2023 Kentucky Oaks preview and best bets

By Adam Burke  (VSiN.com senior reporter) 

May 3, 2023 10:40 PM


Race 11 of 14 on Friday at Churchill Downs in Louisville, Kentucky features some of the best three-year-old fillies in the racing world. The 2023 Kentucky Oaks is a 1 1/8-mile Grade I race with a purse of $1.25 million and a first-place prize of $750,000 to go along with a garland blanket of lilies for the winning horse.

The 129th running of the Oaks has a field of 14 and should feature plenty of excitement with a large crowd, as this race is annually outdrawn by only the Kentucky Derby and Preakness Stakes. Post time is at 5:51 p.m. ET on Friday, May 5.

Here are the horses, trainers, jockeys, and odds for the 2023 Kentucky Oaks:







Mimi Kakushi

S. bin Ghadayer

M. Barzalona



The Alys Look

B. Cox

J. Castellano



Gambling Girl

T. Pletcher

I. Ortiz Jr.




N. Casse

R. Gutierrez



Wonder Wheel

M. Casse

J. Rosario




B. Cox

C. Landeros



Wet Paint

B. Cox

F. Prat



Promiseher America

R. Handal

J. Vargas Jr.



And Tell Me Nolies

Peter Miller

R. Vazquez



Flying Connection

T. Fincher

F. Geroux



Defining Purpose

K. McPeek

B. Hernandez Jr.



Dorth Vader

M. Yates

L. Saez



Affirmative Lady

G. Motion

J. Velazquez



Pretty Mischievous

B. Walsh

T. Gaffalione



Taxed (ae)

R. Morse

R. Bejarano



Julia Shining (ae)

T. Pletcher

L. Saez



Hoosier Philly (ae)

T. Amoss

E. Morales


(ae) = Also Eligible in the event of scratches

Wet Paint is the clear favorite at 5-2 from the 7 post, while Botanical is right next door in the 6 post at 4-1. Otherwise, the race appears to be wide-open with several double-digit shots. There is a 40% chance of showers on Friday, so the track could be a little muddy, but no rain is forecast up until Friday, so it could be dry and fast if Mother Nature holds up her end of the bargain.

The forecast matters a lot in any horse race, but especially this one, which has typically held a noticeable speed bias. Three of the last four winners were first or second at the half-mile. Abel Tasman came from well off the pace on a sloppy track in 2017, but she is the only filly since 2013 to come from more than five lengths back. That was also the only time since 2008 that the course has been noticeably sloppy.

Here are some quick handicaps on the 14 horses scheduled to be in the field.

1. Mimi Kakushi (20-1): Mimi Kakushi last ran in the UAE Oaks back on Feb. 17 and won that Grade III race at Meydan as the 7-5 favorite by 1 1/4 lengths over the second favorite, Ami Please. It was a strong run on a 1 3/16-mile track, but the field is quite a bit stronger here. Also, she draws the No. 1 post from which Secret Oath won last year, but that was the first top-three finish from that post since 2004. 

2. The Alys Look (15-1): Similarly, The Alys Look drew a tough starting position, as the No. 2 post has only hit the trifecta board once in almost 20 years of the Oaks. The Alys Look is overshadowed in a big way by favorite Wet Paint and second favorite Botanical from the Brad Cox stable. Cox won in 2018 with Monomoy Girl and in 2020 with Shedaresthedevil. She finished third in the five-horse Fair Grounds Oaks behind Southlaw and Pretty Mischievous at 4-1 odds, falling back late in the 1 1/16-mile race.

3. Gambling Girl (15-1): Todd Pletcher’s lone entry (barring multiple scratches) is Gambling Girl, the daughter of Dialed In and Tulipmania. She ran a strong second in the Gazelle Stakes at Aqueduct at this length back on Apr. 8, coming up just short to Promiseher America, who won at 26-1 closing odds. Gambling Girl got a bad start and got caught in traffic, but she made a big move in the six-horse race with a great push from Jose L. Ortiz. She had a wide run around the final turn and finished a half-length behind. She looks like a strong closer with Irad Ortiz Jr. on the mount. Pletcher won in 2013 with Princess of Sylmar, a closer reminiscent of this filly, at 39-1.

