introduced herself to Gordon, then pointed toward June, and explained that she was her baby. "She used to be somebody, too," she snapped.

Gypsy Rose Lee paid for the gifts in the expected way, as Gordon liked to show her off to his friends and associates. And after he landed in prison, he asked her to visit him for the same reason. Word is, she made only two visits before she'd had enough of their relationship.