The colt was a knucklehead, really.
He had speed and endurance in his pedigree, but if you had polled his owners and his trainer a year ago, none would have predicted that he’d gallop in the same steps as his great-grandsire, 1977 Triple Crown winner Seattle Slew.
When the gates dropped on his first race, Orb did not even break. Second race? Same thing. He did not win until the fourth and final race of his two-year-old campaign.
But where other colts might level off or become erratic, Orb seemed to get better every day.
“I’ve never seen anything like it,” said his trainer, Claude “Shug” McGaughey, who has been in the thoroughbred game more than 40 years. “His development since Jan. 1 has amazed me.”
The bay colt’s performance at a muddy Churchill Downs, where he charged from well off the pace to win decisively, has the wider sports world dreaming of a Triple Crown winner.
But for the more intimate circle of people around Orb, the victory paid off lifetimes worth of patience and devotion to the sport.
Owners Ogden “Dinny” Phipps and Stuart Janney III hail from one of the last family dynasties in American racing. They had never won a Kentucky Derby.
McGaughey, a Kentucky native, has stood among the game’s most respected trainers for decades. In six tries, he had never won the Derby.
Joel Rosario has ranked among the winningest jockeys in the country for five years. But he had never won a Triple Crown race and was a stranger to the casual sports fan.
For each of these connections, Orb created a richer legacy with his performance in Louisville. And if he can win the Preakness on Saturday, the world around him will become that much more luminous.
Family rich in history of racing
The patriarch of the Phipps family, Henry Phipps, earned his fortune in a different America, one dominated by barons of industry. The son of an English cobbler, he had the good sense to invest in a steel company with his childhood friend and neighbor, Andrew Carnegie. The Carnegie Steel Co. made both Pittsburgh boys rich beyond all imagining.
Henry Phipps' daughter-in-law, Gladys Mills, kindled the family interest in thoroughbred racing, founding a stable in 1926 and saddling her first Kentucky Derby entrant in 1928. Her son, Ogden, carried on the legacy as did his sister, Barbara, and her husband, Stuart Janney Jr.
Cousins Dinny Phipps and Stuart Janney III, who lives in Butler, are the current keepers of the flame.
“They are really the only family left that dates back to the glory days of American racing,” said NBC horse racing analyst Randy Moss.
The family's history with racing is full of tragedy and triumph, good luck and bad.
Among the great horses produced by the Phipps stable was Bold Ruler, a brilliantly fast sprinter who won the 1957 Preakness and sired a line of champions led by Secretariat.
But the family lost Secretariat, perhaps the greatest of all American thoroughbreds, in a coin flip with Penny Chenery. It was neither the first nor last piece of lousy luck for the Phippses. They also sold Seabiscuit when he was on the cusp of becoming a champion. And in 1975, Stuart and Barbara Phipps Janney watched in horror as their great filly, Ruffian, snapped her right foreleg in a race at Belmont Park. She was euthanized shortly afterward.
No matter what, however, the family held to its philosophy: Keep the bloodlines strong, hire one of the sport's most astute horsemen to be the in-house trainer, give that trainer autonomy and never, ever push the horses into races where they don't belong.
As a result of this patient, even conservative, approach, the family has allowed many Triple Crown seasons to pass without entering a horse in the sport's highest profile races.
McGaughey signed on to train the Phipps horses in 1985, and he says no Phipps or Janney has ever pushed him to be overly aggressive with a horse.
“They've been incredibly good to me over the years,” he said.
The last time the family had a 3-year-old this good was 1989 when the massive chestnut colt Easy Goer entered the Derby as a clear favorite. He struggled with a muddy track at Churchill Downs, however, losing to Sunday Silence, who again bested him at the Preakness in a scintillating neck-and-neck race. The Phipps colt finally won a commanding victory over his rival in the Belmont Stakes.
Phipps and Janney were typically self-effacing after the Derby, shifting credit to McGaughey. But the racing world responded to Orb's victory with an outpouring of love for this most traditional of operations.
“Just the fact that they've chosen to stay involved in racing for generations and have always done things the right way,” Moss said. “It's a pretty cool story.”
McGaughey shows ‘how it's supposed to be done'
It would be hard to imagine a more grandfatherly figure in the middle of a major American sports story than 62-year-old Claude “Shug” McGaughey. The 5-foot-5 trainer wears sweater vests over his small, round belly and lulls you with soft, Kentucky-accented words.
The outward picture belies the intensity of McGaughey's work and thought. He learned the game as an assistant to trainer David Whitely, a detail-obsessed workaholic. “If the screen on the stable door was the least bit out of place, he'd let you know about it,” McGaughey recalled.
When he went on his own as a trainer, McGaughey worked with multiple owners at multiple tracks and was more of a temperamental figure.
But he says, and those who know him agree, that the stability and intimacy of working with a single family was a better fit for his personality.
