Kentucky Oaks 2023 Betting Guide: Wet Paint Set as Favorite After Post Position Draw

The Kentucky Oaks is the most prestigious and lucrative race for 3-year-old female horses in the country. The sister race to the Kentucky Derby is worth $1.25 million and is set to be run today, Friday, May 5 at Churchill Downs, one day before the first leg of the Triple Crown.

Post time for the Oaks is 5:51 p.m. ET. USA and Peacock have television coverage beginning at 1 p.m. ET.

The Kentucky Oaks is contested over a distance of 1 1/8 miles and has been won by such champions as Rags to Riches (2007), Rachel Alexandra (2009), and Malathaat (2021). Last year’s winner, Secret Oath, gave Hall of Fame trainer D. Wayne Lukas a record-tying fifth Kentucky Oaks victory.

The post positions and odds for the 2023 Kentucky Oaks were drawn at Churchill Downs on May 1. Now that the fields are set, our 2023 Kentucky Oaks betting guide has all you need to know about who the top contenders are in this year’s field and which fillies are worth wagering on.

Main event: 2023 Kentucky Derby Field | Kentucky Derby odds

2023 Kentucky Oaks Post Positions and Odds

Here is the field for Friday’s Kentucky Oaks.

Who is the Favorite for Kentucky Oaks 149?

Wet Paint, unbeaten in three starts in 2023, was made the 5-to-2 morning-line favorite for the 2023 Kentucky Oaks. Trained by Brad Cox, Wet Paint comes into the Kentucky Oaks off a victory in the Grade 3 Fantasy Stakes on April 1, a race in which she rallied from last in the 10-horse field to win by 2 1/2 lengths.

Wet Paint is aiming to give Cox his third career Kentucky Oaks victory. Cox previously won the race with Monomoy Girl in 2018 and Shedaresthedevil in 2020.

How Can I Bet on the Kentucky Oaks?

FanDuel, an official sports wagering partner of the Kentucky Derby, is the only sportsbook where fans can place a bet on the 2023 Kentucky Oaks and Kentucky Derby.

FanDuel is the first and only sportsbook to offer wagering on horse racing alongside traditional sports book wagering with a single account and single wallet, allowing customers to wager on the Kentucky Derby, the Kentucky Oaks, and all the races from Churchill Downs on Oaks and Derby Days. Racing fans will be able to find bet options for the Kentucky Derby in just a few taps when they open the FanDuel app and then click the horse racing icon.

To celebrate the first year of the partnership with Churchill Downs, FanDuel will offer a “$20 No Sweat Bet” to all new and existing sportsbook and DFS customers.

Get to Know the 2023 Kentucky Oaks Field

Two of the last four editions of the Kentucky Oaks have offered great payouts. In 2019, 13-1 shot Serengeti Empress bested 38-1 long shot Liora to get the win. In 2020, Shedaresthedevil rewarded those who backed her at 15-1 odds by earning a 1 1/2-length triumph.

This year’s Kentucky Oaks field looks to be a wide-open affair with plenty of potential for big prices. We evaluate all of the Kentucky Oaks entrants to see which fillies offer the best wagering potential.

PP. 1 Mimi Kakushi (Bay Filly)

• Sire: City of Light
• Dam: Rite Moment, by Vicar
• Trainer: Salem bin Ghadayer
• Owner: Sheikh Hamdan bin Mohammed Al Maktoum
• Jockey: Mickael Barzelona
• Record and earnings: 5-3-0-0, $212,701
• Morning Line Odds: 20-1
• Last Race: Won Grade 3 UAE Oaks by 1 1/4 lengths.
• Why You Should Bet Her: This Dubai-based filly has prevailed in her last three starts including the UAE One Thousand Guineas at Meydan Racecourse on Jan. 20 and the UAE Oaks on Feb. 17, where she defeated the Doug O’Neill-trained Ami Please.
• Why You Should Save Your Money: Mimi Kakushi hasn’t started since that UAE Oaks victory in February and the final time for that race was a pedestrian 2:00.01 for 1 3/16 miles.
• What They’re Saying: “She was a professional filly from the beginning, especially in her mind, and she’s very easy to train. She knows she must give everything in a race.” – Trainer Salem bin Ghadayer.

