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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.

Vanderbilt bought her for $2000, and the following year she had a filly foal by Pompey that Vanderbilt named Outdone. In 1943, he bred Outdone to Discovery for the third time. She produced a good-looking filly foal in 1944. In fact, they were a grand bunch of foals at Sagamore that year, but Vanderbilt was not there to tend or race them. He had joined the navy in 1942 and was in command of a PT boat in the Pacific. While there, he instructed his farm manager and trainer to “go to the field and pick out twelve yearlings you like best, before they’re broken, and sell the rest.” Of the yearlings kept, none went on to any distinction either at the racetrack or in the stud. But of the twelve they sold, six eventually won major stakes races. One was Conniver, a daughter of Discovery, who was voted the leading handicap mare of the year in America in 1948. Another was the bay filly by Discovery from Outdone.

Sidney Schupper, not a major owner, bought the filly for $2000 and named her Miss Disco. Schupper raced her from 1946, when she was a two-year-old, until 1950, when she was six. She was a strikingly handsome, racy-looking mare with a beautiful head—a prominent forehead and the face penciled like that of an Arabian. She carried herself elegantly and liked to get her work done in a hurry. She won ten of fifty-four races and $80,250 for Schupper. Nor did she shy away from tangling with the boys. Miss Disco won the Interboro Handicap as a four-year-old, whipping colts over three-quarters of a mile, a sprint. She also won the New Rochelle Handicap. As a three-year-old, Miss Disco won the Test Stakes at Saratoga, a race in which a number of good fillies have run, if not won, over the years.

Miss Disco had speed, and she would transmit it to her many foals, one by one, especially the seal brown bay colt she foaled in 1954. Schupper did not own her then, not when she served in the stud.

At the close of Miss Disco’s racing career, Bull Hancock saw the potential in her as a broodmare, so he bought her from Schupper for himself, privately, for an undisclosed price. Bull had the Vanderbiltbred mare shipped to Claiborne Farm to join the bands of other mares. That was in 1950, when a rebirth at Claiborne Farm was in the making, and when Gladys Phipps prevailed upon Bull to sell the mare and he gave in, since she was an old client and wanted to own Miss Disco so badly.

Owned by Mrs. Phipps, the bay daughter of Discovery was bred to Nasrullah in 1951, and the following year she foaled a bay colt that Mrs. Phipps called Independence, a horse who would become one of the nation’s finest steeplechasers. Miss Disco was returned to Nasrullah in 1953, and in the spring of 1954 the whirlwind came, the horse for which all breeders tap their feet and wait.

The evening of April 6, 1954, at Claiborne Farm was perhaps the most remarkable of any in the long history of the American turf, certainly in the annals of Claiborne.

In the foaling barn set back off the road that winds through the farm, two foals were born that night thirty minutes apart. One was a bay son of Princequillo out of a mare called Knight’s Daughter. His name was Round Table, and by the time he retired as a racehorse at the end of 1959, running for Oklahoma oilman Travis Kerr, he had won forty-three of sixty-six races, been named America’s Horse of the Year in 1958, become regarded as the greatest grass runner in American history, and won more money than any horse in the history of the sport, $1,749,869.

Down the row of stalls Miss Disco gave birth to her son of Nasrullah who, by the time he retired in 1958, had been voted America’s Horse of the Year in 1957, won twenty-three races and $764,204, and earned a reputation as a magnificent cripple—one of the fleetest runners the American turf had ever known, and one of the gamest and most generous of horses. He was Bold Ruler.

Bold Ruler had a hernia as a foal, and he was so common looking that Hancock sequestered him in a distant paddock so that visitors to Claiborne Farm wouldn’t see him.

“He was a very skinny foal,” Hancock would recall. “We had the devil’s own time trying to get him to look good, and I was never really pleased with his condition the whole time I had him. But he had a good disposition in many ways and he never missed an oat.”

Bold Ruler suffered a painful accident as a yearling, almost cutting off his tongue in his stall one night, and the experience made him forever sensitive about his mouth. Nor was that all. One morning, while being broken under saddle, he fell and got tangled under a watering trough, almost breaking a leg while struggling to his feet. Somehow he survived all this, and made it to Hialeah Race Course in the winter of 1956. One of the first things he did was to begin ripping off quarter-mile sprints in 0:22 during morning workouts. Few quarter miles are run that fast in actual races.

