The Kentucky Derby (and the Kentucky Oaks) is right around the corner, which means it's time for detailed looks at the horses that could fill the starting gate with Andrew Champagne of Catena Media and The Saratogian's Pink Sheet.
Check back with the Paulick Report regularly for updated rankings that include news, notes, and opinions on the 3-year-olds that figure to take center stage.
Most weeks, the Derby Bubble focuses on, well, the Kentucky Derby. However, this week, we'll look at the fillies and the 2023 Kentucky Oaks.
A field of 14 3-year-old females will line up on the first Friday in May. With just a week until that day, let's dive into the prospective field!
Kentucky-bred contenders will be highlighted in red, and will receive additional analysis into their breeders, broodmares, and auction histories. Pedigree notes are written by Joe Nevills.
#1: Wet Paint
Pedigree: Blame – Sky Painter (by Street Cry)
Owner: Godolphin
Trainer: Brad Cox
Breeder: Godolphin (KY)
Kentucky Oaks points: 170
We'll start in the most logical place, with the filly that's emerged as the probable Kentucky Oaks favorite. Wet Paint comes into the Oaks on a streak of three straight stakes wins at Oaklawn Park. Most recently, she rallied from last to first to win the G3 Fantasy. She's coming into form at the right time for a barn that wins races as well as any on the circuit, and that's impossible to ignore.
Wet Paint was homebred in Kentucky by Godolphin, out of the Grade 3-placed Street Cry mare Sky Painter, who is herself a Godolphin homebred. The operation of Sheikh Mohammed Al-Maktoum entered into the family through second dam Skylighter, a Grade 2 winner who joined the broodmare band during Godolphin's acquisition of Stonerside Stable and its equine assets.
#2: And Tell Me Nolies
Pedigree: Arrogate – Be Fair (by Exchange Rate)
Owner: Peter Redekop
Trainer: Peter Miller
Breeder: Lara Run LLC (KY)
Kentucky Oaks points: 70
It's weird putting a horse second when she hasn't won her last three starts. However, And Tell Me Nolies has been chasing the undefeated Faiza, who is ineligible for Kentucky Oaks points and would be no worse than this race's second choice. This filly, meanwhile, won a pair of graded stakes races as a 2-year-old. Toss out her clunker in the Breeders' Cup Juvenile Fillies, and assume Faiza doesn't exist (which, for the sake of the Kentucky Oaks, she doesn't), and her resume looks much, much better.
And Tell Me Nolies was bred in Kentucky by Lara Run LLC, out of the Grade 3-winning Exchange Rate mare Be Fair. She sold as a short yearling for $70,000 at the 2021 Keeneland January Horses of All Ages Sale, then she brought $230,000 at the Ocala Breeders' Sales Co. Spring Sale of 2-Year-Olds in Training. Lara Run acquired Be Fair, pregnant to Practical Joke, for $50,000 at the 2018 Keeneland November Breeding Stock Sale.
#3: Pretty Mischievous
Pedigree: Into Mischief – Pretty City Dancer (by Tapit)
Owner: Godolphin
Trainer: Brendan Walsh
Breeder: Godolphin (KY)
Kentucky Oaks points: 103
Pretty Mischievous has never run a bad race. In six career starts, she's notched four wins and hasn't been worse than third. Two of those victories came in stakes races, and she may have moved just a bit too soon in the G2 Fair Grounds Oaks. Furthermore, she's 2-for-3 at Churchill Downs, so you know she can handle this surface.
Pretty Mischievous is a Kentucky homebred for Godolphin, out of the Grade 1-winning Tapit mare Pretty City Dancer. Godolphin acquired the dam, pregnant to Medaglia d'Oro for $3.5 million at the 2018 Fasig-Tipton November Sale.
#4: Southlawn
Pedigree: Pioneerof the Nile – Mo d'Amour (by Uncle Mo)
Owner: Robert Masterson
Trainer: Norm Casse
Breeder: WinStar Farm (KY)
Kentucky Oaks points: 100
The question is, which Southlawn do you think shows up on the first Friday in May? If it's the Southlawn that's won two straight at Fair Grounds, including a handy score in the Fair Grounds Oaks, she's got a big shot. However, it's worth noting she's 0-for-2 over the main track at Churchill Downs, and she wasn't better than fifth either time. Perhaps she's matured since her 2-year-old campaign, though, and if she has, she's a threat.
