2023 Kentucky Oaks Predictions and Race Analysis

by Joey House - 5/1/2023

You can describe the 2022 Kentucky Oaks with one phrase: "D. Wayne does it!," as Hall of Fame trainer D. Wayne Lukas tied Woody Stephens for the most Oaks victories at five.

Friday's Kentucky Oaks edition features 14 entrants, and this 1 1/8 mile race is going to be very entertaining. If you didn't notice, 10 horses are listed at 15-1 or higher. And with the weather predicting a 30% chance of thunderstorms, it's possible that we could see a long shot hit the board. Here are the highlights of the field and some predictions (Odds are the morning line track odds).

1. Mimi Kakushi (56-1)

Trainer: Salem bin Ghadayer, Jockey: Mickael Barzalona

She has been impressive in the UAE, winning both the (LS) UAE 1000 Guineas and (G3) UAE Oaks. Unfortunately, there has never been a UAE Oaks winner to triumph in the Kentucky Oaks. Someday that will change, but until it does, I will stay away from the UAE imports.

2. The Alys Look (40-1)

Trainer: Brad Cox, Jockey: Luis Saez

Brad Cox has three fillies in the Oaks, and this one features the longest odds of the group. While she finished in third last time out, she mounted a bold comeback to finish in third. I think that Saez learned from that race and will keep The Alys Look closer to the front, so when she makes her bid, it won't be from such a distance.

3. Gambling Girl (20-1)

Trainer: Todd Pletcher, Jockey: Irad Ortiz Jr.

While she hasn't stood in the winners' circle since last September, Gambling Girl has been in the mix in each of the five races since. They were all stakes, with three of them being graded, so she's faced the toughest competition and is capable of giving a strong showing for herself. Her pedigree indicates strength in route races. And with 4-time Eclipse winner Ortiz, Jr on her mount, she may not win but could provide very attractive prices for exotics.

5. Southlawn (12-1)

Trainer: Norm Casse, Jockey: Rey Gutierrez

While it took Southlawn a few tries to find the surface and distance that suited her, she appears to have her wheelhouse. She won the aforementioned (G2) Fair Grounds Oaks in impressive fashion, catching and pulling away from Pretty Mischievous to win by 3 1/4 lengths. Don't expect her prices to be this high on Friday.

6. Botanical (9-2)

Trainer: Brad Cox, Jockey: Chris Landeros

Unlike the previous horse, Botanical has speed to burn, posting a 112 in her most recent win in the Tampa Bay Bourbonette Oaks. The main question is if her form on the synthetic surface at Turfway will carry over to the natural dirt at Churchill. Her pedigree points to a “yes,” being sired by multiple Grade 1 dirt route winner Medaglia d'Oro and damsire Blame, winner of the 2010 Breeders' Cup Classic. Just enough intrigue to make things interesting.

7. Wet Paint (3-1)

Trainer: Brad Cox, Jockey: Flavien Prat

Winner of two straight (G3) stakes races, this prodigious filly has proven very adept on dirt, but not so much on turf. In the (G3) Fantasy on April 1, she fooled everyone by coming from dead last halfway through to win by two lengths. The mile and an eighth will suit her just fine.

8. Promiseher America (20-1)

Trainer: Ray Handal, Jockey: TBA

Uninspiring in her first two starts in sprint races, Promiseher America seems to have found her niche in distance. Stretching out to a mile, the daughter of Triple Crown winner American Pharoah broke her maiden with a powerful 6 1/4-length triumph. Moving up to the (G3) Gazelle Stakes, she surprised everyone as a 26.5-1 winner. She's improving as she goes along and provides an interesting option with long odds.

9. And Tell Me Nolies (40-1)

Trainer: Peter Miller, Jockey: Ramon Vazquez

She had a great 2-year-old season, winning the (G1) Del Mar Debutante and (G2) Chandelier at Santa Anita. However, that was last October, and she hasn't returned to the winners' circle since. The lowest Equibase Speed Figure to win in the past 20 runnings of the Oaks was a 98, which is 10 points higher than her career best. I'm telling you the truth when I say to pass on her.

10. Flying Connection (25-1)

Trainer: Todd Fincher, Jockey: Florent Geroux

Starting off her career at Del Mar, she was overwhelmed by her competition. Todd Fincher relocated her to New Mexico, and she's thrived, winning four out of five. She's returned some impressive speed ratings, which give her credibility, but you have to wonder how going up in class again is going to affect her. The jury is out on that, and so am I.

11. Defining Purpose (8-1)

Trainer: Kenny McPeek, Jockey: Brian Hernandez Jr.

Defining Purpose is like Aaron Judge: She either hits a home run or strikes out. She has won three races and finished off the board in three others, with a third-place finish as well. She's already lost to Wet Paint twice this year, and I believe it'll happen again.

12. Dorth Vader (30-1)

Trainer: Mike Yates, Jockey: TBA

While she possesses the greatest name in the field, Dorth Vader is going to have to tap into "The Force" if she wants to win this race. She won the (G2) Davona Dale in March but finished off the board in 4th in the (G2) Gulfstream Park Oaks on April Fools Day. Pass

13. Affirmative Lady (20-1)

Trainer: Graham Motion Jockey: John Velazquez

Reunited with jockey Velazquez, who rode her for all three races in 2022, Affirmative Lady will need a much bigger effort than she's shown so far in speed ratings to get into the winners' circle. She has been improving, however, and won the (G2) Gulfstream Park Oaks against some of her competition here.

14. Pretty Mischievous (18-1)

Trainer: Brendan Walsh Jockey: Tyler Gaffalioine

Winner of the Fair Grounds Untapable and (G2) Rachel Alexandra, Pretty Mischievous looked to be flying high until she was run down by Southlawn in the (G2) Fair Grounds Oaks. With that hiccup aside, she has the class and tactical speed to make her a contender with very attractive odds.

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