So Fitzsimmons had no trouble cranking up his speedball for his first start at Jamaica on April 9. He won it by three and a half lengths. “Easy score,” reads the official past performance charts.

With that began the racing career of the fastest of all Nasrullah’s sons or daughters, a tall and leggy runner with a seal brown coat, phenomenal powers of acceleration, and a fiercely combative instinct that held him together when the oxygen was running low. Nothing ever seemed ready-made for him, nothing as easy as it might have been. There was always a measure of adversity to overcome, some trouble plaguing him. He raced three years, and at one time or another he was hounded by arthritis, by torn back muscles, and by what was called a “nerve condition” in his shoulder. A minor cardiac condition came and went during his three-year-old year. He developed splints—bony and sometimes painful growths on his legs—and later osselets, an arthritic condition in the ankle joint. He once wrenched an ankle. And throughout the last year he raced, when he won five of seven races and $209,994, he ran with an undetected two-and-a-half-inch bone sliver sticking into a leg tendon like a splinter. Bold Ruler carried 134 pounds in the mile-and-a-quarter Suburban Handicap of July 4, 1958—one of the epic duels of the turf—spotting the talented Clem 25 pounds. Bold Ruler did not take the lead early in the race, but then bounded past Clem after a half mile. Clem stalked him from there as they raced for the far turn. Banking for home, Bold Ruler was two on top. The crowd grew deafening as Clem moved up on Bold Ruler down the lane, charging on the outside and actually getting the lead at one point in the stretch. Most horses, losing such a lead, would have hung or quit. But jockey Eddie Arcaro dug in and Bold Ruler battled back, getting up just in time to win it by a nose.

He was almost rheumatic in the way he walked from his stall in the morning, but he was capable of tremendous speed, of dazzling bursts. In 1957, his three-year-old year, after spending the winter at Hialeah and Gulfstream Park trading blows with Calumet Farm’s Gen. Duke—perhaps the fastest horse Calumet ever produced, though he died before he could prove it—Bold Ruler came north to New York for the Wood Memorial on April 20 at Jamaica. The close of the race was an eyepopper, something like the Suburban a year later, with Bold Ruler and Gallant Man in a desperate stretch fight. Bold Ruler actually lost the lead with about 200 yards to go, but he came back at Gallant Man to win it by the snip of a nose.

He might have won the Kentucky Derby May 4, his next start, but Fitzsimmons and Arcaro decided that the colt should be restrained off the pacesetting Federal Hill, a horse with sharp early speed. They feared Federal Hill would drag Bold Ruler through a dizzying early pace and set it up for a stretch-running Gallant Man. Whether as a son of the temperamental Nasrullah or as a youngster whose tongue had almost been severed as a yearling, Bold Ruler clearly resented the tactic, fighting Arcaro’s exertions to restrain him. Iron Liege, Calumet’s second-string colt substituting for the injured Gen. Duke, won by a whisker over Gallant Man in one of the Derby’s most exciting renewals, with Bill Shoemaker standing up prematurely on Gallant Man, misjudging the finish and probably costing him the race.

Arcaro did not restrain Bold Ruler in the Preakness Stakes. He let him roll, and the son of Nasrullah and Miss Disco raced unchallenged through the mile and three-sixteenths, beating Iron Liege by two lengths.

Bold Ruler’s stamina—his ability to run a distance beyond a mile and a quarter—would always be suspect. The origins of this suspicion stemmed in large part from his performance in the mileand-a-half Belmont Stakes of 1957. Gallant Man’s fainthearted stablemate, Bold Nero, dragged Bold Ruler through a set of rapid early fractions, softening him up for Gallant Man’s finishing kick. Gallant Man blew past Bold Ruler at the turn for home and raced to an eight-length victory in a record-breaking 2:26^3/5 Bold Ruler, exhausted at the end, wound up third.

