Alfred Sr. and Margaret Emerson were married to other people when they met in 1908 at the Plaza Hotel in New York, where Alfred Sr. had a permanent suite. Margaret’s husband was the doctor on her father’s yacht, but he was also an alcoholic who beat her, and she divorced him, claiming cruelty. (He knocked her out and put her on an eighth-floor window ledge at the Plaza one night; fortunately, the night air revived her and she rolled back inside instead of off the edge.) Alfred Sr.’s marriage also ended in scandal after his affair with Agnes O’Brien Ruiz, the wife of Cuba’s attachÉ in Washington; his divorce cost him a reported $10 million. Ruiz committed suicide when Alfred Sr. took up with Margaret, but the scandal eventually subsided and Alfred Sr. and Margaret were married in 1911.
Margaret, heiress to the vast Bromo-Seltzer fortune, was a strong, restless woman. Dark-haired, opinionated, and self-sufficient,
she rode expertly, beat all comers at croquet, won skeet-shooting contests on the Riviera, and had circled the world on her father’s yacht several times. Fond of horses, she was a perfect match for Alfred Sr. They quickly had two sons: Alfred Jr., born near London in 1912, and George, born two years later. Their life seemed idyllic.
On May 1, 1915, in New York, Alfred Sr. boarded the Lusitania, a luxurious British steamship, bound for a meeting of the International Horse Show Association in England. He was looking forward to a week of caviar, cocktails, and conversation on board, and like most of the almost two thousand passengers, had paid little attention to a warning from the German government: “Travelers are reminded that a state of war exists between Germany and her allies and Great Britain and her allies; that the zone of war includes the waters adjacent to the British Isles; and that… vessels flying the flag of Great Britain, or any of her allies, are liable to destruction in those waters.”
Days later, the Lusitania steered right through the “zone of war” off the Irish coast instead of charting a more evasive route, and a German U-boat captain fired a torpedo that hit the Lusitania and sank it. More than seven hundred passengers survived, but Alfred Sr. drowned after handing his life vest to a woman and suggesting that the men endeavor to “save the children,” an act that, the New York Times wrote, “gave expression to the whole modern idea of civilization.”
It was a noble death, but it tore a devastating hole in the ornate tapestry of the Vanderbilt dynasty. The family fortune soon began to shrink, carved up by a wicked scythe of taxes, marriages, children, divorces, the end of the railroad monopoly, and the failure of future generations to continue making money.
Alfred Vanderbilt Jr. was two years old when the Lusitania went down. Although his father’s will generously stipulated that he receive $5.87 million in government bonds, with the principal and accumulated interest to be paid in four installments as he grew into adulthood, he had lost his father. “His childhood was a lonesome one,” the Associated Press reported in a 1936 profile of Vanderbilt. “Surrounded by luxury in houses full of servants, he had little company.
His health was always delicate, and usually there was a nurse hovering with physicians making frequent calls.”
Margaret remarried in 1918 to Raymond Baker, the head of the United States Mint. (She was now known as Margaret Emerson McKim Vanderbilt Baker and maintained a residence in Nevada for facilitating divorces.) Her boys, growing up without their own father, increasingly turned to her father as a paternal influence. Captain Emerson, as he was known, was a mustachioed yachtsman and world traveler with a $20 million estate. Margaret was the love of his life—his yacht was named after her—and he doted on her children.
On a trip to Baltimore in 1923, Margaret took Alfred to see the Preakness Stakes, one of the biggest events in racing. They watched the races from the Old Clubhouse, the Victorian manor overlooking the head of the stretch, and Alfred, at age ten, cashed a winning bet on the Preakness. His horse, Tall Timber, finished fifth but was coupled with the winner. “The excitement of being allowed to eat a hot dog with mustard, most of which ended up on my lapels, was forgotten when I saw the horses and the bright silks of the jockeys coming down the stretch. I never got over that feeling,” Vanderbilt wrote years later in a Daily Racing Form essay.
