The $1.25 million, Grade 1 Longines Kentucky Oaks at Churchill Downs dates back to 1875. The 1 1/8-mile race for 3-year-old fillies is as old as the coveted Grade 1 Kentucky Derby Presented by Woodford Reserve and boasts an elite roster of winners.
The recent history of the Oaks has been particularly compelling. Champion 3-year-old fillies Bird Town (2003), Ashado (2004), Rags to Riches (2007), Proud Spell (2008), Rachel Alexandra (2009), Blind Luck (2010), Untapable (2014), Abel Tasman (2017), Monomoy Girl (2018), and Malathaat (2021) have all won the Oaks during the last two decades. In 2020, Shedaresthedevil beat a strong field in the record time of 1:48.28. And last year, Secret Oath defeated champion Nest to give Hall of Fame trainer D. Wayne Lukas a record-equaling fifth Kentucky Oaks victory.
The 2023 Kentucky Oaks is shaping up to be another memorable renewal. There aren’t any obvious standout superstars on paper, so the race has drawn an overflow field of 17 entries, with a maximum of 14 allowed to participate. A case can be made for many of the fillies entered to visit the winner’s circle. That said, the morning-line favorite and second choice bring impressive credentials to the table.
We’ll start our analysis with #7 Wet Paint (5-2), a Godolphin homebred conditioned by two-time Kentucky Oaks-winning trainer Brad Cox. Wet Paint is undefeated in four starts on dirt, including three consecutive victories in the Martha Washington Stakes, Grade 3 Honeybee Stakes, and Grade 3 Fantasy Stakes on the road to the Kentucky Oaks.
It’s hard to knock anything Wet Paint has accomplished. Her three stakes wins have come by a minimum of two lengths, and she’s defeated talented fillies like Grade 1 Central Bank Ashland Stakes winner #11 Defining Purpose (12-1) and Grade 3 Gazelle Stakes runner-up #3 Gambling Girl (15-1). The one concern is Wet Paint’s lack of tactical speed; she’s a deep closer who rallies from far behind, and there’s no guarantee she’ll receive a traffic-free trip Friday against a large field.
There should be no such concerns for Wet Paint’s Cox-trained stablemate #6 Botanical (4-1). Early speed is the name of the game for Botanical, who enters off a gate-to-wire victory in the Bourbonette Oaks at Turfway Park. But lest anyone worry about Botanical being a one-dimensional pacesetter, she demonstrated in the Cincinnati Trophy Stakes two starts back that she can rate behind the leaders if necessary. In the Cincinnati Trophy, Botanical relaxed as many as nine lengths behind a runaway pacesetter before sweeping past to dominate by 6 1/2 lengths.
The question mark for Botanical is racing on dirt. She’s never competed on the surface, and all four of her victories have come on the synthetic Tapeta Footings surface at Turfway Park. But Botanical’s pedigree suggests the switch to dirt won’t be an issue; sire Medaglia d’Oro won three Grade 1 races on dirt, dam Daisy nabbed the Grade 3 Tempted Stakes on dirt, and broodmare sire Blame was voted champion older male after winning the Grade 1 Breeders’ Cup Classic and two other Grade 1 races on dirt.
The third choice on the Kentucky Oaks morning line is #4 Southlawn (8-1), who has impressively won two starts since undergoing surgery to correct a breathing issue. She kicked off 2023 in an allowance-optional claiming race at Fair Grounds, making an early move from 2 1/2 lengths off the pace to crush her competition by eight lengths. Then she stepped up in class for the Grade 2 Fair Grounds Oaks Presented by Fasig-Tipton and defeated road to the Kentucky Oaks stakes winners #14 Pretty Mischievous (10-1), #2 The Alys Look (15-1), and #17 Hoosier Philly (30-1) by 3 1/4 lengths.