Bold Ruler came back later that year, gaining in stature as he went on. Like his maternal grandsire, Discovery, he began to show his gifts for lugging high weights at high speeds.

He won the Jerome Handicap by six with 130 pounds.

He won the Vosburgh by nine lengths under 130 pounds in the mud, shattering the track record that had been held by Roseben, the sprinting specialist, for fifty years. He raced the seven-eighths of a mile in a sizzling 1:21^3/5, three-fifths of a second faster than the old mark.

He won the Queens County Handicap under 133 pounds, spotting the second horse 22 pounds.

Under 136 pounds, an enormous burden for a three-year-old, he won the Ben Franklin Handicap by twelve. “Breezing all the way,” said the charts of that race.

The ending of the year was almost poetic. In the $75,000-Added Trenton Handicap at a mile and a quarter, Bold Ruler faced his two archrivals for Horse of the Year honors—Gallant Man and Round Table. The gate sprang, and Arcaro let Bold Ruler bounce, sitting as the colt opened up an eight-length lead at the end of the first three-quarters of a mile. He simply coasted for the final half mile, beating Gallant Man by two and a half. Round Table was third.

That made Bold Ruler Horse of the Year.

In 1958, as a four-year-old, even with that splinter in the tendon, he won the Toboggan Handicap under 133 pounds, spotting Clem 16 pounds, and grabbed the lead in the stretch of the Carter Handicap at seven-eighths of a mile, and won that by a length and a half under a crushing 135 pounds. He failed to spot Gallant Man 5 pounds in the Metropolitan Mile on June 14, losing by two lengths. But he won the Stymie Handicap by five lengths under 133 pounds, and that led to the nose-bobbing struggle with Clem in the Suburban, and finally to a last victory, under 134 pounds, in the mile-and-a-quarter Monmouth Handicap. He wrenched an ankle in the Brooklyn, finishing seventh with 136 pounds on his back; and then Fitzsimmons took x-rays at Saratoga, discovering the splint on the back of a cannon bone. And that ended it for Bold Ruler.

All through his campaigns on the racetrack, from his two-year-old year onward, he endeared himself to the frail old widow, Mrs. Phipps. He was always the first horse she went to in the mornings at the barn, the first horse she asked about, the horse she dwelled with the longest, the one she favored most with her time and sugar cubes. Groom Andy DeSernio used to braid a Saint Christopher’s medal into Bold Ruler’s foretop, the lock of hair between his ears, before each race. Mrs. Phipps was not a Catholic, but for Bold Ruler she overlooked nothing.

She never lost her fondness for Bold Ruler, certainly not in the dozen years since that day they sent him off to Claiborne Farm from Saratoga. Bold Ruler was led to the van waiting at the stable area. The colt hesitated a moment, balking at the sight of the van, but Sunny Jim poked him in the rump with a cane and he walked on dutifully. Inside the van, the lead shank was handed to Claiborne Farm groom Ed (Snow) Fields, and Fitzsimmons said, in parting, “Come on, Andy, we’ve done our job. It’s their horse now.” Moments later Bold Ruler was rolling southwest toward the Blue Grass.

He seemed destined for some measure of success from the outset. There was so much in his favor. Bold Ruler would begin with the choicest mares. Hancock, as well as Mrs. Phipps and her son, Ogden, and other clients at Claiborne had assembled bands of champion race and broodmares over the years—the foundations of all great studs—and to Bold Ruler many of them would be sent.

He had the pedigree himself, on both the male and the female sides, representing a popular foreign and domestic mixture of bloodlines in his ancestry: the son of a thoroughly European stallion and a completely American mare. Genetically, he was what is known as a “complete outcross,” with no name appearing more than once in the first four generations of his family tree.

