Authors: William Nack
Jockey Eddie Arcaro was riding Bold Ruler toward the winner’s circle late that afternoon of 1956, moments after the colt had raced to a two-length victory in the Futurity at Belmont Park, when Mrs. Henry Carnegie Phipps stepped forward to meet them. Bold Ruler had just beaten the fastest two-year-old colts in America, running in near-record time, and he was dancing home, his nostrils flaring hotly, his neck bowed and lathered with sweat, moving powerfully toward his seventy-three-year-old owner. Turfwriter Charles Hatton watched her meet him.
“Mrs. Phipps was out at the gap to get him and lead him down that silly victory lane they had there. And she must have weighed all of ninety pounds, and here is this big young stud horse—and she walked right up to him and held out her hand, and he just settled right down and dropped his head so she could get ahold of the chin strap, and Bold Ruler just walked like an old cow along that lane and she wasn’t putting any pressure on him to quiet him down or make him be still. It was one of the most amazing sights I’ve ever seen. It was incredible to me because anyone else reaching for that horse—and he was hot!—you’d have had to snatch him or he’d throw you off your feet or step all over you. But not with her. For her he was just a real chivalrous prince of a colt. He came back to her and stopped all the monkeyshines, ducked down his head and held out his chin, and here was this little old lady with a big young stud horse on the other end and he was just as gentle as he could be.”
Even growing old, as her walnut face withdrew inside a frame of white hair, she had a mind as quick as a crack of lightning and always drove to the racetrack in the morning by herself, without a chauffeur, steering her Bentley south from Spring Hill, the marble palace on Long Island.
Mrs. Phipps must have seemed the picture of some innocent eccentric—the way she tipped back her head to see the road above the dash, the way she gripped the wheel with both hands, the way she climbed from the car with the poodles beside her and walked into the barn at Belmont Park. Her horses turned to watch her coming. She carried sugar, and she wore a plain dress, sometimes a stocking with a run in it and sometimes moccasins or gym shoes. The men at work in the stables stepped gingerly around her when she walked up the shed, some nodding deferentially and saying hello, and she returned the salutations but did not speak at length to them, only to Sunny Jim Fitzsimmons, her crippled trainer.
On summer mornings they would sit as if enthroned like ancients from another time. He was the sage, a former trolley car motorman from Sheepshead Bay in Brooklyn who became one of the finest horsemen of all time, the only man to train two winners of the Triple Crown, Gallant Fox and Omaha, and almost three and four in Johnstown and Nashua. She was the patron, fulfilling the aristocratic role, racing horses for the sport of it and never complaining, win or lose. She was the stable bookkeeper and knew how much each horse had won. She would ask how they were doing, how they were eating, and when and how they were working, and when and where they would race again. She was an independent little statue of a woman who went her own way, and she would walk up to the shed and stop to pet and feed her horses, complimenting those who had won, scolding softly those who had just lost: “You dope,” she would say, holding a cube of sugar. “I don’t know if I should give you one.” But she always did.
She was the grande dame of the American turf, and she hardly ever spoke in public. The news accounts in words attributed directly to her are sparse, and one newsman confided that he always left her alone when he saw her sitting in the box seat because he sensed a privacy inviolate.
She was born Gladys Mills on June 19, 1883, in Newport, Rhode Island, a twin daughter of Ruth Livingston and Ogden Mills, her name minted from a marriage between heirs of two of the largest family fortunes in America. The Livingstons were old American wealth and aristocracy, pre-Revolutionary real estate and later steamboats up the Hudson. The Millses were nineteenth-century nouveau riche. Darius Ogden Mills made millions in the California Gold Rush. His son Ogden became a financier, and a sportsman. He went into a racing partnership with Lord Derby of England, and together they operated a strong stable of racehorses on the Continent—so strong that in 1928, the year Mills died, it was the leading stable in France. The Mills-Derby racing venture continued to endure when Gladys Mills’s twin sister, the Right Honourable Beatrice, Countess of Granard, replaced her father and helped to carry the stable. By then Gladys Mills was an owner, too.
In 1907, when she was twenty-four years old, Gladys Mills married into one of the wealthiest and most powerful families in America, the steel family of her husband, Henry Carnegie Phipps. He was a son of Henry Phipps, who, with Andrew Carnegie, founded a steelworks so profitable that when J. Pierpont Morgan bought them out in 1901, Phipps’s share alone came to $50 million.
