Retired Derby-Winning Jockeys Touring the Town

by Kathleen Adams

Just minutes after winning the 1954 Kentucky Derby aboard West Coast sensation Determine, Ray York gave the gray colt an appreciative kiss and wept. For the 20-year-old Massachusetts native, the victory marked a dream come true.

Fast forward 53 years, and York recalls without hesitation the confidence he felt going into the race.

“I knew I had a shot after finishing second to Hasty Road in the Derby Trial,” York said. “Hasty Road barely beat us.”

That was back when the Derby Trial was held the Tuesday before the Derby, and the 2-year-old champion managed to nose out Determine. But five days later, the results were reversed when Hasty Road simply couldn’t hold off the gray when challenged in the stretch.

It was York’s third trip to the Derby, and while he rode many more times at Churchill Downs during a seven-decades-long career, his final Derby ride occurred in 1962 aboard Sir Ribot. When York, 73, reflects on those Derbies, he pauses when asked if the experience was fun.

“No, I wouldn’t say it was fun,” York said with a laugh. “You’ve got a lot of pressure on you. It was all business the day of the Derby. The fun went right out the window.”

Many former jockeys shared similar stories with Californian Jane Dempsey, whose family started selling tour packages to the Kentucky Derby in 1947. And that’s why last year, Dempsey began inviting Kentucky Derby-winning jockeys to join the junket.

“Older, former jockeys often don’t have a lot of money to come back,” Dempsey said of the trip to Louisville. “And some of them have never seen the Derby as a spectator. They were always working on Derby day.”

Even when former jockeys did return to the historic racetrack, Dempsey said they were rarely honored. This year, Dempsey has secured two former jockeys as guests of the tour--York and Bill Boland, who in 1950 became the second apprentice jockey to win the Derby aboard Middleground.

Besides the customary trip to the backstretch, Dempsey lined up a number of other activities for the former riders to engage in. For instance, both men added their cement handprints to the “Gallop to Glory” exhibit at Louisville’s Galt House Hotel during a special ceremony May 2. And on Derby Eve, each will be recognized at the Mint Jubilee Gala.

Earlier Derby week, the pair participated in an oral history project at the Kentucky Derby Museum, which is gathering a collection of such oral histories for research purposes, said Joyce Trammell coordinator of the project. There is no time limit on how long someone like York or Boland may speak.

“We finish, when we finish,” Trammell said. “But they usually run about an hour.”

York’s recording session was no exception. “I asked him how it felt to step out onto the racetrack to the sound of ‘My Old Kentucky Home,’ and he teared up, and I teared up, and we had to stop recording for awhile,” Trammell said.

York said just being back in Louisville during Derby week has brought back a flood of memories. But the thing he looks forward to the most is being back at Churchill Downs on Derby day.