Leading up to the 1988 Santa Anita Oaks, the filly known as Winning Colors had proven to be virtually unstoppable. Returning from a layoff after breaking her maiden at Saratoga the previous August, the daughter of Caro made her presence felt in Arcadia. First came a win against allowance company and then a victory in the La Centinela by a combined ten lengths. She narrowly missed making it four straight in the Grade I Las Virgenes, but still came in second.

The winner in that race was Goodbye Halo, and the two ladies would meet again in the Santa Anita Oaks a few weeks later. It could be said about Winning Colors that she loved to run, and she loved to lead. Those who followed her before the Oaks likely had little to no doubt that the filly would control the pace in the Oaks.

Only two other horses, Jeanne Jones and Pattern Step, joined the lineup. At the break, Winning Colors broke from the rail position while Goodbye Halo moved up from the extreme outside of the group. Winning Colors did not relent, setting the early pace from the inside. She moved effortlessly, leading her opponents while looking quite relaxed. Jeanne Jones and Goodbye Halo tried to make a race of it in the backstretch, but Winning Colors came to race.

Jeanne Jones drew level around the far turn, but the leader surged forward as if no one was there. Winning Colors was going for victory, and jockey Gary Stevens had sat still on her to that point. Widening her lead as she turned and straightened for the stretch run, Winning Colors effectively ended the Oaks for 1988. No one had an answer for her in the stretch, and the roan filly avanged her loss to Goodbye Halo while notching her first Grade I triumph.

Winning Colors was being pointed to the Kentucky Oaks after the win, along with the Kentucky Derby. A filly winning the latter was extremely rare, with just Regret and Genuine Risk the only two females to be on the list of champions. There was another race being considered for Winning Colors in the interim, too. That was the Santa Anita Derby.

D.Wayne Lukas, the trainer of Winning Colors, was no stranger to sending fillies to take on the boys, and that had resulted in wins. A notable example was Althea, who captured both the Grade II Del Mar Debutante and Del Mar Futurity in a ten day span back in 1983. Like Althea in the Futurity, it looked like Winning Colors was being considered for a showdown with the boys. The question was where.

The answer was the Santa Anita Derby, the final major Kentucky Derby prep race in California. As with the Run for the Roses, not very many fillies had won the race since its inception in 1935. Only Ciencia (1939) and Silver Spoon (1959) had conquered it, so Winning Colors was taking on history in addition to eight rivals.

The betting public liked her chances, making the Santa Anita Oaks champion the favorite. At the start of the race, Winning Colors employed the strategy used in the Oaks, staring squarely at the front and moving to the lead on the inside. Mi Preferido and Tejano (a stablemate of Winning Colors) went to her outside and briefly battled in the opening seconds, but the filly charged forward and guided the field around the clubhouse turn.

Watching the field go down the backstretch, the fans at Santa Anita saw the gold silks with the blue lightning bolt of owner Eugene V. Klein (who at one time owned the NFL's San Diego Chargers), worn by Stevens as he and Winning Colors maintained first place. No one was mounting a bid as the two went into the far turn, and the lead gradually increased. Winning Colors, perhaps with a sense of flair or maybe knowing that she was in a big race, left the field fighting for the minor awards. There was a competitive spirit, and it was on display in the stretch. Nothing but victory was going to be achieved.

There were cheers in the grandstand as the fans witnessed history unfold before them. The 1988 Santa Anita Derby was becoming an instant classic. Winning Colors got to the line 7 1/2 lengths ahead of Lively One in a final time of 1:47 4/5. Klein was confident about the near future after the race, stating that his filly would win the Kentucky Derby.

He proved to be right. Four weeks later, Winning Colors, as was her want, made the lead and stayed there at Churchill Downs, becoming just the third filly to win the first leg of the Triple Crown, ensuring her place in Thoroughbred racing history.

Winning Colors is remembered for her stirring win that First Saturday in May, and understandably so. However, she made a place for herself in Santa Anita lore earlier that spring. Only one filly by the name of Silver Spoon had ever won both the Santa Anita Oaks and Santa Anita Derby before Winning Colors. But Winning Colors captured both of those races and the Kentucky Derby. No filly has done that since.

During the winter and spring of 1988, the racing world saw a special horse put on a display of greatness. Winning Colors was aptly named, for winning was something she knew how to do.

Sources: Christine, Bill. "Filly May Give Lukas Run for Roses: Winning Colors Wins Santa Anita Oaks by Eight Lengths" https://www.latimes.com/archives/la-xpm-1988-03-14-sp-611-story.html Los Angeles Times 14 March 1988

Christine, Bill. "A Filly Runs Them Silly in Santa Anita Derby: Winning Colors Rolls to 7 1/2 Length Victory" https://www.latimes.com/archives/la-xpm-1988-04-10-sp-1622-story.html

2019 Santa Anita Derby Media Guide. https://www.santaanita.com/wp-content/uploads/2019/03/SA-Derby-MG-web-2019-FINAL.pdf