LOUISVILLE – Almost every time an exceptional filly comes along, her owner and trainer have at least fleeting thoughts about running her against colts in the Kentucky Derby instead of against other fillies in the Kentucky Oaks. In the 140 years that both races have been run, 39 fillies have run in the Derby and three have won – Regret in 1915, Genuine Risk in 1980 and Winning Colors in 1988.
Which gives us a great trivia question: In the three years a filly won the Derby, who won the Oaks? The answer is Waterblossom in 1915, Bold n' Determined in 1980, and Goodbye Halo in 1988. If anybody out there uses this information to win a bar bet, you can mail me a check care of WAVE3.com.
A gambling horseman is more likely to take a Derby shot with a filly when the field of colts looks mediocre. That's why D. Wayne Lukas ran Winning Colors in the Derby instead of the Oaks. Plus, the big roan met his other criteria: She was exceptionally talented and had the tactical field to stay out of trouble in the larger Derby field.
Tactical speed? Heck, Winning Colors stayed out of trouble by going right to the lead and staying there. The big roan began to tire inside the eighth pole and was almost caught by the fast-closing Forty Niner. However, jockey Gary Stevens did a masterful job of getting her to hold on for a nose victory.
This year the field of Derby colts looks so talented and deep that it would have been silly to try to get a filly eligible for the 20-horse field. Besides, the Oaks has grown in popularity over the last 15 years, at least partly due to Churchill's decision to use the day to honor survivors of breast cancer. There's a parade of survivors between races in the middle of the day, and everyone is encouraged to wear pink. The Oaks crowds now surpass the 100,000 mark and seem to get bigger every year.
Sometimes an owner with a great Oaks-winning filly is apt to be second-guessed after the Derby. Did the owner underestimate the filly? Should he (or she) have taken a shot at the roses instead of the garland of lilacs? A classic example is what happened with the fast and talented Silverbulletday in 1999. (Yes, she got her name from what Coors beer fans like to call their favorite beverage).
Her trainer, Bob Baffert, came to the 1999 Run for the Roses on one of the more incredible rolls in Derby history. He made his Derby debut in 1996 with Cavonnier, who lost to Grindstone in a photo finish. Then the white-maned one captured the Derby twice in a row with Silver Charm in 1997 and Real Quiet in 1998. (Both also won the Preakness, but had their Triple Crown dreams dashed in the Belmont Stakes.)
Now here he was in 1999 with two promising fillies (Silverbulletday and Excellent Meeting), a good colt (Prime Timber) and a tough gelding (General Challenge). After thinking about where to put his fillies, Baffert finally decided to run Silverbulletday in the Oaks and Excellent Meeting in the Derby. Had he switched that decision, today we might be talking about four filly winners of the Derby instead of three.
The Derby was won by the longshot Charismatic, with Prime Timber finishing fourth, Excellent Meeting fifth, and General Challenge 11th in the 19-horse field. But with all due respect to Charismatic, he didn't light up Churchill Downs the way Silverbulletday did in the Oaks.
Suffice it say that she won the Oaks laughing. Stevens, the same jock who had ridden Winning Colors, never touched her with his whip and wrapped up on her down the stretch. She was simply brilliant.
In Baltimore two weeks later, both Silverbulletday and Charismatic won again, the filly taking the Black-Eyed Susan Stakes and the Derby winner prevailing a day later in the Preakness. Once again, however, the filly impressed more racetrackers than the colt.
So Baffert finally changed his mind and decided to give Silverbulletday the opportunity to deny Charismatic's Triple Crown in the Belmont. She went to the lead, as was her style, and set the pace for the first three-quarters, but then began to fade. Maybe she was tired from her previous two efforts and maybe not. Whatever, she faded to seventh behind the victorious Lemon Drop Kid.
Even so, she fared better than Charismatic. He injured a foreleg and had to be pulled up in the stretch. Jockey Chris Antley jumped out of the saddle and cradled the injured leg until the ambulance arrived – one of the more endearing portraits in Triple Crown history.
The last filly to run in the Derby was Eight Belles in 2008. She finished a game second to Big Brown, but made a bad step while cooling down on the backstretch and was humanely destroyed. That inspired protests by animal-rights activists and a lot of soul-searching by industry leaders.
This year Larry Jones, who trained Eight Belles, has two excellent chances to upset 7-to-2 favorite Stellar Wind in the141st Oaks. He trains both I'm a Chatterbox, the co-second choice at 4-to-1, and Lovely Maria, the fourth pick at 4-to-1. The Churchill crowd probably will be heavily on Lovely Maria, who won the Ashland Stakes on April 4 at Keeneland for former Gov. Brereton Jones.
It's an evenly matched bunch, but your humble correspondent is picking Lovely Maria and the longshot Forever Unbridled to finish 1-2. Whatever happens, you can bet the winning Oaks owner, whomever he or she might be, won't be second-guessing the decision after what could be a Kentucky Derby for the ages.
Billy Reed is a longtime sportswriter who contributes occasional columns for WAVE3.com.