Margaret had never seen Alfred so excited, and within months, she had bought a steeplechase horse, partly to appease him. After winning several races with the horse, she decided to follow the lead of other society families and back a full-fledged racing stable. She hired a broad-shouldered, no-nonsense trainer, Joseph “Bud” Stotler, who made some purchases at the Saratoga sales. She named her outfit Sagamore Stable—a sagamore was an Indian tribal chief—and Margaret’s sprawling wooded retreat in the Adirondack Mountains, which she had inherited from Alfred Sr., was named Sagamore Lodge. Her silks were cerise and white in a pattern of blocks; Alfred Sr.’s coaching colors had been red and white, and cerise is a vivid purplish red.
Sagamore Stable experienced instant success when a two-year-old colt named Rock Man won the Incentive Stakes and Nursery Stakes at Pimlico in 1925. As a three-year-old the next spring, he had the lead in the Preakness after a half mile and trailed only one colt entering the stretch before fading. Disregarded at 42-1 odds in the Kentucky Derby five days later (before World War II, the Derby was sometimes run after the Preakness), Rock Man pressed the leaders up the backside and into the homestretch before tiring. He finished eight lengths behind the winner but stuck his neck out for third.
Another Sagamore colt, Lord Chaucer, showed even more promise as a two-year-old in 1926, winning the Hopeful Stakes at Saratoga. Pointed for the classics the next spring, he was running third and taking the measure of the leaders on the turn of the Pimlico Futurity when he collided with a rival and tumbled to the dirt. His leg broken, he was humanely put to death.
The stable thrived, recording forty-six wins and more than $125,000 in earnings in 1926 and 1927. Three years after its inception, Sagamore was one of racing’s top fifty outfits. Sensing his daughter’s excitement, Emerson came up with an idea. Long entranced by the rolling limestone hills north of Baltimore, where he owned a summer estate, he purchased a 250-acre tract from a farmer and gave it to Margaret with plans to turn it into a horse farm for her stable. He would spend $500,000 on indoor and outdoor training tracks, a barn with fifty stalls, two paddocks, and housing for workers. Privately, he hoped the farm—to be named, naturally, Sagamore Farm, after the racing stable—would lure his daughter to Maryland more often.
Within months, the farm was bustling with grooms and exercise riders as the barns, paddocks, and racing strips were built. Another three-year-old ran well for Sagamore in 1928, a colt named Don Q. who finished well out of the money as one of eighteen starters in the Preakness, then ran seventh among twenty-two starters in the Kentucky Derby. By the end of the year, Margaret’s horses had won twenty-one races and she had divorced Raymond Baker and within twenty-four days married her fourth husband, Charles Minot Amory, a Harvard graduate from Boston society.
The stable’s rise matched young Vanderbilt’s growing interest in racing. He followed his mother’s horses in the newspapers and, school vacations permitting, by her side, and traveled with her every August to Saratoga, where he spent mornings at the barn, afternoons at the races, and evenings at dinner with racing’s upper crust. He sat for hours with Colonel E. R. Bradley, the master of Idle Hour Farm, learning from one of the nation’s eminent breeders and horse owners; Bradley later sent him racing books and magazines, solicited his opinions on equine matters, and offered a free stud service to his first mare. Bud Stotler also spent many hours with the young man, answering his many questions around the barn and during the races.
During the school year, Vanderbilt arranged to receive the Daily Racing Form at St. Paul’s, the boarding school he attended in Concord, New Hampshire; the paper came in the mail in an unmarked envelope to prevent the deans from suspecting his mind might not be on his studies. He read it under his bedcovers, by flashlight, after lights were out; his mind was, indeed, distracted. He ran
an annual betting book on the Kentucky Derby, cashing in big in 1929 when none of his classmates backed the long-shot winner, Clyde Van Dusen.
In the late 1920s, Margaret let him make some breeding decisions and pick out several yearlings and follow them as if they were his own. One won a stakes race at Aqueduct, and when another won at Saratoga in 1928, the local newspaper labeled Vanderbilt, fifteen, as “the youngest owner on the American turf.” That he would follow his mother’s lead and have his own racing stable was already apparent.
He used his allowance money to buy his first horse in August 1931, just before starting at Yale. He slipped away with Stotler one night at Saratoga, went to the yearling sales, and came home with a smallish chestnut filly that had cost $250. The filly, which he named Sue Jones—a dull name not up to the high standard of cleverness he later set—joined Margaret’s stable and debuted on June 16, 1932, at Aqueduct, finishing third. The Blood-Horse, a prominent racing industry journal, noted the debut of young Vanderbilt’s silks, which incorporated the same cerise and white colors as Margaret’s, only in a pattern of diamonds instead of blocks.
