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Winning Colors, the grey monster of a filly became the third and final Kentucky Derby winning filly to this date. Bred by Echo Valley Horse Farm’s Don and Shirley Sucher, they would send the Bold Hour mare, All Rainbows, to the stallion Caro, an Irish bred. The mating would result in a strapping grey/roan filly that they sent the to the 1986 Keeneland July Yearling Sale. While being brought out for a showing, she caught the eye of trainer D. Wayne Lukas, who said that his heart was hammering in his chest at first glimpse. Though he pretended to not be impressed, inside he knew that he would go to any price for the filly. Purchased for $575,000 on behalf of owner Eugene Klein, the grey amazon would be sent to California for her early instruction and training. The filly would be Lukas’s son Jeff’s first choice of the stable, resulting in her being sent to New York with the younger Lukas, the elder’s first assistant.  

As a result of taking their time for her large 16.3 hand frame to develop, Winning Colors made her first appearance in a race at Saratoga on August 13th, winning a 7-furlong maiden under jockey Randy Romero by 2½ lengths over the eventual Breeders’ Cup Juvenile Filly winner, Epitome. Wanting to wait on her a bit more, Lukas wouldn’t start her in the Juvenile Fillies race. Although Lukas had five other fillies in the race, he still felt that he had a better one back in his barn.  

With jockey Gary Stevens in the irons, the powerful filly would make her return on 12/27 at Santa Anita. The new combination would have a slow break; however, undeterred she would shoot to the front to take the 6-furlong contest by 3½ lengths. A month later, on January 20, Winning Colors would make her stakes debut, stretching out to a mile in the La Centinela. Her first time at two-turns, the filly would show that the added distance suited her as she won by 6½ lengths. A month later in the one mile Las Virgenes, Winning Colors would suffer her first defeat in losing the race by a neck in the final yards to the future Kentucky Oaks winner, Goodbye Halo, who also became the winner of the CCA Oaks and Mother Goose. Following the race, Lukas took the blame for the loss, saying that he didn’t do much for her training, looking past the contest.  

Pointed to the Santa Anita Oaks, an 8 ½-furlong matchup, Winning Colors would turn the tables. In leading the entire race, she would pass under the wire first by 8 lengths, with Goodbye Halo following 9¼ lengths behind. After the victory, the connections began entertaining the thought of competing in the Kentucky Derby. Gary Stevens wanted her to run in the Santa Anita Derby, while D. Wayne and Jeff felt that she could more than handle the California colts, realizing that only two fillies had won in the 50 previous running’s of the Santa Anita Derby, with only two fillies having even attempted since Silver Spoon won in 1959. Lukas, never one to shy away from taking on the boys with his fillies, was the trainer of the two fillies that started in the race, Terlingua and Life’s Magic. The timing of the race also fit Winning Colors schedule, as it was four weeks after the Santa Anita Oaks and four weeks until the Kentucky Derby. Entering his third filly in the race, she proved to be the charm. The grey spitfire would be the slight favorite for the Santa Anita Derby, with the 1 1/8-mile contest being her toughest test to date. The encounter proved to be all Winning Colors as the speedy filly took to the lead while the fastest colt in the state, Mi Preferido, tried in desperation to catch her. Unable to make a dent, the grey comet extended her lead at every quarter while setting fast fractions. Ahead by 1½ lengths through a half mile at :45 3/5, she increased to a 2½ length lead after ¾ in 1:09 2/5. As she reached the far turn of the course, it appeared for just a moment that she may be losing ground to the colts, although it was short-lived as she shot away from the field once she was asked to shake it up. She opened up to a seven length lead as she reached mid-stretch, passing under the wire a 7½ length winner, giving Lukas his 4th Santa Anita Derby victory and earning Winning Colors a date to Run for the Roses.  

