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Horses wound and horses heal. A young man once let his father call a coin toss, and from that simple act the greatest racehorse in history ran in someone else's silks. Another young man once watched a great filly mortally injured right in front of him—and in front of America—a very famous filly owned by his parents. And a young trainer with bluegrass in his veins lost a Kentucky Derby that he thought he could have won, and for more than two decades wondered if he would ever get the chance to make it right. They threw their passion into the game, as horsemen do, and only the game could fully give back what the game had taken away. Their time would come when the horse was right.
So the three of them gathered in Louisville last Saturday as a cold rain fell on Churchill Downs, drenching the crowd of 151,616 that had come for the 139th Kentucky Derby. It was a day when fans sought cover beneath overhangs, hid their day's outfits beneath garbage bags and ponchos and huddled against a stiff wind and 55º temperatures. The track was turned to soup. Late in the afternoon Ogden Mills (Dinny) Phipps, 72, and his first cousin Stuart Janney III, 64, sat in box seats with their families.
It was from there that they watched as a powerful 3-year-old bay colt named Orb, owned by the two of them and trained by Claude R. (Shug) McGaughey, splashed beneath the twin spires at the end of a breathtaking three-furlong drive under dynamic jockey Joel Rosario to win the Derby by a dominant 2½ lengths as the 6--1 cofavorite. The taciturn Phipps, a stout man with a round face and a perpetual squint, turned to his kids at the finish and said, deadpan, "Well, that was all right."
McGaughey, who has trained for Phipps and Janney for 25 years, would betray much more an hour later when he said, "I think there's more there; I don't think we've bottomed out." Orb, named in reference to his sire, Malibu Moon, has won five consecutive races, including all four of his starts this year. He did not just win the Derby, but in running three-to-six paths wide for the entire 1¼ miles, he also proved himself decisively the best in the field of 19 horses and a genuine threat to win the May 18 Preakness Stakes at Pimlico in Baltimore and chase the Triple Crown. For the three principals, it was a cleansing moment deep into their long and distinguished racing lives, each of which had been marked by a significant and infamous trough.
In August 1969 Dinny Phipps was a 28-year-old Yale graduate and financier who had also dived into the family business of thoroughbred racing and breeding, which had been established in 1926 by his and Janney's grandmother, Gladys Mills Phipps. Through an unusual arrangement between the Phipps family and the owners of Virginia's Meadow Stable, the Phippses had agreed to divvy up the offspring of its stallion Bold Ruler with a coin flip. Dinny held that season's breeding rights to Bold Ruler but was away on business. His father, Ogden (who died in 2002), won the coin flip with Penny Tweedy, the daughter of Meadow Stable's Christopher Chenery, who wanted to fulfill her late father's dream of winning the Derby. Ogden's choice resulted in a filly his family named The Bride. Tweedy was left with a colt who became Secretariat.
Six years later Stuart Janney III was a 26-year-old law school graduate working as a legislative aide to U.S. senator Charles Mathias of Maryland. On July 5, 1975, Janney drove north to Belmont Park racetrack to watch his parents' unbeaten filly Ruffian run a nationally televised match race the next day against Kentucky Derby winner Foolish Pleasure.
Less than a half mile into the race, Ruffian took a narrow lead and then broke down horrifically, sesamoid bones shattered in her right foreleg. Janney went to Ruffian's barn and saw the damaged filly with her head on trainer Frank Whiteley's shoulder. He heard the next morning from his father that she had been euthanized. "I remember being so crushed," says Janney. The family spent much of the rest of that summer at their house in Maine answering Ruffian's fan mail, which Janney says filled a bedroom, in stacks two feet high.
Fourteen years later, on the first Saturday in May 1989, Shug McGaughey was a 38-year-old trainer, a native of Lexington who had handled unbeaten filly Personal Ensign for Phipps's father the previous year and now brought his long-striding colt Easy Goer to the Kentucky Derby. It was so cold that day that sleet pelted the Downs and Easy Goer was beaten by Sunday Silence. McGaughey has never watched a video of the full race, though he drew some solace from Easy Goer's eight-length victory in the Belmont five weeks later, which denied Sunday Silence the Triple Crown. McGaughey returned to the Derby just once in the ensuing 23 years, to finish 10th with a big, dull colt named Saarland in 2002, refusing to force a lesser horse into the race.
Janney and Phipps have long since emerged from their setbacks in the 1970s to achieve success together as owners and breeders. "There are highs and lows," said Janney after the Derby. "[Ruffian] was a big low, way down, but if you can't take the lows...." They have won important races but never the most important race. McGaughey, 62, was inducted into the National Museum of Racing's Hall of Fame in 2004, but never let go of the Derby. "I don't really know that I need it to punctuate my career," McGaughey said four days before the race. "But I need it [for] myself." Two hours after Orb's victory, he stood beneath dim lights at a party in the Derby museum and said, in his thick drawl, "My life is pretty good right now."
The long trip to that moment began when Janney's father, Stuart Janney Jr., was killed in a one-car auto accident in 1988, at 81. Stuart III was absorbed in a financial career then and was disinclined to take up his father's stable. His uncle, Ogden Phipps, Dinny's father, made a strong case for him to stay in the sport, offering, "I'll be your partner on some of these horses."