PP. 2 The Alys Look (Bay Filly)

• Sire: Connect
• Dam: Foul Play, by Harlan’s Holiday
• Trainer: Brad Cox
• Owner: Dawn and Ike Thrash
• Jockey: Luis Saez
• Record and earnings: 6-2-1-2, $190,528
• Morning Line Odds: 15-1
• Last Race: Third in Grade 2 Fair Grounds Oaks
• Why You Should Bet Her: Beat her well-regarded stablemate Chop Chop by a length in the Silverbulletday Stakes at Fair Grounds on Jan. 21. Has only been off the board once in six starts.
• Why You Should Save Your Money: Her worse career race came at Churchill Downs when she was seventh in a maiden special weight race in October. Hasn’t yet gotten over the hump against the more talented members of her division.
• What They’re Saying: “The Alys Look has that one race at Churchill in the mud with blinkers on, she was rank early, you’ve got to draw a line through that race. She’s a good filly. She really showed some determination and grit the last sixteenth of a mile (in the Silverbulletday).” – Trainer Brad Cox.

PP. 3 Gambling Girl (Bay Filly)

• Sire: Dialed In
• Dam: Tulipmania, by Empire Maker
• Trainer: Todd Pletcher
• Owner: Repole Stable
• Jockey: Irad Ortiz Jr.
• Record and earnings: 9-2-2-2, $257,410
• Morning Line Odds: 15-1
• Last Race: Second in Grade 3 Gazelle Stakes
• Why You Should Bet Her: Has held her own against stakes company, placing in the top three in the Grade 2 Demoiselle, Busanda Stakes, and Gazelle.
• Why You Should Save Your Money: Has lost five straight races with her last victory coming in the Joseph A. Gimma Stakes going seven furlongs at Belmont Park last September.
• What They’re Saying: “She always tries hard. I thought we had dead aim at the winner (in the Gazelle) but we just couldn’t quite get there. It was another good effort from her.” – Trainer Todd Pletcher.

PP. 4 Southlawn (Bay Filly)

• Sire: Pioneerof the Nile
• Dam: Mo d’Amour, by Uncle Mo
• Trainer: Norm Casse
• Owner: Robert Masterson
• Jockey: Reylu Gutierrez
• Record and earnings: 7-3-0-0, $318,369
• Morning Line Odds: 8-1
• Last Race: Won Grade 2 Fair Grounds Oaks by 3 1/4 lengths
• Why You Should Bet Her: Since having throat surgery to correct a minor breathing problem, Southlawn has been unbeaten in two subsequent starts. She aired out her foes when winning her seasonal debut by eight lengths at Fair Grounds in February and overhauled Pretty Mischievous in deep stretch of the Fair Ground Oaks to score a 3 1/4-length decision.
• Why You Should Save Your Money: Has yet to win in three starts at Churchill Downs but one of those efforts came on the turf.
• What They’re Saying: “I don’t think that we could be any more excited about the horse we are bringing to (the Oaks). She’s run two legitimately good races as a 3-year-old this year and I think she stacks up against anybody. I think basically there is no standout this year.” – Trainer Norm Casse.

PP. 5 Wonder Wheel (Dark Bay Filly)

• Sire: Into Mischief
• Dam: Wonder Gal, by Tiz Wonderful
• Trainer: Mark Casse
• Owner:  D. J. Stable
• Jockey: Joel Rosario
• Record and earnings: 7-4-2-0, $1,578,225
• Morning Line Odds: 12-1
• Last Race: Sixth in the Grade 1 Ashland Stakes
• Why You Should Bet Her: On paper, Wonder Wheel is the most accomplished contender in the 2023 Kentucky Oaks field having won the Breeders’ Cup Juvenile Fillies at Keeneland last November en route to being named champion 2-Year-Old Filly.
• Why You Should Save Your Money: Her two starts this year have not yielded any evidence she has progressed during her sophomore season. Followed up a second-place finish in the Suncoast Stakes with a head-scratching sixth-place run in the Ashland Stakes at Keeneland. Form-wise, she’s going the wrong way at the wrong time.
• What They’re Saying: “She’s a filly that’s very deceptive. She just covers a lot of ground. (Jockey Joel Rosario) said he couldn’t believe that she went that fast (after working four furlongs in :47.20 on April 27). But that’s her.” – Assistant trainer David Carroll.

PP. 6 Botanical (Bay Filly)

• Sire: Medaglia d’Oro
• Dam: Daisy, by Blame
• Trainer: Brad Cox
• Owners: LNJ Foxwoods and Clearsky Farms
• Jockey: Chris Landeros
• Record and earnings: 6-4-1-0, $374,410
• Morning Line Odds: 4-1
• Last Race: Won Bourbonette Oaks by 2 1/2 lengths
• Why You Should Bet Her: Led from start to finish over the synthetic track at Turfway Park to take the 1 1/16-mile Bourbonette Oaks, her fourth straight victory. Has dominated her competition since notching her first win at Turfway last November, winning those four starts by a combined 24 1/4 lengths.
• Why You Should Save Your Money: All of her victories have come over a synthetic track and her first two career starts were on turf, so it remains to be seen how her form translates on a dirt surface.
• What They’re Saying: “She’s very talented and she’s already proved that this winter at Turfway when she was perfect from four starts. Keeneland’s meet has proved to be a good stepping stone for the Turfway horses. They’ve run very well there and I think that shows the caliber of horses that stayed this winter at Turfway. That gives you a lot of confidence coming into the Kentucky Oaks.” – Jockey Chris Landeros.

