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.
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