Plainly more interested in racing than literature or economics, Vanderbilt lasted just three semesters at Yale before dropping out. “I believed I had discovered what I wanted in life, and I was right. I wanted racetrack,” he later told interviewers. Conveniently, Margaret was tiring of the expense of keeping the farm and stable running, especially after her father died in 1931. Emerson’s will stipulated that Margaret pass the farm on to Alfred when she died, but she decided to step up the timetable and give it to him when he turned twenty-one.
It is doubtful anyone in America celebrated a more bountiful or conspicuous birthday in 1933. At the lowest ebb of the Great Depression, Vanderbilt received from his mother Sagamore Farm and a racing stable, a burnt-gold Rolls-Royce, and the lifelong services of valet Louis Cheri. From his father’s estate, he received more than $2 million, with three similar payments scheduled for his twenty-fifth, thirtieth, and thirty-fifth birthdays. The New York Times noted in an article that another Vanderbilt scion had “reached his majority”—turned twenty-one—and was planning to devote his money and time to racing thoroughbreds.
“I went to the races with Margaret once at Hialeah, and she enjoyed it immensely, but Alfred wanted it to be his own show, and she graciously gave him the stable,” his friend Clyde Roche said. “For her, it was a circle of people who knew each other and enjoyed the racing setting, but I don’t think she had a devotion to it. Alfred certainly did.”
Looking for horses to improve the stable, which had sagged, Vanderbilt focused on a big, heavy-looking two-year-old named Discovery. Sired by Display, a Preakness winner nicknamed the Iron Horse, Discovery was owned by Walter J. Salmon, a New York financier who, looking to cut costs, had leased the horse to Adolphe Pons, a horseman whose father had immigrated from France and become associated with the Belmont family. Salmon wanted Pons to sell Discovery.
Stotler began negotiating a price after seeing Discovery win a race, and Vanderbilt, thinking the deal was done, put his silks in his car and drove to Saratoga, expecting Discovery to run for him in the Hopeful Stakes. Instead, Salmon and Pons elected to let the horse run in Pons’s colors once more, then called off the deal when Discovery ran third, raising his value. After several more months of negotiations, Vanderbilt offered $25,000 and left on a four-month hunting expedition in Africa. He had been at sea for a day when he received a simply worded telegram from Stotler: “Discovery yours.” It would be the most important equine purchase of his life.
In Africa, Vanderbilt bagged a lion and several elephants, was chased by a rhinoceros, fished with Ernest Hemingway, and met Beryl Markham, the female aviator. Upon returning, he jumped excitedly into the business of running a farm and a stable. His hunger for knowledge was so intense that Stotler utilized him as an assistant trainer even though he was the boss, dispatching him to small tracks to run minor horses, a seemingly thankless job Vanderbilt relished. He ran the stalls and established a rapport with the other men on the backstretch, asking for no favors and insisting that he be called Alfred or Al.
Discovery ran well enough in the spring of 1934 that Vanderbilt took him to Louisville for the Kentucky Derby. Sent to the post at 12-1 odds, he took a three-length lead into the stretch as jockey Johnny Bejshak furiously worked him. Pandemonium reigned in Vanderbilt’s private box. Although Cavalcade rallied to win, Discovery finished second, and Vanderbilt never forgot the sensation of holding a lead so late in America’s greatest race. Discovery eventually recorded several major wins that year, but he was known more for losing a series of races to Cavalcade.
Racing as a four-year-old in 1935, Discovery had lost five in a row in the spring and was being dismissed as a disappointment when “all of a sudden, he got good,” Vanderbilt recalled in a Thoroughbred Times interview in 1993. He won eight straight stakes races in seven weeks in New York, Chicago, Boston, and Detroit, setting several track records while enduring an exhausting schedule of train rides. By the end of the year, the horse known as the Big Train had traveled nine thousand miles and won eleven stakes races at eight tracks, with handicappers asking him to carry as much as 139 pounds. It was a remarkable performance, and Vanderbilt was acclaimed for his willingness to run the horse anywhere against anyone under any conditions.
