How It All Started: The Improbable History of the Kentucky Derby

Amy Wilson tells the story:

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.

Read the whole thing.