Chip Woolley

Bennie “Chip” Woolley Jr., who will be the featured guest on the next edition of’s Talkin’ Horses podcast, scheduled for taping Tuesday, May 26, took the long road (literally and figuratively) to success in the Kentucky Derby Presented by Yum! Brands (gr. I).

Despite a broken leg sustained in a motorcycle accident, Woolley loaded up his Ford pickup truck and Turnbow trailer and drove cross-country with a little gelding named Mine That Bird to contest the Run For the Roses. Overlooked by the media during Derby week, Mine That Bird paired with Churchill Downs-based jockey Calvin Borel to post one of the most stunning upset victories in Derby history, winning by 6 ¾ lengths. The payoff of $103.20 was the second-highest in the 135 runnings of the classic.

The win, and especially the brilliant ride by Borel, generated a whirlwind of publicity for Woolley, who was a rodeo rider before migrating into training Quarter Horses in New Mexico. He has recently been transitioning into training Thoroughbreds, although there are still some Quarter Horses among his stable that totals about 25 horses.

As if winning the Derby was not exciting enough, the drama that unfolded after the race was equally riveting. Rather than ride the Derby winner in the Preakness Stakes (gr. I), jockey Borel opted for the mount on the Kentucky Oaks (gr. I) winner Rachel Alexander, a late-comer to the Triple Crown scene after a change in ownership. That resulted in Mine That Bird picking up the services of Mike Smith. Borel and the filly led throughout the Preakness before the Derby winner mounted a serious challenge in deep stretch, with Rachel Alexandra prevailing in the end.

We thank everyone for their questions; the podcast will be taped on May 26.

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