by Andy Bull
And that was when it happened. C. H. Bell, riding Gold Van, bolted up the inside and beat him to the fence. The two horses clashed as they landed on the other side, and Kersey was forced wide. He swerved way off the racing line—off, in fact, across the course. The shouts of encouragement became screams of panic. Jay tried to rein back, but it was too late. He had lost control. The close-packed crowd scattered as his horse burst through the row of flags that marked the edge of the track. Gowns billowing, hats flying, they raced for the safety of the traps and carriages arrayed around the outfield.
Jay forced Kersey back onto the track and whipped the horse hard into a hot finish. But he was way back when Gold Van broke the tape. Jay was still seething at the presentation ceremony. He cursed under his breath as he watched Bell receive the trophy, and again out loud when one of the patrol judges hurried up to tell him he was officially disqualified. A few kind words from Virginia Vanderbilt soothed his wounded pride. She said that the race was “the most sensational of the day,” and the sweet smile she shot him as he spoke almost made it all seem worthwhile. Jay’s friends always said that few things mattered to him more than winning. Pretty women were one of them.
Jay O’Brien grew up rich. He was born in New York on February 22, 1883, and enjoyed all the privileges his father had worked so hard to earn for his family. Miles O’Brien had emigrated from Ireland in the 1860s. His parents had wanted him to take a career in law, but instead he traveled, alone, to New York. He got a job as a clerk at H. B. Claflin & Co., a wholesale dry goods retailer in downtown Manhattan. But Miles was bound for better things. He worked his way up to the top of the company, and on the way he became a leader of the Fenian society Clan na Gael and an active member of the Irish Parliamentary Fund Association, which supported the campaign for home rule. An enlightened, compassionate man and a prominent independent Democrat, he moved into public service. When his friend William Russell Grace became the first Irish-born mayor of New York, he brought O’Brien up with him. He appointed him to the city’s board of education. There, Miles campaigned against overcrowding in classrooms and called for the introduction of school baths and free lectures for adults. He became president of the board in 1900.
If that all sounds a little too clean for a man who successfully negotiated his way through the cut-throat world of Irish-American politics in late-nineteenth-century New York, there are hints of shadows in Miles’s story too. He certainly had his tangles in Tammany Hall, the Democratic society that controlled politics in New York City and State from the 1790s on. Tammany relied on support from the Irish immigrant community, and Miles was one of many men the society helped gain a foothold in American politics. By his time, it was infamous throughout the city for its corruption, graft, and internecine squabbling. In 1883, Miles was accused of being one of the organizers of the Fenian dynamite plot. He denied all involvement and told the Boston Herald that he was opposed to dynamite—that he believed “constitutional agitation” was the way to overthrow British power in Ireland. Then, in 1889, he was caught up in a minor scandal when two friends of his fell out over dinner and one challenged the other to a duel. They kept that out of the papers, but Miles was exposed twelve years later when his son Thomas, Jay’s younger brother, was arrested for disorderly conduct. The boy was released without charge the next day, but the matter was muddied when the arresting officer reported that Miles had threatened him outside the courthouse. “Can I do anything for you?” the policeman had asked. “No,” O’Brien had replied. “But I will do something for you. I’ll cause you to lose a good deal of sleep over this matter. You’ll not stay at the 100th Street station very long, you’ll be transferred.” O’Brien insisted that the story was “made out of cloth,” an “utter fabrication.” The precinct’s commanding officer agreed with Miles, but that didn’t necessarily do much to dispel the idea that he had the local police in his pocket. O’Brien owned an entire block of the Bronx, and by the time he died in 1910, he was president of the Bank of New Amsterdam. No doubt he drew a lot of water.
