Starting with jockey named Winn, Kentucky Derby couldn't lose

It started out lucky, then it stumbled and had no chance. Then, out of the blue, a regional horse race in May, run with ordinary horses and staged a really long way from the big-money stables, suddenly became the most important horse race in America.

How do you explain that?

And while we're at it, how did that race become even bigger than a horse race? How did it get to be an event that is not just a horse race but a spring rite, an American holiday and a party excuse?

Was it money? Luck? Geography? Hype? A confluence of stupid choices by some men and smart ones by others? Was it destiny?

A heap of yesses and a maybe.

Mostly, though, it was a man with the improbably promising name of Winn, who rode in on a horse named Regret.

In the beginning

The first time it was run, the Kentucky Derby wasn't even the main event at the track that day. But if beginner's luck means anything, it had that.

On May 17 in 1875, a Monday afternoon, Kentucky Derby winner Aristides ran the then-11/2-mile race in 2:373/4, a world-record time for a 3-year-old. The New York Sun noted the next day that Louisville's inaugural event was "extraordinarily successful." Of course, it didn't turn a profit for 29 years, and that feat was accomplished by a man who was in the infield on that first Derby day, standing in the seat of his father's grocery truck so he could see: 14-year-old Martin Joseph Winn.

For the first quarter-century of the Derby, Churchill Downs was run by Col. Lewis Clark, who built the track to face the afternoon sun; who thought sportswriters shouldn't bet on races; and who, in 1886, banned bookmakers, which so angered owners such as James Ben Ali Haggin, owner of the great Ben Ali, that they took to boycotting the track.

These were not Derby builders. In 1902, desperate to keep the track alive, a group of investors approached Winn, now called Matt, to buy in. Winn set about offering his friends good seats to the 1903 Derby, then offered them memberships at $200 apiece to an exclusive clubhouse at the Downs. He simultaneously placed ads in the New York papers extolling the Kentucky Derby as the greatest race ever run.

"What he had that no one before him did," says Andrew Plattner, author of The Kentucky Derby Vault: A History of the Run for the Roses, "was, he really understood what the Derby could be."

Winn was a dreamer, but he also was pragmatic. He promptly turned the grandstands around. He became a partner with the Empire City Race Track in Yonkers, outside of New York City. It was his calculated move to get closer to the Eastern racing establishment, and it helped him become close with all the New York sportswriters. When May rolled around, he paid all the sportswriters' expenses to Louisville so they feel the river breeze and drink the commonwealth's bourbon.

The sportswriters, duly impressed, drunk or paid well, did their part.

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