Gladys Mills and Henry Carnegie Phipps settled down in New York, in a home with a marble facade at Eighty-seventh Street and Fifth Avenue, and on the Long Island estate off Wheatley Road in Roslyn. Phipps was tall, distinguished, and played polo. Mrs. Phipps was small, with a flinty New England dignity about her, and a crack shot. In her later years she climbed into a swivel seat mounted on a swamp truck in Florida, and shot birds with a 12-gauge as she spun in circles. She bagged her limit in quail at the age of eighty-six.
Mrs. Phipps, in partnership with her brother Ogden L. Mills and his wife, bought horses for the first time in the mid-1920s and raced them under the nom de course of the Wheatley Stable. The stable flourished early, launched to a quick success after the leading American breeder of the 1920s, Harry Payne Whitney, a Long Island neighbor of the Phippses, offered her a choice of ten of his yearlings in 1926, reportedly to satisfy a gambling debt incurred during a high-rolling card game with Henry Carnegie Phipps. Whether out of luck or shrewdness—probably part of both—Mrs. Phipps and trainer Sunny Jim Fitzsimmons chose five yearlings that went on to win stakes for her and more than once whipped Whitney’s horses. Incredibly, the other five were multiple winners, too, though not of stakes. The best of the ten were Diabolo, a long-distance runner who won the 1929 Jockey Club Gold Cup at two miles, and the unbeaten but ill-fated two-year-old Dice (who died of colic as a youngster), as well as Nixie, Distraction, and Swizzlestick.
Her passion was for horses purely as runners. “I just like to see them perform as thoroughbreds,” she once said, in one of her rare public remarks. Her interest in horses involved her as a breeder soon enough. In 1929, the same year Diabolo won the Jockey Club Gold Cup, she purchased a broodmare, Virginia L., in partnership with Marshall Field, who had just helped finance the importation of Sir Gallahad III. Mrs. Phipps never bought a farm of her own for the breeding and raising of thoroughbreds. But she did meet Arthur B. Hancock, Sr., early in her career as an owner, and when she finally did decide to breed as well as race her horses, she became a client of Hancock at Claiborne Farm. Through the next forty years, most of her homebreds were foaled and raised in Paris, Kentucky. It was she who decided which of her mares would be bred to which stallion; she became a student of the pedigrees of all her horses, and though she took advice, she made her own decisions.
In her first twenty-five years as a breeder, by far the fastest thoroughbred she bred was Seabiscuit, the bay horse who bumped off War Admiral in the famous Pimlico match race on November 1, 1938, though “The Biscuit” did not carry the Wheatley gold and purple silks for her then. He had raced eighteen times as a two-year-old before he won his first start for her, thirty-five times in all that year with only five wins. He was just a sluggish selling plater when Mrs. Phipps, becoming impatient and discouraged with him, sold him for $8000 to Charles S. Howard. It was one of the rare mistakes she made in the business. Seabiscuit retired in 1940 with earnings of $437,430, a world record at the time.
The Wheatley-breds won more than $100,000 for the first time in 1935, winning 106 races and $113,834. Never again did they earn less than $100,000 annually. Among the best horses Mrs. Phipps bred were Seabiscuit, High Voltage, and Misty Morn, a daughter of Princequillo who won $212,575. Yet nothing she ever did compared in import to the purchase she made early in the 1950s, when she prevailed upon Hancock to sell her Miss Disco, upon whom the Phippses founded a dynasty.
Miss Disco came to Gladys Phipps at the end of a curious, sometimes unlikely series of events that began unfolding late in 1933, the year Alfred Gwynne Vanderbilt turned twenty-one. Vanderbilt had just begun to involve himself as an owner and breeder of racehorses, as a man of name, means, and ambition in the thoroughbred industry. He grew up, fatherless, with family fortunes on both sides of his pedigree.
He was the son of Alfred G. Vanderbilt, Sr., a wealthy sportsman who perished with 1152 others when a German U-boat sank the
Lusitania
off the Irish coast, and the former Margaret Emerson, the daughter of Isaac Emerson, a Baltimore chemist of modest means until he invented Bromo-Seltzer. Emerson acquired Sagamore Farm, an 848-acre stretch of rolling landscape in the Worthington Valley, and his daughter went into racing. Young Alfred acquired his mother’s passion for the sport, dropping out of Yale at the end of his sophomore year to raise and race the running horse.
