Irving Wexler was a poor kid from the slums of the Lower East Side, so skilled at filching wallets from pockets it was as if they were covered with wax; hence the nickname "Waxey." He picked "Gordon" as a surname.
Waxey met Arnold Rothstein in the days before Prohibition, working in the garment district as a labor enforcer. As anyone familiar with Roaring Twenties history (or the HBO series Boardwalk Empire) knows, Rothstein was a premiere bootlegger, mastermind behind the rigged 1919 World Series, inspiration for The Great Gatsby's Meyer Wolfsheim, and capable of intimating a murder threat through the slightest quiver of an eyebrow.
Waxey became part of his circle, eventually working alongside fellow gangsters Lucky Luciano and Meyer Lansky, and Rothstein became the master of New York City's illegal liquor trade — the largest operation in the country, with an estimated 32,000 speakeasies. At the height of Rothstein's operation, eighty percent of the liquor distilled in Canada found its way to the United States, and the Bahamas' exportation of whiskey increased 425 fold. Determined to take over a number of breweries in New Jersey, Waxey began warring with the Irish gang that controlled them, murdering them one by one. The breweries were technically legal since they manufactured "near beer"; their authentic stuff was produced and transported to bottling and barreling facilities via an intricate, elaborate system of underground pipes. During one raid, federal authorities discovered a 6,000-foot beer pipeline running through the Yonkers sewer system. In New York, Waxey's web of contacts set up neighborhood cordial shops with "importer" or "broker" plates nailed to the door, a clear signal that they were "in the know." To pick up business, these clever proprietors also slipped flyers under windshields and under apartment doors, offered free samples and home delivery, took telephone orders, and urged customers to "ask for anything you may not find" on the menu. For the weekend warriors, steamship lines operating out of New York introduced cruises with no destination at all but the "freedom of the seas."
In 1931, when Waxey met Gypsy Rose Lee in a Manhattan speakeasy, he was 43 years old and married, with three children. He kept his family in a 10-room, four-bath apartment at 590 West End Avenue (paying $6,000 per year in rent at a time the average annual salary was $1,850) and decorated with the help of professionals, including a woodsmith who custom-built a $2,200 bookcase. Five servants catered to their every whim. His children attended private schools, took daily horseback riding lessons in Central Park, and spent summers at their house in Bradley Beach, NJ. He owned three cars, bought $10 pairs of underwear by the dozen, and stocked his closets with $225 suits tailor-made for him by the same haberdasher who outfitted Al Capone. In 1930, Waxey made nearly $1.5 million and paid the United States government just $10.76 in taxes.
Gypsy was just 20 years old at the time and worried obsessively about money — "Everything's going out," her mother, Rose, warned her daily, "and nothing's coming in." She had just scored her first big break in burlesque, working as a headliner for Minsky's Republic on Broadway, but the days of starving on the old vaudeville circuit, eating dog food just to stay alive, were still fresh in her mind. This basement club, along a dingy stretch of Eighth Avenue, was the first speakeasy she'd ever seen. Waxey Gordon took a seat at a nearby table, joined by four bodyguards wearing green fedoras slouched down, shadowing their faces. She knew Waxey was rich and powerful and, most of all, an opportunity, and for once she bided her time, waiting for opportunity to approach her instead of rushing to seize it first.
Gypsy watched Waxey Gordon watching her, his eyes fixed with purpose as he summoned a waiter and whispered in his ear. He watched as the waiter approached her table, hoisting four bottles of champagne high in the air, and as he set them down, saying, crisply, "Compliments of Mr. W." Waxey watched Gypsy sip the champagne and noted the realization pass across her face; accepting his gift was as much an invitation as a courtesy, an implicit agreement that he would open doors she'd be obliged to step through, locking them tight behind her, no matter what she might find on the other side.
"Thank you for the champagne," she told Waxey when he strode over to her table, the bodyguards lined up like ducklings behind him.
He nodded and said, "You can't tell when you'll run into me again," although she did, indirectly, on the phone the following morning. "No names," a strange voice barked at Gypsy. "I'm calling for the friend you met last night." Mr. Gordon, the voice continued, wanted her to visit a certain dentist at 49th and Broadway. She had an appointment the following morning to get her teeth straightened.
The new caps were beautiful, Gypsy thought, and looked like real teeth — no matter that she could no longer eat corn on the cob, or that they felt like pins lodged deep into her gums. Waxey Gordon was another member of her new world, and she was still learning its language, cracking its code. When Waxey told her to keep her new teeth "brushed good," she did, meticulously and obsessively. When he invited her to perform at a benefit for the inmates of Comstock Prison, at which Broadway impresario Florenz Ziegfeld was expected to be a guest, she signed on right away (although her appearance was cancelled when wardens worried she might corrupt prisoners' morals). When Waxey told her he wanted to give her a dining room set for her new home, she could not have been more thankful for the gesture. When Waxey wanted her to appear on his arm or in his bed she obliged, learning to take more than she gave without anyone sensing the difference.
"She was very involved in the underworld," Gypsy's sister, June Havoc, told me. "She was one of their pets, just like Sinatra… it guaranteed things, the kind of things she wanted."
June happened to be in New York the night Waxey Gordon's stolen furniture was scheduled for delivery. She arrived at Gypsy's house in Queens and found her mother wrapped in a bathrobe, popcorn in hand, watching a "blue" movie, a quaint old term for soft-core porn. Gypsy was upstairs primping, brushing her new teeth. At 4 a.m., the doorbell rang, and a team of burly men lugged in a long, carved-oak table and 30 ornate matching chairs, the grandest dining set any of them had ever seen. Waxey Gordon followed and turned toward the stairs, waiting. Gypsy descended, pointing her toes and accentuating each step, an entrance meant for Waxey Gordon alone.
"I'm sorry I took so long," she told Waxey, and then directed his men to the dining room.
Rose turned to Waxey, looking at him through lowered eyes. She smiled and spoke softly: "Well, son," she said, "I am the mother of Gypsy Rose Lee."
"Pleased to meet you," Waxey said.
She pointed a finger at June. "And this is my baby. She used to be somebody, too."
When Waxey left, Gypsy said goodbye, calling him "Mr. Gordon" and shaking his hand. He called her "kid." Rose sighed and said, "Class. Class. No pretense, just honesty himself. In this world of stinkers, just give me a straightforward, true-blue gangster every time."
Two years after they met, Waxey Gordon was arrested on charges of tax evasion. He sent Gypsy a letter, asking if she'd do her old friend a favor, and come visit him at Northeastern penitentiary — it would so impress his fellow inmates. She agreed, but how she dreaded the slow walk to his table in the visiting room, the amplified whistles inside those thin tight walls, the leers that clawed at her back. It was a runway leading to a place out of her control, with no reward at the end. After two visits, she decided she would never go back. "It made me uncomfortable," the stripteaser said, "being on display that way."