When you think of the Kentucky Derby, you picture a field of twenty, mighty colts storming over the track of Churchill Downs. You think of one colt rising above all others to claim the roses and crown himself as a top stallion for the future. But sometimes, it takes more than a colt to achieve the coveted prize that awaits at the end. Sometimes, it takes a filly to get the job done. Throughout the history of this legendary race, three fearless fillies have stepped up to the plate and taken down the boys, forever leaving their mark in the sport as the only females to take the roses.
When Harry Payne Whitney bred his prized mare, Jersey Lightning, to champion sire, Broomstick, he had high hopes for the colt that the breeding would produce. He believed that the blood of Jersey Lightning and Broomstick would produce a champion colt, swift enough and strong enough to win at the highest level. But when Whitney found a filly staring back at him after the mare’s delivery, the hope that he had poured into this mating quickly turned to bitter regret. This was not the result that Whitney had planned for, so when it came time to name the blazed filly, he let his emotions, and a bit of impulsiveness, do the talking. He named the filly after the only thing he was feeling at the time: Regret.
Colt or not, Regret was a force to be reckoned with in her own right. As a two-year-old she ran all of her male counterparts off their feet, scoring in the Saratoga Special, the Sanford Stakes, and the Hopeful Stakes, three of Saratoga’s major races for young horses. It was a feat that has only ever been matched by three other horses, such as, Campfire, Dehere, and City Zip. Regret’s obvious speed and heart quickly put her in a class of her own, reminding her owner that a champion is a champion, regardless of gender.
When the 1915 Kentucky Derby began drawing near, Whitney knew that his vivacious filly belonged. The Kentucky Derby is a race that brings together the best competition there is, and as Regret demonstrated as a two-year-old, she certainly had what it took to be the best. Despite any discouragement that Whitney experienced when the filly was born, he now knew that it was quite possible for a filly to hold her own against even the strongest of males. There was no reason to keep her out of the race for the mere reason that she wasn’t a colt.
The only thing that was going against Regret was the simple fact that she had not had a previous race that year leading up to the Kentucky Derby. After such a long layoff from the races, there was question to whether or not she would be fit enough to handle the rage and distance of the race. Entering a horse in any major race without having a single prep would be considered ludicrous nowadays. But Whitney knew what his young filly was capable of. The visions he had when he first brought together Jersey Lightning and Broomstick were starting to become reality.
On the eve of the Kentucky Derby, British ocean liner, Lusitania, sank off of the coast of Ireland after being fatally struck by the torpedo of a German submarine. Among the 1,200 souls lost that tragic day was Alfred Gwynne Vanderbilt, the brother-in-law of Harry Whitney. Vanderbilt lost his life after selflessly taking his own life jacket off of himself to give to a woman that he didn’t even know.
After the discovery of the Lusitania’s demise, rumors began to circulate that Whitney would scratch Regret out of the race to pay honor to his brother-in-law’s untimely, yet heroic end. However, the whispers remained as nothing but rumors, and Whitney remained steadfast in his decision to run his filly in the grand Kentucky Derby.
The largest field in Kentucky Derby history for that time assembled under the Twin Spires for the 1915 “Run for the Roses”. Sixteen stately thoroughbreds lined up to do battle. History was against Regret in that moment, as every filly who had previously competed in the Derby before had failed. But history was meant to be changed, and if any horse could pull it off, it was Regret.
Regret fiercely charged toward the head of the field the moment the race began. With swift, confident strides the filly effortlessly propelled herself into a commanding position, flaunting her speed and never looking back. She was going to show the colts what she was made of. If they wanted the glory, they would have to come and take it from her. Based on the way that Regret taunted her male rivals on the front end, it appeared that she knew full well that they couldn’t stop her.
Clouds of dirt flew wildly up from Regret’s pounding hooves as she led the stampede into the stretch. With a massive wall of hotheaded colts chasing after her, Regret made a beeline for the wire, ready to finish them off. Try as they might, none of the colts could get close enough to threaten. With a powerful kick of her legs, Regret glided over the wire, putting her male rivals to shame by two crushing lengths. By crossing the finish line first, Regret became the very first filly to ever take home the roses, and the first horse of either gender to win the Kentucky Derby with a current, unbeaten record. The champion horse that Whitney had always dreamed of was here, and she was very real. She just came in a form that he hadn’t expected.
Euphoria exploded throughout the winner’s circle when Regret entered to be adorned in her roses. History had been made and the young filly’s name was sure to be on headlines everywhere. Regret was living proof that yes, a girl can run with the boys and win. As the photographers and press swarmed in, a jubilant and victorious Whitney remarked, “You know, this is the greatest race in America at present time, and I don’t care if she never starts again. The glory of winning this event is big enough, and Regret can retire to the New Jersey farm anytime now. I told Rowe (her trainer) I didn’t care if she never won another race if she could only land this one. I have seen much bigger crowds than this one in the East and abroad, but I never saw a more enthusiastic one.”
The remarkable story of Regret’s dauntless rise to victory brought major publicity to the Kentucky Derby. As Matt Winn described, “The race only needed a victory by Regret to create some coast-to-coast publicity to really put it over. She did not fail us. The Derby thus was made an American institution.”
