At the beginning of 1988, the attention of the racing world was focused - as usual - on the road to the Kentucky Derby. At the time, if you had asked racing fans to predict the winner of the 114th run for the roses, you might have heard support for Forty Niner and Tejano, both four-time graded stakes winners in 1987; Forty Niner, the champion 2-year-old male; or perhaps Success Express, winner of the 1987 Breeders’ Cup Juvenile.
At that time, relatively few racing fans were talking about a lightly raced gray or roan filly named Winning Colors. A daughter of Caro out of All Rainbows, Winning Colors had been purchased as a yearling for $575,000, with the leading trainer D. Wayne Lukas buying her on behalf of his client Eugene Klein.
Lukas had dominated the sport through the mid-1980s, leading all trainers by money won from 1983 to 1987 while setting records in most of those years, but one major achievement still eluded him – he had not yet won the Kentucky Derby despite sending out 12 starters from 1981 through 1987.
At first glance, Winning Colors seemed like an unlikely candidate to end that streak, although it was clear from the start that she was a talented filly. After winning her first start at Saratoga by 2 ½ lengths - defeating future Breeders’ Cup Juvenile Fillies winner Epitome in the process - Winning Colors was on the sidelines for four months before winning an allowance race at Santa Anita Park on Dec. 27by 3 ½ lengths, stopping the clock in the fast time of 1:09 4/5 for six furlongs.
But while Winning Colors had yet to make her mark against top-class competition, her connections already believed that she had the talent to win the Kentucky Derby. In The Best and Worst of Thoroughbred Racing, author Steve Davidowitz wrote that after Winning Colors’ second race, “some of the grooms and stable help who worked for trainer D. Wayne Lukas made a trek to Las Vegas with one purpose in mind: to bet several hundred dollars on Winning Colors to win the 1988 Kentucky Derby at 100-1 odds.”
Her first start of 1988 yielded an easy 6 ½-length win in the one-mile La Centinela Stakes, but her next race – a narrow defeat to the talented Goodbye Halo in the Las Virgenes Stakes – did little to suggest that Winning Colors ought to take on males to see if she was of Kentucky Derby caliber. But three weeks later, Winning Colors took her talents to a whole new level in the Santa Anita Oaks, cruising to an eight-length victory while Goodbye Halo finished another 1 ¼ lengths back in third.
This performance was so spectacular that Winning Colors was entered in the 1 1/8-mile Santa Anita Derby, where she faced eight males while running her longest race to that point. With regular rider Gary Stevens in the saddle, Winning Colors took the early lead and set blazing fractions of :45 3/5 and 1:09 2/5, the latter marking the fastest six furlongs she had ever run. An ordinary horse would have tired and finished well back under such circumstances, but it quickly became apparent that Winning Colors was far from an ordinary horse. Instead of tiring, she left her rivals behind with a fantastic burst of acceleration, opening up a huge lead in the homestretch and crossing the finish line 7 ½ lengths in front.
Lukas had long known that Winning Colors was talented, but her Santa Anita Derby performance was more than he had expected. In the book Horse Racing’s Greatest Rivalries, published by Eclipse Press, it is said that Lukas “admitted he was surprised - but only ‘a little bit’ ” by Winning Colors’ stunning victory.
With the Santa Anita Derby behind her, Winning Colors was given a chance in the Kentucky Derby, where she would try to stretch her speed for another eighth of a mile while facing a top-notch field of males. Among the starters were Forty Niner, Risen Star, Brian’s Time, Seeking the Gold, and the unbeaten Private Terms – even today, the 1988 Derby field stands out as one of the best in history.
But none of that mattered to Winning Colors, who seized command of the lead right after the start and quickly opened up a large lead. With Gary Stevens riding boldly and using Winning Colors’ abundant speed as an advantage, they opened up a four-length lead down the backstretch and maintained that lead around the turn. Proper Reality was the first to challenge; he got a close as three lengths turning for home, but tired to finish fourth. Seeking the Gold tried to make a run; he ran out of steam early in the stretch and retreated to finish seventh. With just one furlong remaining, Winning Colors was in front by 3 ½ lengths and a win in the Derby seemed imminent.
But then, in the middle of the track, Forty Niner began to gain ground, cutting into Winning Colors’ lead with powerful strides. After setting a fast pace, Winning Colors was tiring, and Gary Stevens had to ask her for everything as Forty Niner drew closer. A photo finish loomed, but Winning Colors dug deep in the final strides and held on to win by a neck, becoming only the third filly in history to win the Kentucky Derby.
It was an epic victory that excited the racing world, and it would mark the pinnacle of Winning Colors’ career.
Two weeks later, an intense battle for the lead with Forty Niner in the Preakness led to Winning Colors finishing third behind Risen Star and Brian’s Time; she then finished last of six in the Belmont Stakes and was given time off before returning in the fall.
The rest did her good, and she looked like the Winning Colors of old when finishing second to the undefeated Personal Ensign in the Maskette Stakes and, after a poor effort in the Spinster Stakes at Keeneland, she returned to Churchill Downs for the Breeders’ Cup Distaff and ran one of the greatest races of her career. After opening up a 2 ½-length lead early on on a muddy track, Winning Colors looked like a certain winner turning for home, but was caught in the final stride by Personal Ensign, who retired undefeated after one of the most legendary Breeders’ Cup races of all time.
Given her win in the Kentucky Derby, Winning Colors was an easy choice as champion 3-year-old filly of 1988. She returned to the races in 1989 but achieved only limited success, winning two of her seven starts and ending her career with a ninth-place finish in the Breeders’ Cup Distaff. But while her career didn’t end on the highest note, her legacy as a Kentucky Derby-winning filly will live on forever.
Note: This story was originally published in February 2016 and has been updated.
- Winning Colors was inducted into the Racing Hall of Fame in 2000.
- Winning Colors retired with a record of eight wins, three seconds, and one third from 19 starts, with earnings of $1,526,837.
- As a broodmare, Winning Colors produced 10 foals, six of which won races, including the three-time winners Golden Colors and Danzig Colors.
- Winning Colors is one of just three fillies to have won the Kentucky Derby, the others being Regret (1915) and Genuine Risk (1980).
- Winning Colors lived to be 23 years old, passing away from colic complications in 2008.