Top 3 picks and longshots in the Kentucky Oaks

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Jen Caldwell

May 4th, 2018

Wonder Gadot (left) and Monomoy Girl (right) readying for the Kentucky Oaks at Churchill Downs (c) Churchill Downs/Coady Photography

The Kentucky Oaks (G1) doesn't grab as much attention as the Kentucky Derby (G1), but there are just as many opportunities to hit it big with the girls as there is with the boys.

This year's Run for the Lilies features a pair of stand-out favorites, which means plenty of good prices on everyone else. First up, though, my top three picks.


  1. As much as I like Midnight Bisou, I think MONOMOY GIRL (#14) has the Kentucky Oaks wrapped up. The Brad Cox trainee has experience winning over the track; experience on big days, thanks to her 5 1/2-length romp in the Ashland Stakes (G1) at crowded Keeneland; and experience in dealing with off conditions, though that did take place on turf at Indiana Grand in her debut. The chestnut daughter of Tapizar will be trying nine furlongs for the first time on Friday while making only her third start of the year, but nothing has fazed Monomoy Girl yet and I don't expect her to falter under jockey Florent Geroux.
  2. MIDNIGHT BISOU (#10) rides a three-race win streak into the Kentucky Oaks, all of which came in stakes. In fact, the Bill Spawr pupil has yet to win anything else, breaking her maiden in the Santa Ynez Stakes (G2), taking the Santa Ysabel Stakes (G3) next out and wrapping up the graded hat track with a 3 1/2-length triumph in the Santa Anita Oaks (G1) last out on April 7.The Midnight Lute filly earned a career-best 96 BRIS Speed rating for that latter effort which, while not aweinspiring, continues her form of improvement with each start. Sometimes steady progression is what it takes to win on the big day and Midnight Bisou can only benefit from a gradual build up. Of course, having Mike Smith in the irons doesn't hurt her chances either.
  3. While listed at 15-1 on the morning line, RAYYA may end up taking a lot of action. The Tiz Wonderful filly makes her stateside debut in the Oaks after beginning her career in Dubai at Meydan with trainer Doug Watson. There, the chestnut lass ran second in the U.A.E. One Thousand Guineas before romping by 3 3/4 lengths in the U.A.E. Oaks (UAE-G3). She then tried the boys in the U.A.E. Derby (UAE-G2) and proved best of the rest as Kentucky Derby contender Mendelssohn ran off to dominate by 18 lengths. Rayya was subsequently sent to the United States and transferred to trainer Bob Baffert, for whom she posted a couple of works at Santa Anita Park, including a six-furlong bullet move in 1:12.80 on April 21. Not only does Rayya have a good shot at the upset, she could also give an indication of how well Mendelssohn will fare one day later. Drayden Van Dyke will be in the irons for the first time on Friday.


WONDER GADOT (#5) has not managed to find the winner's circle as much as her connections would probably like, but the consistent filly is still a major contender, despite her 20-1 morning line. The dark bay daughter of Medaglia d'Oro is 0-2-2 on the year from four starts, but her latest effort saw the Mark Casse charge just miss by a nose in the Fantasy Stakes (G3) at Oaklawn Park. A little more ground and she might have got the win. In fact, Wonder Gadot is one of only three fillies in this year's Oaks with prior experience at or over the 1 1/8-mile distance. She captured the Demoiselle Stakes (G2) going nine furlongs last year by 3 3/4 lengths and could utilize that familiarity with the extra distance to prevail on Friday. John Velazquez has the call.

MY MISS LILLY (#11) is actually listed at 10-1 on the morning line, lower than Rayya, but I'm putting her in the longshots because she might not garner the same attention the Dubai filly will. Nonetheless, the gray daughter of Tapit should not be overlooked in the Oaks. Rayya, Wonder Gadot and My Miss Lilly are the three fillies who have run, and won, at the distance or beyond. My Miss Lilly did so in the Gazelle Stakes (G2) last out at Aqueduct, getting up in the stretch and gutting out the half-length victory under returning rider Joe Bravo. The Mark Hennig lass will need to prove her tenaciousness once again if she wants to wear the lilies on Friday, but has the talent to do just that.