Kentucky Derby Questions FAQs

The team - Charlie Whittingham, Bill Shoemaker and Ferdinand

Kentucky Derby Tours gets lots of questions each year about the Kentucky Derby. We thought we would share some of the questions and our answers on our blog. This is our first installment. Here goes…

Who were the oldest jockey and trainer to win the Kentucky Derby?

My pick for oldest winning jockey-trainer combination is Bill Shoemaker and Charlie Whittingham. In 1986, they teamed up to get a horse named Ferdinand to the winner’s circle. Charlie Whittingham had only had two prior runners in the Derby (Gone Fishin’ in 1958 & Devine Comedy in 1960), neither of whom placed, so he was determined to come back only if he had a viable candidate. He was 73, and his jockey Shoemaker was a mere lad of 54. When the trainer was asked why he had chosen such an old jockey, he replied “Well, he’s not so old. I’m 73!” Bill had piloted three earlier winners in 24 attempts, but it was a long drought of 21 years since his previous trip to the Derby winner’s circle.

The team looked good for making it a “repeat” at the Kentucky Derby. In 1987, Charlie returned to Kentucky with a horse named Temperance Sil. He wanted to stay at the same hotel in Louisville as he had done the year before. At the time there was an Executive West Hotel and an Executive Inn in Louisville. When we saw Charlie that week he was sure the reason Temperance Sil got a respiratory infection and never ran in the Kentucky Derby was because he had booked himself at the wrong hotel. Don’t say that trainers are not superstitious.

Who broke the two-minute mark for the mile and a quarter distance of the Kentucky Derby?

Both Secretariat and the second-place horse, Sham, broke the two-minute mark (for the Kentucky Derby as an event) in 1973. Sham was only a length and a half behind “Big Red” at the finish line. A length is roughly equivalent to a fifth of a second. This was especially remarkable in Sham’s case because he had hit his face against the starting gate and he knocked out a tooth. He was said to have bled heavily through the race, yet he was the only horse to offer any challenge to Secretariat in any of the Triple Crown series of races. In 2001, Monarchos also broke the 2 minute mark by 1/5 of a second winning the Kentucky Derby.

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