Vanderbilt’s stable finished 1935 with more than $300,000 in earnings, tops in the nation, and thirty-seven stakes wins, the most by any stable in twenty-five years. Less than two years after taking over, Vanderbilt was at the top of the game along with Belair Stud, C. V. Whitney, Brookmeade Stable, and the rest of racing’s ruling class. He purchased a neighboring farm to double the size of Sagamore Farm and spent lavishly to turn it into a showcase. “When he came in for a visit, we all lined up, like a military greeting,” Claude Appley recalled. “He knew the breeding of every horse in the field, and we had a lot of horses. He was an encyclopedia.”
It was inevitable that he would become more involved in the racing industry. Vanderbilts seldom lingered on any sideline for long, and anyone with his enthusiasm and financial wherewithal belonged in racing’s hierarchy. The success of his stable led the Maryland Jockey Club, which operated Pimlico, to give him a seat on its board of directors in 1936. Soon, when the board was deciding whether to take out a liquor license—snobbish Pimlico had previously abhorred the idea—Vanderbilt, a nondrinker, cast the tie-breaking vote in favor of alcohol, believing it would draw more fans to the track. Pimlico’s vice president resigned, and a longtime secretary announced that his stock in the track was for sale. “I’ll buy it!” Vanderbilt roared. Before long, he had purchased a controlling interest of Pimlico stock and was running the track as its president.
As his vote for liquor indicated, Vanderbilt had strong and unconventional ideas about tracks and racing. He was, at twenty-five, a maverick, even though he was a member of high society. He believed that racing had been run for the sake of its wealthy old guard for far too long and that the interests of the average fan had been ignored. There was too much emphasis on betting, he felt, and not enough on making the race-day experience interesting for the customers. In general, he believed, an infusion of spirit and innovation was needed.
“He was, as we’d say today, a guy who thought ‘outside the box,’ ” said Tim Capps, a Maryland-based racing author, historian, and executive. “He was an iconoclast Didn’t fit the genre of the ‘old money’ crowd. He operated outside the framework of what people thought third- or fourth-generation money ought to be like. He had a sense of what the fans wanted. He understood the value of promotion. He was willing to take chances.”
At Pimlico, which had been losing money and fans, he increased purse sizes and inaugurated new races such as the Pimlico Special, intending to attract better horses and give fans at least one stakes race every day. He installed a public-address system, teletimers, cameras, and a starting gate with closed doors, the first on the East Coast Most famously, he spent $58,
000 to remove the hill in the infield that had given the track its nickname, Old Hilltop. Some saw the mound as historic, and many old-timers were aghast, but fans had complained that they couldn’t see their horses run, and away it went “He was the only guy who wanted to protect the public to the extent he did,” longtime California steward Pete Pederson said.
A hands-on boss, he demanded high standards from his employees and made sure those standards were met. “He would get up one day and not shave, not wear a tie, wear a sport shirt, and go to the track unrecognized,” Alfred Vanderbilt III said. “The next day, there would be hell to pay. He knew which pari-mutuel clerks had been rude, what was and wasn’t getting done, and what needed to be done.”
Pimlico experienced a rebirth, drawing better horses and larger crowds. “It was my theory that if the product was right, everything else would take care of itself, and that was how it worked out attendance picked up, business picked up, the net profit picked up and the prestige picked up,” Vanderbilt told Sports Illustrated in 1963. Impressed with his progressive management, as well as his commitment to racing, the Jockey Club made him its youngest-ever member in 1937, when he was twenty-five.
The Associated Press had labeled him “one of the most eligible bachelors between Bar Harbor and Palm Beach” in 1936 and asked in a headline, “How Long Till Vanderbilt Weds? Society Wondering.” He had courted a coterie of women in society, the theater, and the movies. Then he began dating Manuela Hudson early in 1938. She was the daughter of a San Francisco attorney and the niece of Charles Howard, who owned Seabiscuit, the most popular horse in America. Vanderbilt and Manuela met at Santa Anita, married in the summer of 1938, had a daughter named Wendy, bought a thirty-room house in New York, built another home overlooking Sagamore Farm—then divorced in the early 1940s.
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