Orb's Kentucky Derby win another Phipps family success story

The most famous names in American Thoroughbred racing used to be those of dynasties possessing fabulous wealth – the Phipps family, the Vanderbilts, the Whitneys, the Wideners, and others. They owned the best stallions and mares, bred and campaigned the best racehorses. They did not merely participate in the sport; they ran it. The elites were members of the Jockey Club, the organization that ruled racing, often in a high-handed fashion.

Over the years, the aristocratic families have faded from prominence and Thoroughbred racing has become democratized. It no longer operates like a private club; anyone with enough money can play the game. But when Orb won the Kentucky Derby, giving the Phipps family its first victory ever in America’s most famous race, the colt’s success was a reminder of what the dynasties contributed to the breed.

The family’s saga began in Pittsburgh, where Henry Phipps, the son of an immigrant cobbler, grew up next door to Andrew Carnegie, the son of a weaver; they would be friends for life. When Carnegie invested $800 to buy a forge, he gave Phipps a half-interest to keep the books and manage the finances of the business that became Carnegie Steel and, later, U.S. Steel. Phipps established a rich trust for his five children. Today the Bessemer Trust manages not only the Phipps fortune but more than $60 billion for other wealthy families.

Henry’s son married the well-born Gladys Mills, who founded the Phipps racing stable in 1926. She bred and raced Bold Ruler, who won the 1957 Preakness and, after he went to stud at Kentucky’s Claiborne Farm, left an enduring stamp on the American Thoroughbred, siring 11 champions, including Secretariat. (The family would have owned the legendary Triple Crown winner but for the outcome of a famous coin flip that was depicted in the movie “Secretariat.”)

Other families’ great racing and breeding operations withered over the years – weakened either by inheritance taxes or a lack of heirs, at least ones who were interested in the sport. But the Phippses passed the torch from generation to generation. Gladys’s son Ogden became one of the country’s leading owners. Great champions such as Buckpasser and Easy Goer carried his colors – the stateliest in the sport, black silks with a cherry cap. The embodiment of patrician rectitude, he became chairman of the Jockey Club.

His son, Ogden Mills (Dinny) Phipps, who co-owns Orb with his cousin Stuart Janney III, loved the sport since childhood and, he too, succeeded to the chairmanship of the Jockey Club. His children share the passion. When Dinny was sick for a period, his daughter Daisy ran the stable. “Maybe [other families] haven’t had children with the DNA that makes them want to continue,” said Dinny. “But racing is something very important to my family.”

Continuity matters to the Phippses because its racing operation is based on long-term planning. The family believes that the thrill and the challenge of the sport is to breed horses and race the ones it breeds. It doesn’t buy youngsters at yearling sales. It doesn’t try to identify young prospects in other stables and buy them (as, say, the sheikhs of Dubai do). Nor does it run a massive operation like the sheikhs. In recent years Dinny Phipps has owned about 20 mares, plus their offspring. “They are the bedrock of our stable,” Phipps said. “We love our fillies.”

The goal is to find mares and develop female lines that will make an impact over decades. Ogden Phipps in 1970 bought an Argentine mare, Dorine, who produced a filly named Grecian Banner. She was not a notable runner, but she produced two major stakes winners, one of them Personal Ensign, the unbeaten filly champion who is enshrined in the Racing Hall of Fame. When Personal Ensign was retired, she went on to become one of the all-time great broodmares, producing four major stakes winners including the filly My Flag, who in turn foaled the 2002 champion 2-year-old filly, Storm Flag Flying, who is now part of the broodmare band. The lineage could keep producing good horses for generations to come.

In order to maintain a small, select operation, Phipps will unsentimentally cull horses and mares who are underperformers. He is undaunted by the memory of the family’s decision in 1936 to sell a small, disappointing colt named Seabiscuit, who went on to become a racing legend.

Phipps and Janney own a few mares jointly and one of them, Lady Liberty, provoked a disagreement between the cousins. Phipps wanted to sell her. “She was, in my estimation, not a great mare,” he said. “Her first two or three foals had not been much.” Janney disagreed and made a case for breeding the mare to the stallion Malibu Moon. Seth Hancock, president of Claiborne Farm, where the family’s mares reside, sided with Janney. The son of Malibu and Lady Liberty was named Orb.

Operations like the Phipps’s have become rare, not only because other racing dynasties have disappeared but also because the dynamics of the Thoroughbred industry have changed. Since the 1970s the business has been increasingly dominated by commercial breeders who sell their horses at auction, usually at yearling sales.

The sellers may be more concerned about breeding an animal with a pedigree that looks good on a catalog page than one who will be sound and durable over the long run. They prefer to breed horses who will be fast and precocious, because they know most buyers want to get a quick return on their investment. These preferences have surely contributed to the decreasing durability and stamina of modern American Thoroughbreds.

In the modern day, it’s unfashionable to breed horses who lack speed and need time to develop – horses such as Orb. The Phippses are willing to wait. Indeed, they waited since 1928 – the year of Gladys Mills Phipps’s first venture to Churchill Downs – to win the Derby.