Casual horse racing fans are well-acquainted with the Kentucky Derby, a mainstay of the first Saturday in May. But the Kentucky Oaks, Churchill Downs' annual feature on the first Friday in May, deserves its flowers as well — lilies, to be exact.
A field of 14 three-year-old fillies will go 1 1/8-miles at the historic Louisville oval on May 2, but only one will take down the $1.5 million purse. The majority of the wagering public will likely side with 6-5 morning-line favorite Good Cheer, who is 6-for-6 lifetime heading into the Kentucky Oaks, but I'm here to tell you what long shots I like to upset the apple cart with my early betting picks.
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Kentucky Oaks prediction: Take Charge Milady
No. 10 Take Charge Milady (12-1) looks to be the best of the deep closers in the 2025 Kentucky Oaks, and that running style looks like the preferred one here.
From the inside out, Simply Joking, Fondly, La Cara, Five G, Tenma, Anna's Promise, and Quietside all look like they could show at least some speed on Friday afternoon. It only takes a couple of them going hell-for-leather early to set up a pace that could melt down in the homestretch.
Take Charge Milady began the 2025 season with two wins from two starts, crushing maidens at Oaklawn Park before drawing off in the Martha Washington Stakes. Her first graded stakes try came in the Grade III Honeybee two-back but she never had a chance after getting sawed off at the start.
Last time out, Take Charge Milady bounced back impressively to take second in the Grade I Ashland Stakes behind La Cara. The extra 1/16th-mile she'll get on Friday could help make up the difference on that rival and put her over the top of the entire field.
Take Charge Milady is represented by the same connections that took last year's Kentucky Oaks with eventual 2024 Horse of the Year in Thorpedo Anna — trainer Ken McPeek and jockey Brian Hernandez Jr.
Kentucky Oaks pick: Take Charge Milady (12-1 at FanDuel Racing)
Kentucky Oaks long shot predictions
Simply Joking
I am hopeful that the jockey change to Florent Geroux on No. 2 Simply Joking (10-1) will result in a change in tactics with this daughter of Practical Joke.
Simply Joking came from off the pace to score in her debut at Fair Grounds, but she's gone to the lead in each of her last two starts. She made every pole a winning one in the Silverbulletday Stakes two-back but was unable to hold off Quietside in the Grade II Fantasy Stakes when last seen.
This Whit Beckman trainee is the lightest-raced filly in the field with just the three starts under her belt, so the upside is definitely there. She's training extremely well at Churchill for this start.
Kentucky Oaks long shot pick: Simply Joking (10-1 at FanDuel Racing)
Anna's Promise
I've seen far worse 30-1 shots than No. 12 Anna's Promise. This daughter of Promises Fulfilled was toiling in the maiden ranks through five starts before switching to the Carlos David barn. In three starts since, she's picked up the maiden diploma, beaten allowance/optional claiming foes, and run second in the Grade II Gulfstream Park Oaks.
The speed figures have improved dramatically in her sophomore season, and they're not far off where they need to be to take this race, let alone hit the board. Although Anna's Promise wasn't Luis Saez's first choice (he understandably lands on Good Cheer), Junior Alvarado has ridden her to victory before and regains the mount.
Kentucky Oaks long shot pick: Anna's Promise (30-1 at FanDuel Racing)
2025 Kentucky Oaks odds
The Kentucky Oaks is Race 11 on the Churchill Downs program for Friday, May 2, and post time is scheduled for 5:51 p.m. ET. USA Network will have live coverage.
| Post | Horse | * |
** |
|
|---|---|---|---|---|
| 11 | Good Cheer | +120 | 6-5 | +120 |
| 7 | La Cara | +600 | 6-1 | +600 |
| 14 | Quietside | +800 | 8-1 | +800 |
| 2 | Simply Joking | +1000 | 10-1 | +1000 |
| 6 | Ballerina d'Oro | +1000 | 10-1 | +1000 |
| 8 | Five G | +1200 | 12-1 | +1200 |
| 9 | Tenma | +1200 | 12-1 | +1200 |
| 10 | Take Charge Milady | +1200 | 12-1 | +1200 |
| 3 | Fondly | +2000 | 20-1 | +2000 |
| 1 | Early On | +3000 | 30-1 | +3000 |
| 4 | Drexel Hill | +3000 | 30-1 | +3000 |
| 5 | Quickick | +3000 | 30-1 | +3000 |
| 12 | Anna's Promise | +3000 | 30-1 | +3000 |
| 13 | Bless the Broken | +3000 | 30-1 | +3000 |
*FanDuel Racing odds available in AZ, CO, IL, IN, KY, LA, MA, MD, MI, NY, OH, PA, VA, WV, WY
**bet365 Kentucky Derby odds are not available in the United States
