Studs and Whiskey in Lexington, Kentucky

Story and photos by Tim Leffel

In the land of Bourbon, big hats, and belles, the world’s most pampered horses enter their racing temple just two months a year. The winners will earn the real money later: as gigilos. 

Keeneland horse racing

He won the Kentucky Derby. Then he won the Belmont Stakes. Once again, the media was all a-twitter about a possible Triple Crown winner. A horse purchased for $35,000 could take it all. It would be the first in 24 years, since Affirmed won all three races in 1978. The day before the last race though, it was over by default. I’ll Have Another’s owner decided that his horse would not have another. With tendon problems, it was best to bow out now and get on to the business of earning millions.

As the winner of two major races, I’ll Have Another would likely command some very high stud fees in the future. The interested parties will be saying konichi-wa first though: a Japanese farm bought the horse last month for a cool 10 million U.S. dollars.

As I watched race after race at Keeneland in Lexington a few weeks earlier, however, the only people saying “I’ll have another” were those queuing up at the bar for a mint julep. That horse was not in the lineup for the prelim Bluegrass Stakes.

I probably wouldn’t have bet on him anyway. The way my luck was going, all my picks were crossing the finish line near the back of the pack. My only sizable win was on one horse I correctly picked to place: Putthebabiesdown. Any owner with the balls to give a horse a name like that had to be tough. He came in second.

race horse Kentucky

That bet was an anomaly. Every time I put money down on a sure thing, the favorite would lose by several lengths. I fared better the last time I visited here a few years ago, when the long shots weren’t so lucky and my daughter’s strategy of picking jockeys by their colors served her well time and again. A fried at my table was betting based on the record of the jockey. She did as badly as me. One person we overheard was just betting by name, but even to do that you’d have to be agile. Some of the top finishers would have happy names like Goodtimehadbyall, Night Party, Treasured Up, and Lord Tarzan. But then the mood would turn and the payoffs would come for Lonesome Street and June Cleaver.

I was obviously not as lucky as the founder of this legendary Keeneland race track, Jack Keene. He was a horse breeder and trainer who liked to travel internationally—not an easy thing in the early 1900s—and in 1908 he left for Japan on a trip funded by race track winnings. At a stop in San Francisco on the way, he turned an $8 bet into $10,000 in winnings. When he got to Japan, he had three horses sent over from the U.S. after seeing the sad state of the competition. In their first showing, the three won 16 races.

Gentleman Farmers (With Private 747s)
In modern times, science, breeding, and training have narrowed the gaps, to the point where gambling on even the most pedigreed horses really is a gamble. To become a winning thoroughbred horse owner now, it’s best to start out with lots and lots of money. Preferably the kind of money you make, say, running a country that produces millions of barrels of oil.

horse farm tour Kentucky

The people who own big horse farms in Lexington, Kentucky are not exactly modest farmers who started with nothing. In the old days the lands and horses were passed down by industrialists and landowners, then later bought by the likes of cosmetics tycoon Elizabeth Arden. Now the tide of globalization has washed over the Bluegrass state. The biggest farms’ owners tend to be people like the sultan of Qatar, a guy who gives all his horses’ winnings to the staff of 150 as bonuses, since this horse racing thing is really just a hobby. Then there’s the ruling family of Dubai. Sheik Mohammed bin Rashid al-Maktoum and his brother, Sheik Hamdan bin Rashid al-Maktoum, pay a fine to the FAA every time one of them flies into the Lexington airport because the private 747 planes are classified as too large for the runway. Maktoum’s Gainsborough farm has its own water purification system, its own Doppler weather monitoring equipment, and its own x-ray developing room. His horses have been experiencing a new level of pampering since he installed heated floors in the “barn.”

Juddmonte Farm’s owner is Prince Khalid Abdullah, part of the ruling family of Saudi Arabia. Castleton Lyon farm, on 1,000 acres, was owned by the late Tony Ryan, founder of Ryan Air, and is now run by his son. It turns out all those sneaky add-on fees add up to a lot, enough to fund the purchase of many rolling acres surrounded by perpetually fresh-painted wooden fences. And the pedigreed horses to graze there.

Three Chimneys Horse Farm Kentucky

Mingling With Studs

On a tour of Three Chimneys farm—one actually owned by a native Kentuckian—I got up close and personal with a few of their racehorses, now retired from racing and earning their keep with stud fees. I can’t help but notice that the stables here are nicer (and better built) than any house I’ve ever lived in. The polished hardwood ceiling and skylights are supported by heavy beams, the immaculate brick floor surrounded by walls of quarried stone. But it’s only fair I suppose: nobody pays me $150,000 a pop to screw whatever filly happens to walk through the door. And I haven’t sired 18 millionaires (in race winnings) like Dynaformer.


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