4. Southlawn (8-1): Trainer Norm Casse has found some success with fillies in stakes races. Southlawn won the Gr. 2 Fair Grounds Oaks and he also had winners with Super Quick in the Allaire DuPont Distaff Stakes at Pimlico last year on Preakness weekend and also a Gr. 3 Schuylerville Stakes win with Pretty Birdie in 2021. The son of Hall of Famer Mark Casse has a good speed horse here in the daughter of Pioneerof the Nile and Mo d’Amour. Pioneerof the Nile sired American Pharoah and Mo d’Amour ran in the 2016 Kentucky Oaks to a fifth-place finish at 30-1.

Fourteen of the last 16 fillies to win the Kentucky Oaks had won a graded stakes race previously and Southlawn fits the bill. She’ll be a popular filly to win and also as a complement with Wet Paint in exotics.

5. Wonder Wheel (12-1): Mark Casse’s lone entry draws the post just outside of his son’s promising contender. Wonder Wheel, sired by Into Mischief, has gone 0-for-2 since winning the Breeders’ Cup Juvenile Fillies at Keeneland last November. She was second in the Suncoast Stakes in Tampa and failed to hit the board last month in the Gr. 1 Ashland Stakes at Keeneland. That was with Tyler Gaffalione, but Casse will have Joel Rosario in the irons here. She was underwhelming in the Ashland and tried to make a push with a wide run on the final straightaway, but Gaffalione pulled her back. With the longer length here, it’s a big ask to be in contention.

6. Botanical (4-1): The daughter of Medaglia d’Oro and Daisy has won four straight races by a combined 24 1/2 lengths, but she draws a much better field now and a full-fledged dirt track. Running out of Turfway Park, she started as a turf horse but moved to the synthetic surface to win the Cincinnati Trophy and the Bourbonette Oaks just three weeks apart. Chris Landeros was in the mount for both wins and assumes the position here as well. Botanical was the even-money favorite in the win in the Bourbonette and went wire-to-wire, but the surface and the potential weather are tricky elements of the handicap. She did run away from the field over the final furlong, which means the extra 1/8th mile may not bother her at all.

7. Wet Paint (5-2): Godolphin owns a lot of winning horses and this could be another one to add to the list. The favorite is peaking at the right time off of a spectacular performance in the Gr. 3 Fantasy Stakes, which marked her third straight stakes win. She was the 3/5 favorite in the Fantasy and was 12 lengths back at the first quarter mile before winning running away. She swept all three filly stakes at Oaklawn, with wins in the Honeybee and also Martha Washington. The daughter of Breeders’ Cup Classic winner Blame and stakes winner Sky Painter has run at 1 1/16 miles in each of the last three races and shown incredible speed late, so the distance upgrade should not be a problem. Trainer Brad Cox is also really good in this race.

8. Promiseher America (30-1): Promiseher America was sired by American Pharoah, so we know she has the bloodline to win a big race. The Raymond Handal-trained filly came in at 26-1 in the Gazelle with a really strong run front-to-back and had just enough to hold off Gambling Girl’s late charge. It was only her fourth race and her stakes debut. Her speed figures aren’t on par with the top contenders in this race, but she’s a late bloomer and she’s one of the few in this race to have run at the 1 ⅛-mile distance.