PP. 7 Wet Paint (Bay Filly)

• Sire: Blame
• Dam: Sky Painter, by Street Cry (IRE)
• Trainer: Brad Cox
• Owner: Godolphin
• Jockey: Flavien Prat 
• Record and earnings: 6-4-1-0, $689,000
• Morning Line Odds: 5-2
• Last Race: Won Grade 3 Fantasy Stakes by 2 1/2 lengths
• Why You Should Bet Her: With three wins in as many starts this year, Wet Paint has been the most consistent member of a sophomore filly class that lacks a clear standout. The only time she has been worse than second came when she tried the turf in her career debut. While she has been nearly flawless closing from off the pace, she showed during a runner-up finish in an allowance race at Turfway Park last December she can rate closer if needed. 
• Why You Should Save Your Money: She has yet to be tested against Grade 1 company and as wide-open as this year’s Kentucky Oaks looks, there could be strong value found elsewhere.
• What They’re Saying: “She’s been very, very consistent. I thought her run in the Fantasy was a very good race and she came back really well. If (the track) comes up wet, she can handle it. She can take mud in her face. She’s passed all the tests we’ve thrown at her. Her first race was a throw out, but other than that she’s stepped up to the plate. You don’t have to make excuses for her.” – Trainer Brad Cox.

PP. 8 Promiseher America (Chestnut Filly)

• Sire: American Pharaoh
• Dam: Promisedyouheaven, by Unbridled’s Song
• Trainer: Raymond Handal
• Owners: Hoffman Thoroughbreds and Tom McCrocklin
• Jockey: Jorge Vargas Jr.
• Record and earnings: 4-2-1-0, $198,138
• Morning Line Odds: 30-1
• Last Race: Won Grade 3 Gazelle Stakes by a half length
• Why You Should Bet Her: Has won two of three starts this year including a 6 1/4-length maiden victory and a 26-1 upset in the Gazelle Stakes where she rated just off the pace and prevailed gamely.
• Why You Should Save Your Money: Hasn’t raced outside of Aqueduct and the quality of who Promiseher America beat in the Gazelle is suspect.
• What They’re Saying: “She’s just built like a two-turn kind of horse. This filly has done everything right since we’ve had her. I thought that from before she ran she would relish the longer distances.” – Trainer Raymond Handal.

PP. 9 And Tell Me Nolies (Bay Filly)

• Sire: Arrogate
• Dam: Be Fair, by Exchange Rate
• Trainer: Peter Miller
• Owner: Peter Redekop
• Jockey: Ramon Vazquez
• Record and earnings: 7-3-2-0, $472,800
• Morning Line Odds: 15-1
• Last Race: Second in Grade 2 Santa Anita Oaks
• Why You Should Bet Her: Has only been off the board once in seven starts, that coming when she finished eighth in last November’s Breeders’ Cup Juvenile Fillies. Faiza, who defeated And Tell Me Nolies in both the Santa Ysabel Stakes and Santa Anita Oaks, is not eligible to run in the Kentucky Oaks.
• Why You Should Save Your Money: The form of the Breeders’ Cup Juvenile Fillies has not held up thus far, so the fact she was well beaten in that group is cause for worry.
• What They’re Saying: “She’s a nice filly and we have a shot.” – Jockey Ramon Vazquez.

PP. 10 Flying Connection (Bay Filly)

• Sire: Nyquist
• Dam: Free Flying Soul, by Quiet American
• Trainer: Todd Fincher
• Owners: Brad King, Randy Andrews, Chris Coleman et al
• Jockey: Florent Geroux
• Record and earnings: 7-4-0-1, $294,700
• Morning Line Odds: 15-1
• Last Race: Won Sunland Park Oaks by 2 1/4 lengths.
• Why You Should Bet Her: The aptly-named Flying Connection indeed makes her living off her early speed, taking both the Island Fashion Stakes in February and the Sunland Park Oaks in front-running fashion. Has won four of her last five starts dating back to her maiden victory at Zia Park last November.
• Why You Should Save Your Money: All of her victories have come in New Mexico so she is taking a major step up in class in the Kentucky Oaks. Finished fifth in her first two starts at Del Mar, including a loss to fellow 2023 Kentucky Oaks contender And Tell Me Nolies.
• What They’re Saying: “I’ve liked her since she was a baby last year. I thought she was the best we had and she’s come around really nicely. She earned her way here. Probably the worse thing about her is she’s one dimensional. She wants to go to the lead and you can’t really hold her back. She’s going to be close to the lead and she’s going to fight for the lead.” – Trainer Todd Fincher.