Sixty-five long years passed before a filly came along that was able to duplicate Regret's heroic feat against the males in the Kentucky Derby. The heroine came in the form of a glistening, red filly with a blaze of ivory splashed down her face. Her name was Genuine Risk, and as history would tell, she was a filly who would live up to her name.
Genuine Risk came into the 1980 Kentucky Derby with an attractive record of six wins from seven starts. Her lone blemish came in her start before the Kentucky Derby, when she took on the boys in the Wood Memorial. She ran third that day in her first defeat, but the loss wasn't enough to discourage her connections. The filly had as much class and grit as any colt, and belonged in the "Run for the Roses". Her team knew that she could hold her own against her larger, male rivals, even if they did hand her defeat in the Wood Memorial. It was simply one battle that the boys had won over her, not the war. The ultimate prize awaited in Louisville, and there Genuine Risk would have her vengeance.
The starting gates shattered open to the roar of the crowd and the highest ranked three-year-olds in the country took flight. Genuine Risk settled in nicely behind the leaders and never let them out of her sight. The filly was on a mission, and she was not about to let anyone stand in her way. As the stampede raged over the track, Genuine Risk waited for her moment to strike.
The final bend loomed ahead, taunting the approaching field. In the stretch, the race would be won or lost. There was no time to lose. Each rally had to count. It was now or never, and Genuine Risk seized the moment. The intrepid filly extended her efficient stride and took off like a rocket. She began powerfully flashing past horses, flaunting her speed and strength with every leap. The males wildly gave chase, but were only left with a view of a red tail as Genuine Risk sprinted into the stretch.
The crowd pulsated with excitement at the sight of a filly leading the way in the Kentucky Derby. History was on the line before their very eyes. The applause from fans roared from the infield all the way to the grandstand, shaking the ground like thunder. Fueled by the frenzy of the crowd, Genuine Risk unleashed a scintillating burst of speed in the stretch, separating herself from her foes and shutting down their attacks.
Rumbo and Jaklin Klugman ran their hearts out in the stretch, desperately chasing after the run away filly. They threw every punch they could, but Genuine Risk simply spit in their eyes and punched back harder. She was an unstoppable force as she flew down the stretch, the roses now in her sights. A feeling of amazement and awe descended over Churchill Downs as Genuine Risk blazed toward the wire. A filly was going to win the Kentucky Derby and add her name to history. As the striking realization hit, track announcer, Dave Johnson bellowed out "It's Genuine Risk and she's genuine! Genuine Risk is going to win it!!". There was no mistaking the admiration and excitement in Johnson's voice as he declared the filly the winner. Genuine Risk scorched over the wire by a solid length, forever engraving her name into history as only the second filly to claim the roses.
It didn't take long for another filly to follow in the footsteps of Regret and Genuine Risk. In 1988, an big, imposing filly by the name of Winning Colors entered the Kentucky Derby. It was a particularly strong group of runners that lined up for the Kentucky Derby that year. Top names such as, Risen Star, Forty Niner, Seeking the Gold, Private Terms, and Brian's Time headlined the race. Not many people knew it at the time, but it would be the lone filly in the race who would be the true force to be reckoned with. As stellar as the colts were that year, it was going to be the filly who would get the job done.
The Kentucky Derby was not Winning Colors' first rodeo against the boys. In her final prep before the Kentucky Derby, the intrepid filly beat up the boys in the Santa Anita Derby. With seemingly endless energy, the silver beast led the field gate to wire, opening up with a breathtaking acceleration in the stretch that carried her to glory by almost eight lengths. Those who surrounded the magnificent filly knew that she would show no mercy in Louisville, and thus the bold decision was made for Winning Colors to continue competing with the boys.
The instant the starting gates opened in the Kentucky Derby, Winning Colors made her move that would result in her winning the race. Without hesitation she sprung to the front, brazenly taking the lead and refusing to look back. The spirited filly wouldn't stop for anything as she blazed over the ground. With furious strikes from her hooves, Winning Colors bolted through solid fractions, ruthlessly daring her male rivals to keep up. The filly never faltered as she stormed the track of Churchill Downs, fully prepared to take her rivals all the way around.
With unwavering confidence and endless speed, Winning Colors opened up on her challengers. She flaunted her strength all the way down the backstretch, refusing to relinquish her commanding position. The filly was determined to finish what she started, and she was not about to let anyone stand in her way.
The crowd at Churchill Downs erupted into an ocean of cries and applause when Winning Colors swung into the stretch and bolted for the wire, full steam ahead. A massive mob of hot-headed colts chased behind her, trying to close the gap with everything they had. However, their herculean efforts would not be enough. Winning Colors was right where she was when the race began. She was still in front and going strong, making each and every stride a winning one. As the wire came, Forty Niner made a powerful bid for the lead, but was left wanting. Winning Colors did not make it this far only to be passed in the end. With a determined thrust of her head, Winning Colors dashed over the finish line, declaring victory by a neck. The roses belonged to Winning Colors, and thus, she took her place in history as only the third filly to ever wear the cape of red flowers.
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