Southlawn was bred in Kentucky by WinStar Farm, out of the Grade 2-placed Uncle Mo mare Mo d'Amour. Masterson bought Southlawn for $290,000 at the 2021 Keeneland September Yearling Sale.
#5: Defining Purpose
Pedigree: Cross Traffic – Defining Hope (by Strong Hope)
Owner: Magdalena Racing, Vanmatre, and Ball
Trainer: Ken McPeek
Breeder: Colette Marie VanMatre (KY)
Kentucky Oaks points: 107
Defining Purpose pulled off a 20-1 upset in the G1 Ashland, but perhaps that shouldn't have been such a surprise from a pari-mutuel standpoint. She'd misfired in the G3 Honeybee, but previously ran third in the Martha Washington behind Wet Paint after winning a minor stakes race. She may still have some ground to make up on the division leader, but it sure seems like she's moving the right way.
Defining Purpose was bred in Kentucky by Colette Marie VanMatre, out of the multiple stakes-winning Strong Hope mare Defining Hope, who was herself a homebred for VanMatre.
#6: The Alys Look
Pedigree: Connect – Foul Play (by Harlan's Holiday)
Owner: Ike and Dawn Thrash
Trainer: Brad Cox
Breeder: G. Watts Humphrey Jr. (KY)
Kentucky Oaks points: 54
If you throw out the October 2022 clunker where she had a nightmare trip, The Alys Look really hasn't done much wrong. She came onto the scene with a win in January's Silverbulletday, and she punched her ticket to the Kentucky Oaks with a third-place finish in the Fair Grounds Oaks. Cox has won this race twice, and between this one, Wet Paint, and another runner we'll talk about pretty soon, he's got every chance to walk away with a third bed of lilies.
The Alys Look was bred in Kentucky by G. Watts Humphrey Jr., out of the winning Harlan's Holiday mare Foul Play, who is herself a product of Humphrey's breeding program. This bloodline entered the Humphrey program through third dam Cyber Cat, who he acquired from his aunt, breeder Pamela Firman.
#7: Affirmative Lady
Pedigree: Arrogate – Stiffed (by Stephen Got Even)
Owner: AMO Racing USA
Trainer: Graham Motion
Breeder: Alastar Thoroughbred Co, LLC (KY)
Kentucky Oaks points: 110
Affirmative Lady sits second on the Oaks leaderboard after a mild 8-1 upset in the G2 Gulfstream Park Oaks. She was winless as a 2-year-old but danced some big dances, including when she ran second in the G2 Demoiselle at Aqueduct. She may need to improve again in order to contend with the divisional heavyweights, but given her distance-heavy pedigree, it's safe to assume the nine-furlong trip will be right in her wheelhouse.
Affirmative Lady was bred in Kentucky by Alastar Thoroughbred Co., out of the Grade 3-placed stakes-winning Stephen Got Even mare Stiffed. She was a $210,000 purchase at the 2021 Keeneland September sale. The breeder acquired Stiffed for $320,000, pregnant to Pioneerof the Nile, at the 2018 Keeneland November Sale.
#8: Botanical
Pedigree: Medaglia d'Oro – Daisy (by Blame)
Owner: LNJ Foxwoods and Clearsky Farms
Trainer: Brad Cox
Breeder: Clearsky Farms & Godolphin (KY)
Kentucky Oaks points: 70
When she was shipped to Turfway Park late last year, Botanical blossomed (yep, sometimes a writer just has to take the low-hanging fruit). She won a pair of stakes races in March, and one of those efforts was an easy wire-to-wire score in the Bourbonette Oaks. Of course, the big question is whether or not she can replicate that type of form on conventional dirt.
Botanical was bred in Kentucky by Clearsky Farms and Godolphin, out of the Grade 3-winning Blame mare Daisy. Botanical brought $220,000 at the 2021 Keeneland September sale.
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If you appreciate our work, you can support us by subscribing to our Patreon stream. Learn more.#9: Wonder Wheel
Pedigree: Into Mischief – Wonder Gal (by Tiz Wonderful)
Owner: D.J. Stable
Trainer: Mark Casse
Breeder: Three Chimneys Farm, LLC & Clearsky Farms (KY)
Kentucky Oaks points: 48
What do we do with last year's champion 2-year-old filly? Wonder Wheel won two Grade 1 races last year and was second in another. This season, she just hasn't been the same horse. Her loss in the Suncoast was surprising. Her clunker in the Ashland was shocking. If Casse can orchestrate a return to her 2-year-old form, Wonder Wheel could have every chance…but as a handicapper, just how forgiving do you want to be?
