Best Longshots for the 2026 Kentucky Oaks

A full field of three-year-old fillies has been assembled for Friday’s $1.5 million Kentucky Oaks (G1) at Churchill Downs.

There doesn’t appear to be a huge amount of separation with many of the sophomores in the ultra-competitive affair, but so many in the field have early speed and prefer to be involved in their races from the break, which leads me to believe that the winner will make a late run in the stretch en route to Oaks glory. I’ll tab a pair of ladies who will benefit from the shape of the race.

2026 Kentucky Oaks best longshots

#10 Prom Queen (8-1)

Prom Queen, my top pick, broke her maiden with emphasis at Gulfstream Park in her second lifetime appearance prior to rallying in the lane to post another impressive score in the Gulfstream Park Oaks (G2) in her stakes debut. Trained by Brad Cox for Gray and Mary West, the Quality Road filly did flash pace in her debut run but has since rated from off the tempo and kicked for home late, and her running style seems ideal for this particular contest. 

The homebred has earned Brisnet Late Pace ratings of 95 and 100 from her pair of two-turn tilts in advance of the Oaks, and getting additional ground with which to work with on Friday will be to her benefit. Prom Queen has a nice draw towards the outside to secure a potentially clear, ideal trip behind swift, contested fractions, with Javier Castellano retaining the mount. 

#9 Always a Runner (10-1)

Always a Runner has a very high ceiling and comes off an impressive score in the Gazelle (G3) at 1 1/8 miles at Aqueduct. Trained by Chad Brown, the seven-figure yearling purchase was not very professional once clear in the stretch while making her second run in that score, but she made two different moves to reel in a clear leader late who appeared to be well on her way to a victory, nonetheless. 

The dark bay daughter of the superb Gun Runner could possibly be a bit too ‘green’ to win a race of this magnitude at this stage of her development, but the talent is undoubtedly there, and I feel that she will receive a great setup to showcase her considerable ability in the latter stages of the tilt. Jose Ortiz will guide the Kentucky-bred for the initial time.