PP. 11 Defining Purpose (Gray Filly)

• Sire: Cross Traffic
• Dam: Defining Hope, by Strong Hope
• Trainer: Ken McPeek
• Owners: Magdalena Racing, Colette Marie Vanmatre, and James Ball
• Jockey: Brian Hernandez, Jr.
• Record and earnings: 7-3-0-1, $543,688
• Morning Line Odds: 12-1
• Last Race: Won Grade 1 Ashland Stakes by a half length
• Why You Should Bet Her: Rebounded after finishing sixth over a wet track in the Grade 3 Honeybee Stakes at Oaklawn to win the Ashland Stakes in stalk and pounce fashion.
• Why You Should Save Your Money: Was handily defeated by Wet Paint in both the Martha Washington Stakes and the Honeybee, both of which were contested over wet tracks. Likely won’t love the going if it rains on Kentucky Oaks Day.
• What They’re Saying: “That’s the nice thing about her, she’s been developing with each race, so she seems to be getting better and better. That race in the Ashland was huge. She beat some nice fillies that day, and she did it all on her own terms.” – Jockey Brian Hernandez, Jr.

PP. 12 Dorth Vader (Dark Bay Filly)

• Sire: Girvin
• Dam: Hardcore Candy, by Yonaguska
• Trainer: Michael Yates
• Owner: John Ropes
• Jockey: Luis Saez
• Record and earnings: 8-4-0-1, $$339,633
• Morning Line Odds: 20-1
• Last Race: Fourth in Grade 2 Gulfstream Park Oaks
• Why You Should Bet Her: Upset the field at odds of 46-1 to take the Grade 2 Davona Dale Stakes at Gulfstream Park on March 4 by 4 3/4 lengths.
• Why You Should Save Your Money: Has yet to win beyond a mile or around two turns and was a well-beaten fourth when stretching out to 1 1/16 miles in the Gulfstream Park Oaks.
• What They’re Saying: “The first time going two turns, she made the lead really easy and I think it kind of surprised her seeing a horse come back outside her. She kind of cocked her head and drifted in and switched leads real late. She just ran a little bit green.” – Trainer Michael Yates.

PP. 13 Affirmative Lady (Gray Filly)

• Sire: Arrogate
• Dam: Stiffed, by Stephen Got Even
• Trainer: Graham Motion 
• Owner: AMO Racing USA
• Jockey: John Velazquez 
• Record and earnings: 6-2-1-2, $270,568
• Morning Line Odds: 10-1
• Last Race: Won Grade 2 Gulfstream Park Oaks by two lengths
• Why You Should Bet Her: Is getting good at just the right time after taking five tries to win her first race. Following her maiden win at Gulfstream Park on Feb. 26, she shook off being bumped at the start to close strongly down the lane in the Gulfstream Park Oaks. Should handle the Kentucky Oaks’ 1 1/8-mile distance with no issue if her pedigree is any indication. 
• Why You Should Save Your Money: Both of her career wins have come at Gulfstream Park so there is some question about how her form translates outside of Florida.
• What They’re Saying: “I feel like she belongs in the Oaks, and I think for her the (1 1/8-miles) distance is really going to help her. Honestly, I wish it were a mile and a quarter because I think the further she goes the better. I think we belong to be in there.” – Trainer Graham Motion.

PP. 14 Pretty Mischievous (Bay Filly)

• Sire: Into Mischief
• Dam: Pretty City Dancer, by Tapit
• Trainer: Brendan Walsh
• Owner: Godolphin
• Jockey: Tyler Gaffalione 
• Record and earnings: 6-4-1-1, $501,310
• Morning Line Odds: 10-1
• Last Race: Second in Grade 2 Fair Grounds Oaks 
• Why You Should Bet Her: Has shown solid progression since running third in the Grade 2 Golden Rod Stakes at Churchill Downs last November — a race where she finished ahead of eventual Grade 1 winner Defining Purpose. Won the Untapable Stakes by 3 1/4 lengths over fellow Oaks entrant The Alys Look at Fair Grounds in December and took the Grade 2 Rachel Alexandra Stakes by three-quarters of a length before running second in the Fair Grounds Oaks. Sports a 2-for-3 record at Churchill Downs.
• Why You Should Save Your Money: Southlawn defeated Pretty Mischievous pretty soundly in the Fair Grounds Oaks, which may have been a product of the latter moving a bit too soon that day.
• What They’re Saying: “She likes this track (Churchill Downs). She won her first two races here at Churchill Downs, and she ran third in the Golden Rod. Everything seems to be going smoothly enough. If we get a good week then we’ll be all set.” – Trainer Brendan Walsh.