Since siring Bold Ruler in 1952, Nasrullah himself had become a champion stallion in America, representing the flourishing Nearco male line, and his dam, Mumtaz Begum, was among the most prized of mares in the Aga Khan’s magnificent stud. She herself was a daughter of Blenheim II, the stallion later imported to stand at Claiborne Farm, and Europe’s “flying filly” Mumtaz Mahal. By the time Bold Ruler was sent to Claiborne, Nasrullah had already led all American sires in 1955, when his performers won 69 races and $1,433,660, and in 1956, when they won 106 races and $1,462,413. Bold Ruler was only one of several champion runners by Nasrullah: he also sired the 1955 Horse of the Year, William Woodward’s Nashua, who retired in 1956 with earnings of $1,288,565, a world record until Round Table broke it three years later. Nasrullah had also sired the 1956 two-year-old filly champion, Charlton Clay’s Leallah; the 1957 two-year-old colt champion, Nadir, eventual winner of $434,316; and Captain Harry F. Guggenheim’s Bald Eagle, America’s champion handicap horse of 1960 and the winner of $676,442.

Miss Disco, among the fastest fillies of her generation, was no doubt a source of some of Bold Ruler’s quickness, and as a daughter of one of the greatest weight carriers of all time, she gave bone and bottom to the underside of Bold Ruler’s pedigree. He had everything a sire should have.

Bold Ruler also had the brilliant speed of the Nearco tribe—speed is an important characteristic for a stud horse to have—and he had it in greater abundance than any other of Nasrullah’s sons and daughters. Moreover, he carried that speed the classic distance of a mile and a quarter, and he did it carrying high weights against horses who were just as serious about their business as he—Clem, Gallant Man, Sharpsburg, and Round Table.

Yet no one, not even a breeder as experienced and astute as Bull Hancock, could have foreseen the extent to which Bold Ruler would dominate the American sire championships. He became a phenomenon at the stud, and some believe the greatest sire in the history of American bloodstock.

For seven successive years Bold Ruler was the leading American stallion. Only Lexington, a stallion from a different era, was America’s leading sire more often, for sixteen years between 1861 and 1878. But the two horses are hardly comparable. The “Blind Hero of Woodburn,” as Lexington was known, competed with only 215 sires of runners in the last year he was the champion, 1878. In 1969, Bold Ruler was competing with 5829 sires of runners. Only three other stallions—Star Shoot, Bull Lea, and Bold Ruler’s own sire, Nasrullah—led the list as many as five times.

His reign as America’s premier blooded stallion began in 1963, when his twenty-six performers from only two crops of racing age won fifty-six races and $917,531. And this was only a foreshadowing. His influence and power as a stallion grew steadily.

In 1964—44 performers, 88 wins, and $1,457,156.

In 1965—51 performers, 90 wins, and $1,091,924.

In 1966—51 performers, 107 wins, and $2,306,523, the first time in history a stallion’s progeny ever won more than $2 million in a single season.

In 1967—63 performers, 135 wins, and $2,249,272.

In 1968—51 performers, 99 wins, and $1,988,427.

In 1969—59 performers, 90 wins, and $1,357,144.

While his two-year-olds were often precocious and brilliant, and for five years he was America’s leading sire of juveniles, Bold Ruler’s ability to transmit stamina became suspect. His sons Bold Lad, Successor, and Vitriolic, as well as his daughters Queen of the Stage and Queen Empress, were all champion two-year-olds in their divisions. Yet each failed to return as a champion three-year-old, the year the distances stretch out. No son or daughter of Bold Ruler, in all the seven seasons he dominated the sire standings, had ever won the Kentucky Derby, Preakness, or Belmont stakes.

As he added championship upon championship to his record at the stud, his value as a stallion climbed to an incalculable level. Gladys Phipps was the founder of a major racing dynasty, one supported largely by dozens of valuable broodmares at Claiborne Farm, and she and her heirs were interested in maintaining and building on it, not selling the fruits of it piecemeal.

Money could be made in many ways, but there was only one Bold Ruler, and he was the stuff to build and serve a racing dynasty. William Woodward, Sr., was fond of saying, “Upon the quality of the matron depends the success of the stud.” Bull Hancock later agreed with that, but he would add, “Remember, Mr. Woodward’s big success came when he got Sir Gallahad III as a stallion. As long as I have a Nasrullah and a Princequillo, an Ambiorix, Double Jay and Hill Prince, I’ll be on top.” (Ambiorix, another import from France, and Double Jay were leading stallions in America in the postwar resurgence of Claiborne as a thoroughbred nursery.)