Jay was raised in his father’s image. He had a quick temper and contempt for authority. He was used to getting his own way. He’d first learned to ride during his summers in Long Branch, New Jersey, on a horse his father bought for him. He was strictly amateur. Did it for the fun and the glory. At first the courses he rode were all up in Long Island. The race that had so thrilled Virginia Vanderbilt took place at Gracefield, the private estate of the former mayor and an old friend of his father’s, William Grace. The news reports of the races in the papers paid more attention to the people than the horses and always included long lists of the luminaries who had been in attendance. Despite what happened that day at Gracefield, Jay was an excellent jockey. In November 1906 he won four races in a single afternoon at Huntington, two on the flat and two over the jumps. He would have won the fifth, too, if he hadn’t fallen head over heels as he came over the first jump on the second lap; he leaped up, remounted, and made for the finish, but came in fourth. “A small but select group” was there to see him do it. In 1907 he moved up a notch: he started to enter races at the great tracks of Saratoga and Belmont, where crowds of more than ten thousand filled the grandstands. He didn’t fare well. He took a bad fall at Saratoga while urging the nag he was saddled with over the steepest jump on the course, and was whisked away to hospital in an ambulance. He fell again while riding the favorite at Sheepshead later that summer, breaking a bone in his leg.
After that he began to get a reputation as an unlucky jockey. Truth was, he was taking too many risks. But that was more than half the fun. If there was nothing at stake, Jay lost interest. At Baltimore he gave up when well beaten. He was easing toward the finish when he was overtaken by a horse he had thought was far behind him. The stewards suspended him because of his “carelessness,” suspecting he had thrown the race for second place. Characteristically, Jay protested the decision to the National Steeplechase and Hunt Association, which not only upheld the decision but also stripped him of his license to ride as an amateur jockey. Piqued, he drifted away from racing. He gave it up altogether when a horse he owned, but wasn’t riding, fell during a race at Saratoga. It landed on a rival jockey and crushed him to death.
Not for the first time, Jay left one passion behind him and pounced on another. He had studied law at Princeton, and he dabbled in stocks and bonds for H. L. Horton. But honest work didn’t interest him much. All the time he had spent at the track had given him a taste for gambling. His game was baccarat, though, in the words of his first wife, “he would bet on anything under the sun.” In 1913 he took a holiday in England. He sailed back to New York on the Mauretania, the largest, fastest ocean liner in the world. Jay spent the voyage holed up in the smoking room, playing cards. By the time the ship docked in New York, he had won twenty-five thousand dollars, almost half of which was made in the final twenty minutes of the voyage as his desperate opponents tried to win back what they had lost in a frantic final game. Word spread around the ship that something extraordinary was afoot in the smoking room, which was soon filled with spectators. They were keener to watch the cards than they were to take in the sight of the city from the deck. It was worth it; Jay won five thousand dollars on the turn of a single card. This caused whispers. Someone muttered the phrase “card-sharping” to the press, but nothing came of it.
Jay had another narrow escape later that same year. He and his friend Al Davis had hired a bachelor pad above Murray’s Roman Gardens, the most famous of the ritzy “lobster palaces” that popped up on the Gay White Way of 42nd Street. Downstairs at Murray’s they had a rotating dance floor, which turned lazy circles underneath a ceiling filled with electric stars. Showgirls flitted in between the statues and fountains and took turns dancing tangos with the clientele. And if any of the guests found all that to be insufficient entertainment, well, the showgirls would show them upstairs to Jay and Al’s apartment, where there was what one journalist called “a wonderfully circumspect roul
ette wheel” ready and waiting for anyone who was rich, drunk, or dumb enough to take the chance. Until they made the mistake of taking twenty-five thousand dollars off a staff member of the Russian consulate. He woke the next morning with a thick head and a slim wallet. Incensed, he reported Jay and Al to the police. He said he had been fleeced.
And so he had. They called the con “shearing the lamb.” The showgirls, who took a cut of the profits, were paid to spot victims, liquor them up, and lead them to the suite. Then they lured the mark into splashing his cash on the crooked roulette wheel. Astonishing sums were lost at that little gaming table. Angier Duke, who was then a trustee of Duke University, was forced to issue a public denial that he had dropped eighty thousand dollars there. He admitted, a little coyly, that he had met Jay in Murray’s, but insisted that he was “just very fond of music and dancing” and had dropped in at the club to “tango away a little time.” Snaring and shearing a foreign diplomat, though, was just asking for trouble. Unlike Angy Duke, he wasn’t about to let them off easy.
