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