Wonder Wheel was bred in Kentucky by Three Chimneys Farm and Clearsky Farms, out of the Grade 1-placed stakes-winning Tiz Wonderful mare Wonder Gal. D.J. Stable purchased Wonder Wheel for $275,000 at the 2021 Keeneland September sale.
#10: Promiseher America
Pedigree: American Pharoah – Promisedyouheaven (by Unbridled's Song)
Owner: Hoffman Thoroughbreds and Tom McCrocklin
Trainer: Ray Handal
Breeder: Robert Low & Lawana Low (KY)
Kentucky Oaks points: 100
The G3 Gazelle wasn't seen as one of the premier Oaks preps of the season, but Promiseher America shook up the standings with a 26-1 upset. She raced just once as a 2-year-old and was eligible for a first-level allowance at the time of her Gazelle shocker, but rather than be conservative, the Handal barn took a shot, and it paid off. It's likely, however, that she'll need another significant step forward next week.
Promiseher America was bred in Kentucky by Robert and Lawana Low, out of the winning Unbridled's Song mare Promisedyouheaven. The filly brought $75,000 at the 2022 OBS Spring Sale. The Lows bought Promisedyouheaven with Promiseher America in-utero for $370,000 at the 2019 Fasig-Tipton November Sale.
#11: Dorth Vader
Pedigree: Girvin – Hardcore Candy (by Yonaguska)
Owner: John Ropes
Trainer: Michael Yates
Breeder: John Ropes (FL)
Kentucky Oaks points: 70
Dorth Vader blew up the tote board by winning the G2 Davona Dale at odds of 46-1 back in March. She followed that up, though, with a distant fourth behind Affirmative Lady in the Gulfstream Park Oaks. A look at her form tells a story: She's won three stakes races going one turn, but is unproven at two-turn routes.
#12: Gambling Girl
Pedigree: Dialed In – Tulipmania (by Empire Maker)
Owner: Repole Stable
Trainer: Todd Pletcher
Breeder: Gallagher's Stud (NY)
Kentucky Oaks points: 61
One of the more battle-tested horses on the Oaks trail, Gambling Girl has already raced nine times. She's won just twice, but her record includes four placings in Kentucky Oaks preps, including a second behind Promiseher America in the Gazelle. Pletcher's Hall of Fame career includes four wins in this race, most recently with Malathaat in 2021.
#13: Flying Connection
Pedigree: Nyquist – Free Flying Soul (by Quiet American)
Owner: King, Andrews, Coleman, Cone et al
Trainer: Todd Fincher
Breeder: Liberty Road Stables (KY)
Kentucky Oaks points: 50
Flying Connection wintered in New Mexico and has developed into a horse with ample early speed. That was a weapon in the Sunland Park Oaks, where she went wire-to-wire and locked up a third career stakes win. The waters are much, much deeper here, but at a minimum, one has to think she's a pace factor.
Flying Connection was bred in Kentucky by Liberty Road Stables, out of the Grade 1-placed stakes-winning Quiet American mare Free Flying Soul. The ownership group bought Flying Connection for $250,000 at the 2021 Keeneland September sale. Free Flying Soul was purchased by Marsha Naify of Liberty Road Stables for $125,000 at the 2007 Barretts May 2-Year-Olds in Training Sale.
#14: Mimi Kakushi
Pedigree: City of Light – Rite Moment (by Vicar)
Owner: Sheikh Hamdan bin Mohammed Al Maktoum
Trainer: Salem Bin Ghadayer
Breeder: Woodford Thoroughbreds, LLC (KY)
Kentucky Oaks points: 50
We'll finish off this list with the shipper from Dubai. Mimi Kakushi has won three in a row, including the G3 UAE Oaks. She hasn't run since that February effort, though, and while the winner of the Kentucky Derby prep at Meydan is getting plenty of steam, it wouldn't be a shock if this one was one of the longer shots on the board in the Derby's sister race.
Mimi Kakushi was bred in Kentucky by Woodford Thoroughbreds, out of the multiple Grade 2-winning Vicar mare Rite Moment. The filly sold as a yearling for $180,000 at the 2021 Fasig-Tipton July Sale, then she brought $250,000 the following year at the Fasig-Tipton Midlantic 2-Year-Olds in Training Sale. Woodford Thoroughbreds bought Rite Moment, pregnant to Smart Strike, for $400,000 at the 2010 Keeneland November sale.
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