Deputy Commissioner of Police Newburger led the raid himself. He and his men hustled into Murray’s and busted down the door to the suite. But Jay had been tipped off. The room was empty, except for one little roulette table. They picked it up and carried it away, past the replica of Cleopatra’s barge, the thirty-foot marble fountain, and out through the restaurant. “Tumult reigned among the gay throngs clustered in horrified bewilderment,” read one report. “Certain attractive girls professed to have no idea what it was all about. Others nudged their companions and winked significantly.” It took Newburger a couple of days to track down Jay and Al. They turned up in “another Broadway trottery” and were brought in for questioning, then charged with gambling. Jay insisted it was a “frame-up” and that the police were being used by two men who owed him money. The charges were eventually dismissed. But then, Jay had some low friends in high places. His thousand-dollar bail was paid by Arnold “Ace” Rothstein, one of the biggest racketeers in the city.
They called Rothstein “the 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 took her 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 rehearse a few steps with Irene’s husband and dancing partner, Vernon Castle, while Berlin accompanied them on a piano.
She was a sensation. The New York Times reported that she made “a decided hit and received round after round of applause.” Vernon Castle told her, “It’s all for you, Butterfly,” and dragged her out on stage to take a bow. “Vernon and I formed an unbreakable bond during that exciting, hectic, never-to-be-forgotten night,” Mae recalled. “It was the bond of rhythm lovers.” (Irene Castle, it has to be said, never really warmed to Mae. Not that Mae minded.) She took a cold shower and a quick supper, then raced back to the San Souci so she could perform there. After her number she received her second standing ovation of the night, the applause ringing on long after her encore. She slipped backstage to change into a long white gown, then stepped out into the club. She accepted a white gardenia, refused a glass of champagne, and fell into conversation with a man named Jack de Saulles.
De Saulles was thirty-seven, a real estate broker. He had been a star quarterback at Yale back in 1901, and was named that year in the New York Post’s All-American Team. He swept his arm around Mae’s shoulders.
And then she saw him, walking toward her from across the room. “A striking man, about 36, with dark, svelte hair, dark eyes, very well-groomed. He looked as if he had just been released by his valet. His white dress shirt gleamed with pink pearl studs.” Jay O’Brien. Mae couldn’t take her eyes off him.
Jay explained that he had been at the New Amsterdam Theatre that night and had watched her dance with Vernon Castle. And though she thought him fresh, she found she was “strangely grateful” for his praise. At that moment, she said, it felt “as though there were only two of us in the room.” De Saulles, understandably, seemed displeased with the interruption. Mae, who could surely have made a living writing penny romances if she hadn’t been blessed with so many other talents, remembered that she looked into Jay’s eyes and thought how “lustrous and dark they were,” then wondered to herself, “What is he like behind that white-white shirt, behind those pearls?”
De Saulles moved to turn her toward the dance floor, but Jay took de Saulles’s arm, lifted it from her shoulders, and slipped his own around her waist. “I bet I would dance with her tonight,” he told de Saulles as he led her out into the crowd. She assumed he was joking. He wasn’t. Later de Saulles, whose young Chilean wife was also there that evening, tried to persuade Mae
to let him take her home. She refused, and he explained to her, “Look, Jay and I have a bet on. He’s already won once from me tonight. Now you help me win over him.” He and Jay were pals; but then, as he commented to Mae a little later, “no men are friends where a woman is concerned.”
Jay was, Mae said, a glorious mover. “Our timing was so perfect that I could not speak,” she gushed. “I closed my eyes and wondered if all this night had been a dream.” Some of it might have been. “I looked up into his immobile, finely chiseled face and saw it registered no expression. It had the perfect proportions and even features of a statue. The only difference, I thought, was that I could see a muscle throb in his right jaw.” She gasped. Her heart skipped a beat. “Although this man was many years older than me”—all of two years, to be precise—“the attraction was undeniable.” As they turned across the floor, stepping together in time to the band, Jay, one eye on his bet with de Saulles, told her, “Don’t go away from me, because I tell you I am going to take you home.”
It wouldn’t quite be right to say that Mae fell for Jay that night. She said she found herself both repelled by and attracted to him. She thought he was typical of “the wealthy play crowd, who lived on inheritance,” and part of her “wanted to get away from these people whose lives seemed to be made up of betting, of intrigues, of matching wits.” Best to take that with a little pinch of salt. She also insisted that she kept asking herself, “What do these men want from me?” Was it “her charm, her natural sweetness?” Was it her newfound “success and acclaim?” Or was it something else altogether? Well, quite.