In the photos taken of him in the early 1930s, he looks strikingly like the James Stewart of
Destry Rides Again
, and what adds to that impression is the whimsy of his humor. One year, prior to the running of a race in which his horse appeared to have no chance, Vanderbilt gave jockey Ted Atkinson a sandwich, a wristwatch, and a flashlight, advising him, “It may be dark before you get back.” He never took himself too seriously, not even as a breeder.
When Vanderbilt turned twenty-one on September 22, 1933, he was given $2 million in government bonds, the first of four such installments his father had left him. His mother gave him Sagamore Farm, which Isaac Emerson had given to her. With that, Vanderbilt had money and land, the means to buy and breed and raise and race horses of his own.
In August of 1933, he hopped into his sporty new LaSalle roadster, fire-engine red, and tooled north toward Saratoga. Beside him in the car was a set of his new racing silks, a modified version of his mother’s silks of cerise and white blocks. On the advice of trainer Bud Stotler, he was heading north with a check for $25,000 to buy a big, raw-boned chestnut colt named Discovery. Vanderbilt intended to buy him and race him in the Hopeful Stakes. Discovery had been bred by Walter Salmon’s Mereworth Farm, and he was a son of a fast if fiery rogue of a horse named Display. Display was a son of Fair Play, who also sired Man o’ War, and there was nothing docile about “Big Red.” But when bred to Ariadne, Display transmitted nothing of his unruliness to their offspring, Discovery, a colt of estimable poise and calm at the post. He launched his racing career in a blaze of indifference, but by the time of the Hopeful Stakes at Saratoga, he had matured considerably.
The sale was delayed until after the Hopeful Stakes, so Vanderbilt didn’t get to run Discovery in the race. After the horse finished a sharp third in the event—behind High Quest—his price jumped from $25,000 to $40,000, the equivalent of $400,000 today. Vanderbilt left Saratoga without the horse, but he had been impressed by Discovery and continued following the colt’s career. He bought the horse when he had the first chance.
Discovery won eight of his sixteen starts as a three-year-old, including the Brooklyn Handicap against older horses. But even that hardly suggested what was coming when he matured to a four-year-old horse, 16.1 hands high and 1200 pounds, about 200 pounds heavier than the average horse. (A horse is measured from the ground to his withers, the highest part of his back, in a unit of measure called “hands”—a hand is 4 inches, so Discovery at 16.1 hands stood 65 inches from the ground to the withers.)
Though Discovery lost his first five starts as a four-year-old, he came alive when he broke from the barrier in the Brooklyn Handicap in June and carried 123 pounds for a new world’s record for a mile and an eighth, 1:48
1
/
5
, the second year he won the race. And for the next six weeks, until August 10, Discovery rolled across the east and midwest in a boxcar on what remains among the greatest six-week grinds in racing history. As a horse running mostly in handicaps, Discovery had to carry whatever weights the track handicappers decided to load on him. The aim of handicapping horses with weights (inserting lead slabs in the jockey’s saddle) is simply to weigh down the horses—with the superior horses carrying more than their inferiors—so that all finish at the same time, in a dead heat. That is the theory, anyway. Discovery, a sensible horse, never paid any attention to that theory.
After the Brooklyn, he won the Detroit Challenge Cup carrying 126 pounds and then the Stars and Stripes Handicap in Chicago, spotting his rivals’ weight and winning by six. He kept winning with high weights everywhere.
Known as the “Iron Horse” and the “Big Train,” Discovery retired after the 1936 season with a lifetime record of sixty-three starts—twenty-seven wins, ten seconds, and ten thirds—and with a reputation as one of the greatest weight carriers that ever lived, a touchstone by which other handicappers would be measured. Vanderbilt sent him to Sagamore for stud duty beginning in 1937.
“There is no other horse in the entire range of turf history, American or foreign, that ever attempted to do anything so tremendous or came anywhere near Discovery to doing it so successfully,” wrote turf historian John Hervey.
Vanderbilt, for his part, did not confine his activities to racing during his first years as an owner. He was buying mares at auction to build up breeding operations. The most crucial purchase he ever made at a sale occurred at the dispersal sale of W. Robertson Coe in 1935, when a mare named Sweep Out was led into the sales ring. The mare was in foal to Pompey, a fast and game horse who won the Futurity Stakes at Belmont Park in 1925.