35 years later, remembering Winning Colors as the last filly to win the Derby

Winning Colors remains one of just three fillies ever to win the Kentucky Derby.
Published: May. 4, 2023 at 2:35 PM EDT
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LOUISVILLE, Ky. (WAVE) - While Secretariat’s 50th anniversary is celebrated at Churchill Downs and beyond, another important anniversary is noted: the last time a filly has won the Run for the Roses.

Winning Colors’ 1988 win is still remembered by fans worldwide, not least of all by her trainer, D. Wayne Lukas. He hadn’t won a Kentucky Derby before her.

“He’ll tell you that’s probably one of his favorite Derby winners because that was definitely his first one,” Sean Collins, assistant tour manager at the Kentucky Derby Museum said. “It kind of became a running joke that he would never win the Kentucky Derby because all the time he would run three, four horses in the race, and none of them would end up winning.”

Until Winning Colors came along; Lukas was so confident in her potential that she was the only horse he ran in the 1988 Derby.

“[Lukas] says as soon as he saw her out there in the sales ring, his heart just started pounding,” Collins said.

Lukas might have noticed her size first.

“She was massive,” Collins said. “She was nicknamed ‘the Amazon’ because of how big she was.”

But, that wasn’t her only attribute. Collins said Winning Colors had a fighting spirit, too.

“When she was here for the Derby leading up to the race itself, getting saddled in the Paddock, she actually was kind of lunging at all the male horses trying to bite at them, trying to intimidate them a little bit, so that way they wouldn’t want to pass her when they saw her out there on the racetrack,” Collins said. “They were too afraid of her at that point.”

One horse, Forty-Niner, did try to get close, however, and right at the finish.

Collins describes what happened next: “Gary Stevens [Winning Colors’ jockey] just gives her a little bit more of a chirp, lets her out a little bit more. She just digs in; she wins the race by a head. [Stevens] knew that he had it in the bag the whole time, and poor Pat Day [Forty-Niner’s jockey] found out a little bit too late that he wasn’t going to get by Winning Colors.”

Winning Colors remains one of just three fillies to ever win the Kentucky Derby. Thirty-five years later, she remains the last, too. Fewer and fewer fillies are entered because most are run in the Kentucky Oaks, a fillies-only race, the day before the Derby.

“It’s a great reminder that the girls can hold their own against the boys when they run against them, and that they’re just as competitive and just as good as the boys,” Collins said. “When you have that star filly, they should come take a shot at the roses.”