9. And Tell Me Nolies (15-1): The daughter of Arrogate and Be Fair has regularly hit the board, finishing first or second in five of the last six races, with the lone miss being last year’s Breeders’ Cup Juvenile Fillies with a disappointing eighth-place finish. However, And Tell Me Nolies has finished second to Faiza in both the Santa Ysabel and the Santa Anita Oaks. She’ll be back in bluegrass country for the first time since that trip to Keeneland last November after winning the Del Mar Debutante and Chandelier Stakes prior to facing off with the best two-year-old fillies in the nation. She was beaten badly by Faiza in both races and has topped out at 88 with her Equibase Speed Figure. The lowest winning mark in the last 20 years has been a 98.

10. Flying Connection (15-1): It is interesting to see Florent Geroux on the mount for Flying Connection instead of one of the Brad Cox horses, given that Geroux and Cox teamed up in 2018 and 2020 for victories. Instead, he’ll ride the Todd Fincher filly and daughter of Nyquist, who won the 2016 Kentucky Derby after winning the 2015 Breeders’ Cup Juvenile. Her speed figures have gone up in each of the last three races and she’s won four of the last five, including the Sunland Park Oaks back on Mar. 26, albeit over a weak field. She has only run one race over a mile and has a wider trip here with an outside post.

11. Defining Purpose (12-1): Kenneth McPeek took this horse back to Kentucky after a couple of runs at Oaklawn Park that were won by Wet Paint. The move paid off, as Defining Purpose won the Ashland Stakes and came in at better than 20-1. She’s a boom or bust horse for McPeek, who was second in 2020 at the Oaks with Swiss Skydiver, who then went on to win the Preakness Stakes. Her big run back at Keeneland was easily her top speed figure, but you wonder if she has it in her to level up again.

12. Dorth Vader (20-1): Cashing at nearly 47-1 in the Davona Dale Stakes put Dorth Vader on the map, but she’s a long shot for a reason in this one. Jockey Luis Saez is looking to be the first back-to-back winner in the Kentucky Oaks since legendary rider Eddie Arcaro won three straight from 1951-53. Saez won last year for D. Wayne Lukas aboard Secret Oath (6-1), but this horse doesn’t have the same burst or closing speed. The only other really noteworthy win for Dorth Vader came at just six furlongs in the Sandpiper last December in Tampa.

13. Affirmative Lady (10-1): Sometimes all it takes is a change of scenery. Affirmative Lady went south for the spring and won back-to-back races at Gulfstream Park, including the Gr. 2 Gulfstream Park Oaks on April 1 at a 10-1 price. Saez had an excellent ride and, oddly enough, pulled away from Dorth Vader to win that race, but John Velazquez draws the mount here. Velazquez is elite in his own right and won on Malathaat in 2021 for Pletcher, but it is interesting to see Saez take Dorth Vader, while Velazquez returns to ride after running Affirmative Lady in all three races last year.

14 Pretty Mischievous (10-1): Pretty Mischievous has hit the board in all six races, including a win in February in the Gr. 2 Rachel Alexandra Stakes. She couldn’t keep pace with Southlawn during the final stretch of the Gr. 2 Fair Grounds Oaks, which undoubtedly lowered her perception here. The bloodline is good with Tapit-sired Pretty City Dancer and Into Mischief, who has certainly made a name for himself as a racehorse and as a sire. She has a long trip on the outside, but she’s consistently run against good competition and has enough speed to be a factor. 

Alternates: If there are two defections from the race, Julia Shining might be a really interesting horse to throw into exotics or take as a long shot to win. She’s kind of untested, but she’s the sister of Malathaat with a sire you may have heard of named Curlin. She’s a lightly-raced Todd Pletcher filly that was third in the Suncoast and the Ashland, but her pedigree is quite strong and Saez is expected to ride her if she gets in for the four-time Oaks winner Pletcher.


Botanical might be a last-minute call, as a wet and sloppy track feels like a huge downgrade to her chances. Wet Paint (7) and Southlawn (4) are the two I like the most, with a look at Pretty Mischievous (14) in exotics and as a longer shot to win. If the track holds up or the rain holds off, Botanical (6) should be included in exotics.

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