Mrs. Phipps had the greatest stallion in the history of the American turf in this century, and his breeding services were not for sale. Owners of mares would have to enter into an unusual agreement with the Phippses to get a mare bred to Bold Ruler. In general, a breeder would offer the Phippses a prospective broodmare for Bold Ruler. If the mare was acceptable, she would be bred to Bold Ruler for two seasons, or until she had two foals. First choice of the foals was determined by the flip of a coin. Thus, Bold Ruler was the Phippses’ lever in acquiring foals out of some of the finest broodmares in the world, broodmares they did not own. And one of the breeders with high-class mares was Ogden Phipps’s friend, and a fellow member of the Jockey Club, Christopher T. Chenery.

Chenery had been sending mares regularly to Bold Ruler at Claiborne, where he had Hill Prince standing at the stud, since Bold Ruler stood his initial season there. The first mare Chenery sent him was Imperatrice, and in 1960 the twenty-two-year-old matron had a filly foal that Mrs. Chenery named Speedwell. The Meadow Stable’s Speedwell was Bold Ruler’s first of many stakes winners. Chenery sent his mare First Flush to Bold Ruler in 1961, and she had a filly foal named Bold Experience, who eventually won $91,477 at the races.

In 1965, Chenery ceased sending mares singly to Bold Ruler. Instead, in a coin-flip arrangement with the Phippses, he began sending two mares to Claiborne every year. The Phipps-Chenery deal, matching the greatest sire in America with some of Chenery’s choicest mares, was anything but a smash: the biggest winner, the stakes-winning Virginia Delegate who started fifty-five times and won $67,154, ended up a gelding.

Then events began unfolding in the spring of 1968 that set the stage for the most monumental coin toss in racing history, a curious flip in which the winner lost and the loser won—but neither knew it at the time.

For the breeding season of 1968, Chenery sent the mares Somethingroyal and Hasty Matelda across the Alleghenies to Claiborne Farm. Each was bred to Bold Ruler. Each conceived. Each had a foal the following year.

Hasty Matelda had a colt foal.

On March 19, 1969, Somethingroyal had a filly foal.

Just a month later at Claiborne Farm, Somethingroyal entered her heat cycle, and on April 20 she was separated from her suckling foal and taken to a stall at one end of the black creosote board breeding shed at Claiborne. In the adjoining stall, his head sticking into Somethingroyal’s stall over an open half door, was a “teasing” stallion named Charlie, a mongrel of Percheron and saddle horse ancestry. Somethingroyal was already believed to be in heat, but the breeding men wanted to be sure, so they walked her into that stall next to Charlie the teaser. Charlie nipped at Somethingroyal, sniffed at her, nuzzled her. She did not protest, backing up to Charlie, squatting, and exposing herself to him. “She was red hot,” said the keeper of the stallions, Lawrence Robinson. But Somethingroyal was not mounted by Charlie, as are some of the virgin mares. A few of the thoroughbred stallions at Claiborne come into the breeding shed screaming and whinnying. Such carryings-on can frighten a maiden mare, especially when the screamer mounts her for the first time. Docile Charlie, among his other jobs at the farm, was trotted out to mount such nervous mares—though he did not have intercourse with them—to get them used to it.

Somethingroyal was taken around the breeding shed, where the road runs past the huge sliding front doors, and walked inside the large 35-by-35-foot room. Robinson signaled Snow Fields, Bold Ruler’s groom. Fields went to the main cinder block stallion barn and unfastened the sliding bolt from Bold Ruler’s stall, with its fireproof ceiling and stained oak walls and heavy oaken door. Snow slipped a bridle on the horse, inserting a straight, stainless-steel bar bit in his mouth, clipped a lead shank to it, and walked the horse the short distance from the stall to the front of the breeding shed.

Robinson met Fields outside the shed, took the shank, and walked Bold Ruler through the door, turning him around in the nearest corner so that he faced Somethingroyal, who was standing in the center of the room with her back to him. One man held Somethingroyal. Her hind legs stood in an indentation on the gravel floor where the hind legs of hundreds of other mares had stood while breeding and bearing the weight of the stallion. Other men—including Dr. Walter Kaufman, holding a pint cup—waited nearby.