The Phipps stable was in the middle of a resurgence when the family hired McGaughey. And he won the Eclipse Award for outstanding trainer in 1988 for his work with Easy Goer and the other Phipps stars. He was a rising star in the sport, 38 years old at the time Easy Goer staged his great duels with Sunday Silence.
But that was the last time McGaughey brought a horse to the Preakness. And he saddled only one in the Derby between Easy Goer and Orb. The gap speaks to the vagaries of big-time breeding but also to the patience of McGaughey and the Phipps family, who were happy to develop their horses slowly and steer them to Breeders' Cup races rather than the Triple Crown.
“He didn't have the right horse, and he's not in the business of promoting himself just to promote himself,” said longtime racing writer William Nack, who profiled McGaughey in the Easy Goer days. “Shug offers a real illustration of how it's supposed to be done. A classic, classic illustration.”
Perhaps that's why so many people were so happy for McGaughey when Orb won.
“Everybody I've talked to in the racing world is thrilled, especially for Shug,” said longtime Kentucky breeder and farm executive Dan Rosenberg.
The response overwhelmed Alison McGaughey when she returned to the couple's home on Long Island after the Derby. Her dry cleaner had saved all the news clippings detailing Orb's victory. And the clerk at the liquor store handed her a free bottle of champagne.
“It's like winning the Super Bowl,” she said.
Not that any of this is likely to change anything about the way McGaughey operates. He is out of step with many of today's star trainers. You won't see him working with hundreds of horses at once or saddling five in the same Kentucky Derby, as Todd Pletcher did this year.
“That's not Shuggy,” said his wife.
“I like to keep things simple,” McGaughey added.
He's happy with his 40 or so horses and a staff that knows exactly how he wants everything done, from the preparation of a stall to the training schedule leading to a stakes race.
“It says a lot that so many of his workers have been with him 15 or 20 years,” said Jennifer Patterson, Orb's exercise rider. “Everything is so consistent. We always say that if you make it a year with Shug, you'll become a lifer.”
As the week of a big race unfolds, McGaughey is apt to grow quieter, his concentration on the work ahead deepening.
But he doesn't mind saying that this trip to Pimlico Race Course feels a little sweeter than his 1989 visit with Easy Goer. For one thing, Orb has exceeded his expectations more relentlessly than any other horse. But age has also brought perspective on how hard it is to win even one Triple Crown race.
“I always used to say that I wished I had won the Derby when I was young so I wouldn't have to worry about it,” he said. “But I don't know if that's true anymore. Having to wait 30-odd years has probably given me more appreciation of it than I would've had before.”
Rosario a smart, calm rider
It bothers Ron Anderson, the agent for the jockey who has won the world's two biggest horse races this year, that his client won't take more of the credit.
Joel Rosario defers. His instincts on the track have been compared to those of the best jockeys of all time. But as soon as the race ends, his natural preference for deflecting praise is irrepressible.
“This guy, today, it was all him,” he said while leading Orb to the winner's circle at the Kentucky Derby two weeks ago.
“He's a tremendous horse,” he said. “I let him do his thing, whatever he wanted to do.”
There is little debate, though, that Rosario is the world's hottest rider — and has, this spring, become known not for just natural talent and earned strength but the calmness and smarts to get his horse where it needs to be. Putting it that was seems to mitigate the job of a jockey. It doesn't.
“That's simply what matters most,” Orb trainer Shug McGaughey said. “Figuring out where they need to be and getting ‘em there, that's it — and it's very hard. Joel does it.”
Rosario hasn't been perfect. In Animal Kingdom's prep for Dubai, he moved early and ended up getting beaten by Point of Entry, a horse owned by Orb co-owner Dinny Phipps and trained by McGaughey.
Rosario grew up riding horses but not dreaming of doing so for a living. Like most boys in the Dominican Republic, his dream — and possible way out — was baseball. He played every day, all day, in highly regimented workouts with dozens of others. Family members — he is one of 13 kids — eventually pulled him aside and told him he was unlikely to develop the size to ever move on as a baseball player. They took him to jockey school, where he proved to be a natural. He needed only six months of training before starting his racing career at age 14.
The 28-year-old won his first race in July 2000, and was top rider in the Dominican Republic — which has one track — four times before moving to the United States in 2006.
He landed in California, eventually settling into a brash jockey colony full of big personalities who have a penchant for going fast early and hoping it works.
That, Rosario could do. His mounts earned $8 million in 2008, then $13 million the next year. He hasn't made less than $15 million since and dominated racing at Southern California's three tracks.
Last year, having never won a Triple Crown race, he headed East to ride in New York and Florida.
“I tell everyone this – and I know our sport's not exactly the bastion of truth all the time, but I mean it,” said Anderson. “Joel is the nicest kid in the world. He wants to do nothing but give credit to everyone else.”