Shipped to Churchill Downs to prepare for the race over the Louisville oval, Winning Colors would have three works at the track. Lukas, who had previously been tense when dealing with the press around his Derby contenders, was reserved and confident in his star filly’s chances. Usually sporting more than one runner in the big race, the conditioner kept his other stand out, Dynaformer, in the barn. The filly not only inspired confidence in her trainer, Stevens was emboldened by her and his confidence came through in his riding of the grey. The trainer and jockey had a plan for winning the race, accordingly it unfolded just as they hoped.   Not scaring any competition away, Winning Colors faced 16 other colts in the Kentucky Derby. Despite knowing that the filly would be setting the pace, no one sent their entry after her. Able to run loosely on the lead, she set an honest pace, yet not a blistering one. Pat Day aboard the East Coast hope, the 2YO Champion Forty Niner, would prove to be Winning Colors and Gary Stevens biggest threat. Hanging off of her flank while they passed the ¼ mile pole in :23, Day decided to ease his mount back rather than take her on. At the half which they slowed a bit in :46 4/5, while being trailed by Seeking The Gold who was 3 ½ lengths behind. Jeff Lukas who believed that the filly had her best shot if she could get the half in :47, was confident that she couldn’t be beat. Seeking The Gold would still be her closest competitor after 6 furlongs in an easy 1:11 2/5, though he was 4 lengths behind at that point. Falling back further, Seeking The Gold was passed by Proper Reality who trailed the leader by 3 after she ran the mile in 1:36. At the 5/16 pole, the Stevens and Lukas plan was put into effect. Having the race to herself and still full of run, Stevens let the filly open up on the field knowing that he could save what she had in reserve for the final yards. Leading by 3½ with 1/8 of a mile to go, Forty Niner started to chip away at her lead. Day, thinking that they had the race as the filly was tiring, was unaware that Stevens knew what he had left in his mount. Asking her for all that she had in the final 40 yards, she dug in as Forty Niner nearly drew even, holding off his rally with her determination, passing under the wire the Derby Champion by a neck. The winning duo covered the final half mile in :50 4/5, with 1985 winner Spend A Buck, who ran over a faster track, covering the same distance in :50 3/5, and 1976 victor Bold Forbes in :51 1/5, showing that her victory was legitimate when compared to the last two front running winners.  

Two weeks later in taking on the Preakness, she wasn’t able to get away with the same game plan as the Derby. Forty Niner was sent after the filly, hooking her into a speed duel from the onset of the race. The two competitors went back and forth, exhausting each other. Forty Niner fell back to finish 7th, while Winning Colors finished a game 3rd behind winner Risen Star. In the Belmont, the distance proved to be much for the grey filly as she crossed the line in 6th, with the victory again going to the son of Secretariat, Risen Star.  

The popular grey filly finished 2nd and 4th in her next two outings, the Maskette Handicap and Spinster. Going into the Breeders’ Cup Distaff, Winning Colors became known for her battle with Personal Ensign who had won 12 races in a row. The two would duel in an epic battle down the stretch with the grey fighting back, falling just a nose short of ending Personal Ensign’s streak. Even with the loss, Lukas would refer to it as “Everyone’s Race of the Year”. With her season complete, Winning Colors earned the 3YO Filly Championship.  

At 4, Winning Colors would only have two victories, her first start of the year in an allowance and the Breeders’ Cup Handicap at Turfway Park. During her second start in which she finished 7th, Stevens noticed the filly was making strange noises while running. Developing what is known as “roaring”, the filly underwent surgery for an entrapped epiglottis. She managed to return to the races although she never quite showed the same form that made her a champion. 

Retired, the filly that Klein rated more highly than any of his purchases except Champion Landaluce, was sent to the 1989 Keeneland November Mixed Sale. Purchased for $4.1 million by Gainesway Bloodstock Services as a broodmare, the grey superstar was the first Kentucky Derby winner to have foals that went through the auction ring. The three to sell brought $3.85 million combined. Unfortunately, her foal by Unbridled passed away, which would have been the first foal to have two Kentucky Derby winning parents. Winning Colors’ Mr. Greeley filly, Silver Colors, was bred to Honor and Serve, resulting in the 2018 Gr. I Alabama winner, Eskimo Kisses.  

The last filly to win the Derby was the first of D. Wayne Lukas’ four Kentucky Derby winners, in addition to being jockey Gary Steven first of three. The aggressive and cantankerous grey who hated to have her ears messed and would only allow 2 shoes to be put on per day managed to warm the hearts of those who were touched by her.   Passing away on February 17, 2008 due to colic, the hallowed mare was buried at Greentree Farm which is a division of Gainesway Farm.  

(Photo courtesy of KDM archives)