Bold Ruler’s penis dropped from its flap as he walked into the breeding shed. He was a fifteen-year-old horse who knew what he was about. The mood was sober and businesslike.

Fields immediately dipped a sponge into a bucket of warm, clear water and washed Bold Ruler’s penis, which was beginning to stiffen. Some stallions excite themselves into readiness by sniffing at a mare, but Bold Ruler was not one of them. All he needed to do was look. Robinson restrained the horse, who soon began prancing, and waited until he saw the horse was ready, watching for the penis to harden fully. Irving Embry, at the front of Somethingroyal, lifted up her left front foot, a precaution designed to prevent her from kicking Bold Ruler while he mounted her. Another man moved in and lifted the mare’s tail. Privacy was neither demanded nor afforded.

Robinson brought the horse forward and raised the shank. Bold Ruler mounted Somethingroyal in an instant. Holding the shank with his left hand, standing on the left side of the horse and mare, Robinson gave Bold Ruler one final assist: with his right hand, he guided the penis in. Bold Ruler was inside Somethingroyal no more than two and a half minutes, and Robinson watched for the single most compelling sign that the horse had covered the mare, watched for the flagging of the horse’s tail, the dipping of it during orgasm. Some stud horses dismount during copulation, either to rest or prolong the pleasure of it, but Bold Ruler rarely did. “He was one of the most wonderfullest coverin’ horses you have ever seen,” Robinson said. “The first time up, every time.”

Bold Ruler flagged. And as he dismounted Somethingroyal, Dr. Kaufman came to the horse’s side with the pint cup to catch a dripping for examination. Then Fields, with a sponge dipped into a soap and disinfectant solution, washed the horse again. Bold Ruler was then led from the barn, no more than five minutes after he walked into it, and was turned out to romp on the greenery of his nearby private pasture.

Kaufman later checked the dripping, in a routine examination, to make sure the horse had ejaculated. He had.

Two days later, on April 22, Somethingroyal was returned to the breeding shed for a second and final mating with Bold Ruler. The same procedure was repeated. There was no way of telling, Robinson said, when Somethingroyal actually got pregnant that spring. But she did.

That year, The Meadow sent Cicada to Bold Ruler as the second mare in the arrangement with Phipps, but she proved barren.

In the summer of 1969, Penny Tweedy was in Saratoga to meet Phipps and Phipps’s trainer, Eddie Neloy, in the offices of the chairman of the board of trustees of the New York Racing Association, James Cox Brady. It was time to flip the coin.

Each knew the consequences of winning the toss.

Under the rules of the flip arrangement, the winner of the flip would automatically get first choice of the first pair of foals—the two born in 1969—either the Somethingroyal filly or the Hasty Matelda colt. The loser, while getting the second choice of the first pair, automatically would get the first choice of the second pair of foals. And the winner would get the second choice of the second pair.

But there would be no second foal in the second pair. Somethingroyal was pregnant, but Cicada was barren.

So neither party wanted to win. The winner would get only one of the three foals, the first choice of the first pair. The loser of the flip would get the second choice of the first pair but also the only foal to be born in 1970—the foal that Somethingroyal was carrying on that day in August.

The coin sailed in the air. Ogden Phipps returned to his box seat and dourly told his son, Ogden Mills Phipps, “We won the toss.” And that was it. The Phippses took the filly foal from Somethingroyal. They called her The Bride; she couldn’t run a lick, finishing out of the money in four starts as a two-year-old before she was retired to the Phippses’ stud at Claiborne. The Meadow Stable got the Hasty Matelda colt, who was named Rising River because he was foaled when the river below The Meadow was flooding. He always had more problems than future.

The Bride was weaned at Claiborne in the fall of 1969 and taken from her mother at Claiborne. On November 14, Somethingroyal was loaded on a van and returned across the Alleghenies to Doswell. She was almost seven months pregnant. She spent the winter that year at The Meadow, with the other broodmares, her belly growing larger and rounder until came that chilly night of March 29, 1970, when Southworth rang Gentry from the foaling barn in the field.