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Big Bankroll.” He would become the biggest bootlegger in New York, but back then he was making his money fixing horse races. Which is how Jay came to know him. So, you see, if Jay wasn’t deep in the underworld, he certainly got his feet wet flitting around its shores. He and Rothstein remained friends and business partners. In 1923 Rothstein was called to testify in the bankruptcy hearing of an associate, E. M. Fuller, during which he was made to reveal that he had recently loaned Jay twenty thousand dollars.
    Jay’s pal Al Davis certainly had a reputation on Broadway as a “sharpshooter,” as one paper put it, a man able to make a living “through his wits in a score of ways.” One of which, it turned out, was convincing a wealthy young woman named Eugenia Kelly, the “first flapper of Broadway,” that he was a man worth marrying. The two of them burned through twenty thousand dollars of her million-dollar fortune in the space of nine months. Her mother called Davis a “tango pirate.” She was so disgusted by their affair that she tried to have her daughter arrested on the grounds that she was an “incorrigible person.” She tookher to court, just so she could expose the mess Davis had made of her inheritance. Eugenia’s sister was Helen Kelly, better known as Princess Vlora, whom we met in the last chapter. She was a lifelong friend of Jay’s from their days running around Broadway. The Eugenia Kelly case caused real outrage and prompted a group of the more upstanding members of New York society to launch a “moral crusade” against the “social gangsters” who frequented the Broadway dancing palaces.
    Again, then, Jay had to find another way to get his kicks. In 1914 he started betting on professional sport. He won $10,000 on the World Series that year by backing the Boston Braves against the Philadelphia Athletics. He was offering bets around town, staking $1,200 on the Braves to $2,000 against the Phillies at first, then more still at odds of 2–1. He won a large chunk off Rothstein, through the bookmaker Sport Sullivan. Rothstein and Sullivan would go on to fix the 1918 series between the White Sox and the Cincinnati Reds. There were suspicions that the 1914 series was crooked, too, especially as Sullivan took so many bets on Boston. They had been at the bottom of the National League as late as July 4 but ended up winning the series that October in a clean sweep, 4–0. Nothing was ever proved, though. Instead, Jay’s win was put down to his pluck. And perhaps that was right. “The man who studied the form, the scientific bettor, placed his money on the Athletics,” said the
Day
newspaper. “The man with the hunch was the one who cashed in.” Jay, they said, was a “daring bettor and operator in the market.”
    Let’s move in for a close-up. In the spring of 1915, Jay was spending his evenings at the San Souci club, in the basement of the Heidelberg building on 42nd Street. The star attraction there was a young dancer named Mae Murray, a short blonde with heavy eyelids and a thick, full mouth. She was soon to become famous throughout the world as the “girl with the bee-stung lips,” the brightest star at MGM. Back then she was, she insisted, an innocent little ingenue, trying to break out from the chorus lines on Broadway. Her chance came when Irving Berlin asked her to fill in for Irene Castle, the female lead in his production of
Watch Your Step
, which had opened a few weeks earlier and was still playing to full houses. “You’ve got to go on,” Berlin told her. “Irene is very ill. The doctors won’t allow her out of bed. You’ve got to help me.” He didn’t need to twist her arm. Murray was about to go on stage, but she cut out of the San Souci and skipped down to the New Amsterdam Theatre. She had four hours to get ready, time enough to get a costume fitted and