The Fair Grounds Oaks has produced half a dozen Kentucky Oaks winners since 2005, so it’s safe to call it a pivotal prep race. Southlawn is clearly much better this year than last year, and she enters the Kentucky Oaks off a fast series of workouts at Churchill Downs, so a top-three finish is well within reach for this improving filly.
Beyond the three favorites, the above-mentioned Pretty Mischievous warrants respect after finishing second in the Fair Grounds Oaks. She’s previously won the Grade 2 Rachel Alexandra Stakes Presented by Fasig-Tipton with a pace-tracking trip, and last year she won two of her three starts at Churchill Downs. There’s a lot to like about this Godolphin homebred.
#11 Defining Purpose (12-1) can’t be counted out of the mix either. Third in the Martha Washington and sixth in the Honeybee, Defining Purpose improved in her final prep for the Kentucky Oaks, tracking the pace in the Grade 1 Central Bank Ashland Stakes at Keeneland before battling on to win by half a length. It’s worth noting four of the last eight Kentucky Oaks winners contested the Ashland on their way to Churchill Downs.
So how can we take all of these opinions and turn them into a Kentucky Oaks betting strategy? Depending on your budget, we’ll bet either Wet Paint and Botanical on top of an exacta adding Southlawn for second place, or we’ll play that exacta and add trifectas incorporating Pretty Mischievous and Defining Purpose into the mix for third place.
Wagering Strategy on a $12 Budget
$3 exacta: 6,7 with 4,6,7 ($12)
What to say at the betting window: Churchill Downs, Race 11, $3 exacta 6,7 with 4,6,7
Wagering Strategy on a $24 Budget
$6 exacta: 6,7 with 4,6,7 ($24)
What to say at the betting window: Churchill Downs, Race 11, $6 exacta 6,7 with 4,6,7
Wagering Strategy on a $48 Budget
$6 exacta: 6,7 with 4,6,7 ($24)
What to say at the betting window: Churchill Downs, Race 11, $6 exacta 6,7 with 4,6,7
$3 trifecta: 6,7 with 4,6,7 with 4,6,7 ($12)
What to say at the betting window: Churchill Downs, Race 11, $3 trifecta 6,7 with 4,6,7 with 4,6,7
$1.50 trifecta: 6,7 with 4,6,7 with 11,14 ($12)
What to say at the betting window: Churchill Downs, Race 11, $1.50 trifecta 6,7 with 4,6,7 with 11,14
Good luck, and enjoy the race!
Pick 3
1-8-14
1-8-14
$341
Pick 4
10/11/12-1-8-14
10/11/12-1-8-14
$544
Pick 5
6-10/11/12-1-8-14
6-10/11/12-1-8-14
$7,169
Pick 6 Jackpot
2-6-10/11/12-1-8-14
2-6-10/11/12-1-8-14
$16,942
Daily Double
8-14
8-14
$165
Future Wager
POOL 1 - 29
POOL 1 - 29
$33
Future Wager
POOL 1 EXACTA 29-16
POOL 1 EXACTA 29-16
$8,772
Superfecta
14-3-2-7
14-3-2-7
$15,391
Super High Five
14-3-2-7-12
14-3-2-7-12
$111,346
Trifecta
14-3-2
14-3-2
$1,997
Pick 3
1-8-14
1-8-14
$341
Pick 4
10/11/12-1-8-14
10/11/12-1-8-14
$544
Pick 5
6-10/11/12-1-8-14
6-10/11/12-1-8-14
$7,169
Pick 6 Jackpot
2-6-10/11/12-1-8-14
2-6-10/11/12-1-8-14
$16,942
Daily Double
8-14
8-14
$165
Future Wager
POOL 1 - 29
POOL 1 - 29
$33
Future Wager
POOL 1 EXACTA 29-16
POOL 1 EXACTA 29-16
$8,772
Superfecta
14-3-2-7
14-3-2-7
$15,391
Super High Five
14-3-2-7-12
14-3-2-7-12
$111,346
Trifecta
14-3-2
14-3-2
$1,997
