In late March, at Nad Al Sheba racetrack, several of the world's best Thoroughbreds battled for a share of more than $21 million in the desert heat of Dubai. The centerpiece of the weekend's racing was the Dubai World Cup—at $6 million, the world's richest horse race. The equine fete was hosted by the ruler of Dubai, Sheik Mohammed bin Rashid Al Maktoum, a man who annually splashes out tens of millions of dollars on yearling prospects, ferrying his new acquisitions around the globe on a custom-built Boeing 747. He is a man whose dreams of Dubai tilt toward artificial islands, indoor skiing, and the world's tallest building. For all his fantastic wealth and ambition, though, he has yet to saddle a winner on the first Saturday in May. With all that money, couldn't the sheik just buy the Kentucky Derby?
He's certainly been trying. Since 1999, Sheik Mohammed has started five horses in the Derby; none of them has finished better than sixth. Most have been expensive acquisitions. His most recent bid, in 2002, was with Essence of Dubai, a colt bought at a yearling sale for $2.3 million. That horse finished ninth. In 2006, the sheik shelled out $11.7 million at Keeneland for a slick-looking prospect—the second-highest price ever paid for a yearling—but to this day, the colt hasn't raced.
In 1999, at Churchill Downs, the sheik proclaimed that he would win the Kentucky Derby within four years. Those four years came and went, and what was the sheik to do? If the yearling sales weren't his ticket, perhaps the more prudent approach was to wait for a horse with demonstrated Derby promise. In 2005, he picked up Discreet Cat in a private deal for $6 million after the colt's maiden win at Saratoga, but the horse skipped the Derby over concerns about being able to go the distance. In 2006, he offered $17 million for Nobiz Like Shobiz following that colt's impressive maiden win. Nobiz Like Shobiz ran in the Derby last year, finishing 10th, but he wasn't sporting the sheik's racing silks—the offer had been rebuffed. Nine years after the sheik's first start, racing's holy grail remains out of reach. This while horses acquired at the equivalent of Crazy Eddie prices in the bloodstock market have worn the roses in May. Funny Cide, the 2003 Derby and Preakness winner, was purchased for $75,000. Monarchos, the 2001 winner, went for $170,000 at a 2-year-old training sale.
A Derby win is not only the most cherished title in horse racing. It may also be the most difficult to achieve. To be sure, it's an elusive prize: In the last 30 years, Bob and Beverly Lewis are the only owners to have won the Derby more than once.
Each year, more than 37,000 Thoroughbred foals are registered with the Jockey Club, but no more than 20 will run as 3-year-olds under Churchill Downs' twin spires. Most will have had their start in the breeding sheds of Lexington, Ky., or Ocala, Fla., and will be acquired at yearling auctions in the flash of a gavel. With no equivalent of a salary cap in horse racing, it would seem as if securing talent were simply a matter of unrivaled wealth. Yearling auctions regularly feature showdowns among the über-wealthy over horseflesh—in 2006, the sheik spent $60 million over several days at Keeneland's September yearling sale. But yearlings are immature, gangly, unproven items, and prospecting for a Derby winner among them is more than a little like trying to pick the next Asafa Powell from the members of a sixth-grade track team.
The road to the roses is fraught with more than simply long odds at predicting equine stardom. Power and strength notwithstanding, the Thoroughbred is an exquisitely fragile creature. In the run-up to May, any number of injuries may put a horse out of Derby contention. Big Brown, now the odds-on favorite after his commanding victory in the Florida Derby, was sidelined twice this year with hoof wall separations; the Derby will be only his fourth career start. The leading graded-stakes earnings winner, War Pass, will sit out the Derby—and perhaps the rest of the year—after radiographs recently turned up a fracture in his left front ankle. And with more tracks switching to synthetic surfaces, an increasing number of Derby entrants—this year, notably Californians Bob Black Jack and Colonel John—will be making their inaugural run on old-fashioned dirt in Louisville, adding more uncertainty to the equation.
The Derby's peculiarities must also be considered. While Derby prep races are traditionally run at 1 1/16 or 1 1/8 miles, most of the 3-year-old crop will not yet have stretched out at the Derby's 1 1/4 miles. Then there is the field of 20 contenders, nearly twice as many as a typical graded stakes race, where fields aren't so swollen with glory-hungry arrivistes. In such heavy traffic, horses are easily hemmed in or boxed out of a clean run. Post-position draws may also play to disadvantage, as horses breaking from far outside posts have historically fared less well at Churchill Downs. Not least, there is the spectacle that is the Derby itself—the event Hunter S. Thompson called "decadent and depraved"—the grandstand roar of 100,000 julep-wielding fans nostalgia-woozy from having just sung "My Old Kentucky Home." Swinging around the quarter pole and into the bourbon-breathed maw of that frenzied crowd would have been enough to put the fear of creator in the likes of even Thompson, to say nothing of a horse whose total career starts might be counted on one hand.
Having thus far been shut out of the money in five Kentucky Derby starts, Sheik Mohammed has changed tack and taken a page from the playbook of Calumet Farm, the legendary racing dynasty that produced Triple Crown winners Whirlaway and Citation. The breeding arm of the sheik's outfit, Darley Stud, has, like Calumet, gone to a strategy of putting battle-tested winners to use in the breeding shed. The sheik bought breeding rights to last year's Kentucky Derby winner, Street Sense, and runner-up, Hard Spun. The sheik will add those talents to his already-diverse holdings: graded stakes winners now enjoying stud careers across three continents. Thus, the empire is slowly built: Darley. Ballysheehan. Gainsborough. And most recently, Woodlands Stud, his $500 million acquisition in Australia.
While many see the sheik's investments as a shot in the arm for an ailing industry, others aren't so sure. The Washington Post's Andrew Beyer called (subscription required) the sheik's penchant for limitless spending "checkbook horsemanship." Sheik Mohammed's response: "We do not wait for things to happen, we make them happen."
This Saturday, though, there will be nothing happening for the sheik: His top 3-year-old prospects faded early and have been off the Derby trail for weeks. And so, the Kentucky Derby, in its 134th year, remains a race not easily swiped, money be damned. Those two minutes on the first Saturday in May will stay long adored because it transcends any notion of buying and selling—because it is fundamentally about the drama of achieving athletic greatness. And because, when the gates fling open at Churchill, anything can happen.