The issue has never been a lack of quality. Because if there is one thing all parties involved won't ever be questioned about, it is their ability to repeatedly cultivate once-in-a-lifetime Thoroughbred talent.
In the 28 years since the Phipps family handed Shug McGaughey the job of conditioning the products of its heralded breeding program, the Hall of Fame trainer has developed a procession of top-level horses to carry the operation's famed black silks — from the immortally flawless Personal Ensign to four-time Grade I winner Point of Entry, who currently graces the shedrow.
McGaughey is just as intrinsically linked to the exploits of runners owned by Stuart Janney III, a pairing that blossomed when the late Odgen Phipps paved the way for his nephew to have horses with his new private trainer.
To point out gaps in their trophy cases would almost qualify as nitpicking, an audacious critique of a grouping that has given Thoroughbred racing some of its all-time greats.
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Fact is the most celebrated race in the sport has somehow remained missing from one of the industry's most distinguished partnerships, though that goal has never been the driving catalyst of their programs.
"The Kentucky Derby would be special to us, absolutely special," said Ogden Mills "Dinny" Phipps, owner of the Phipps Stable his late father founded. "It is lacking from the résumé, if you want to put it that way."
Regardless the outcome of the first leg of the Triple Crown May 4, the sun will set that evening with the reputations of McGaughey and first cousins Phipps and Janney intact. But if their latest representative continues to build upon his progression, all three may be able to rest their heads that night without the weight of a certain albatross.
Fate aside, McGaughey will have a Kentucky Derby starter for just the seventh time in his 37-year career, a bay colt named Orb bred and owned by Janney and Phipps Stable.
Eleven years have passed since McGaughey last found himself in the Derby crush, saddling the Phipps' Saarland to a 10th-place finish in the 2002 edition of the classic. When the Lexington native led Saarland over that day, it marked McGaughey's first appearance on the Derby scene since Ogden Phipps' champion Easy Goer finished second to eventual Horse of the Year Sunday Silence in the 1989 renewal of the 11/4-mile classic.
A Kentucky Derby win is the gold standard for horsemen, yet it has become a target that McGaughey and his owners only seek if a prospect emphatically carries them to the firing line.
When Orb captured the Grade II Fountain of Youth Stakes over Grade I winner Violence on Feb. 23, the 62-year-old McGaughey could sense an impending tug toward Louisville. When the son of Malibu Moon toppled one of the best fields of 3-year-olds this year in the Grade I Florida Derby March 30, McGaughey's warm but collected demeanor let some trickles of excitement surface.
"Some people ... that's their key component is to get to the Kentucky Derby and Triple Crown races," McGaughey said. "We start out with 20-25 2-year-olds and if there are 5-6 of them I think could be OK, I've got to try and make them last. So I would love to be competitive in the 2-year-old races and the Breeders' Cup, and I've won some, but it just hasn't been the way it's worked in the last few years.
"Our motto as I've said is that I'm not going to run in any race just to be running — especially in races that are as tough as the Kentucky Derby — unless we think we've got the horse that can possibly give us the opportunity to win. I think as of today, we're taking the right horse over there."
As McGaughey made the drive to Payson Park Training Center the morning after Orb's Florida Derby triumph, he had ample time to contemplate what a Kentucky Derby win would mean at this stage of his career.
Twenty-four years ago, the last thing anyone expected was for McGaughey and the Phippses to go one more year — let alone decades — without having that achievement on their mantle.
An occasional visitor
According to the buildup for the 1989 Kentucky Derby, there wasn't a race being run so much as a crowning in progress.
Though Easy Goer had suffered a stunning defeat over the Churchill Downs strip in the Breeders' Cup Juvenile the previous November, the juvenile champion had slayed his challengers in his three Derby prep races, winning the Gotham by 13 lengths in near world-record time and taking the Wood Memorial by 3 lengths.
"At that time with Easy Goer, maybe I thought it was a given," McGaughey recalled.
Sent off as the overwhelming Derby favorite, Easy Goer ran into a fellow future Hall of Famer and nemesis in Sunday Silence, who would go on to defeat his rival in their epic Preakness Stakes rematch before Easy Goer ruined Triple Crown hopes with his 8-length victory in the Belmont Stakes.
At that point, McGaughey — who was named the private trainer for the Phippses at the end of 1985 — had started five horses in the Derby over a six-year span including 1989 third-place finisher Awe Inspiring.
Shocked as he was to see the horse who couldn't lose not finish first beneath the Twin Spires, McGaughey sure didn't fathom he'd become only an occasional visitor.
"I did think (I'd have regular Derby starters) because I'd been there with five horses so, I thought we would be a lot more competitive in Triple Crown races than we have been," McGaughey said. "I don't think I've made any mistakes along the way, and I have looked back at it. But rightfully I'm disappointed that I haven't been more competitive in the Triple Crown."
Even in defeat, Easy Goer set the bar for McGaughey of what a horse capable of winning the 10-furlong test needs to have in terms of physical and mental advancement.
In 1998, McGaughey saddled Janney's Coronado's Quest to victory in the Wood Memorial but bypassed the Kentucky Derby as they felt the colt's erratic temperament would be ripe for a meltdown.
"I think I kind of understand more now what it takes, that you have to keep everything in perspective than I would have back then," McGaughey said. "Back then if I had won it, it would have been 'Well, when am I going to win it again?'. Right now I'm just thrilled to have the opportunity to have the chance to be able to try and win it."
Thanks to the enduring strength of some wonderfully cultivated equine families, McGaughey has taken comfort in knowing the opportunity to have great horses will likely be a constant.
The Phipps broodmare band, renowned as they are for their on-track champions, is as elite as they come with generations of top runners tracing their talent back to female lines that pre-date McGaughey himself.
"Our fillies are very special to us and we have tried to breed them to good things and nurture them along," said Dinny Phipps. "This family (Orb's) is not quite as live as it could have been for a couple of generations but it's been a heck of a family and it goes back into the '40s and '50s."
Orb indeed is a classic representation as he comes from the same female family as the legendary Ruffian, who was campaigned by Janney's parents. His rise to the ranks of leading Kentucky Derby threat is also one that necessitated McGaughey's patience because it all came together in a sudden spurt.
Before his gallop Saturday morning at Churchill Downs,
Orb stood alert and kindly, but the bay colt displayed some terrible gate habits in his early juvenile starts before breaking his maiden fourth time out at Aqueduct last November.
When McGaughey brought the colt to Florida for the winter, he figured he might get a couple allowance races into him at Gulfstream Park with the expectation his late-running charge might struggle over the speed-favoring track.
Instead, Orb continued to stun his trainer with his rapid development, winning three races over the Gulfstream surface. Orb not only rallied off quick fractions in the Fountain of Youth, he also showcased tactical ability not pace dependent when he sat closer up in the Florida Derby before overtaking Itsmyluckyday.
"This horse has improved so much from the first of January to the first of April, it's almost mind boggling to me," McGaughey said. "Two, three months ago, I would have never thought I would be sitting here talking about (the Derby) with him. He just kept going in the right direction."
Given their collective commitment to only go where their charges dictate, Orb's connections can't argue with his hard sell — and the hardware that may result.
"We think 3-year olds still need time to develop and if you don't have the right horse, you shouldn't be running (in the Derby)," Phipps said. "We want to run the right horse in the Derby, one that is right for the race. That is what we think we have in this horse."
McGaughey's Derby starters
1984: Pine Circle (6th) and Vanlandingham (16th)
1988: Seeking the Gold (7th)
1989: Easy Goer (2nd) and Awe Inspiring (3rd)
2002: Saarland (10th)