2025 Kentucky Oaks: Two Massive Longshots Who Could Shock The Field

Beating undefeated 6/5 morning-line favorite Good Cheer will not be an easy task for 13 rival fillies in the 2025 Kentucky Oaks.

After handicapping all 14 entrants, two fillies profile as potential moonshots who could crash the tote board in the latest installment of the "Lilies for the Fillies.”

No. 2 Simply Joking (30-1)

JOCKEY: Florent Geroux / TRAINER: Whit Beckman

RECORD: 3 starts: 2-1-0

TOP EQUIBASE SPEED FIGURE: 98

RUNNING STYLE: Stalker (prefers to press the pace)

CAREER EARNINGS: $288,000

Overlooking Simply Joking in the Oaks, solely due to limited racing experience (only three career starts), would be a big mistake. The daughter of Practical Joke finished just three-quarters of a length behind Oaks rival Quietside in the Grade 2 Fantasy Stakes. That narrow loss is all that kept her from starting her career with a perfect 3-for-3 record in stakes races. Let that sink in.

After impressively breaking her maiden, winning the $100,000 Letellier Memorial Stakes at the end of December at Fair Grounds, she returned to the winner’s circle after beating Oaks rivals Bless the Broken and Drexel Hill in the $150,000 Fasig-Tipton Silverbulletday Stakes to kick off her 2025 campaign.

👏 The team at @Ballysaxsales wishes SIMPLY JOKING and her connections the best of racing luck in the GI Kentucky Oaks!

Ballysax Manor raised & prepped. pic.twitter.com/c3ezp8gmQ4
— TDN (@theTDN) April 30, 2025

Simply Joking has been quietly firing bullets since arriving at Churchill Downs, working five-furlongs in :58:40 on April 19 followed by four-furlongs in :47:60 on April 25. Those morning works have Beckman confident in his lightly raced filly. “She has a lot of guts and a lot of resilience,” he said.

The talented gal has improved her Equibase Speed figures in each of her three starts (93-94-98) and that is the kind of trajectory you look for when betting on a longshot. If she takes another step forward, she is a serious contender, who could easily outrun her massive 30-1 morning-line odds.

Post Positions for the 151st Longines Kentucky Oaks. pic.twitter.com/K38MylPbn0
— Kentucky Derby (@KentuckyDerby) April 27, 2025

No. 13 Bless the Broken (30-1)

JOCKEY: John Velazquez / TRAINER: William Walden

RECORD: 7 starts: 2-2-1

TOP EQUIBASE SPEED FIGURE: 101

RUNNING STYLE: Closer

CAREER EARNINGS: $282,835

If the Oaks experiences a pace meltdown from a plethora of contenders battling fast on the front-end, it could set up for a closer to steal it late. Among the closers capable of capitalizing is the talented daughter of Laoban, who enters the Oaks fresh off a 2 ¾-length victory in the $300,000 Bourbonette Oaks at Turfway Park. She earned a career-best 101 Equibase Speed Figure in that effort.

🏆 BLESS THE BROKEN
(John Velazquez - William Walden)
BOURBONETTE OAKS 2025 ($300,000) Turfway Park @TurfwayPark @ljlmvel @wwaldenracing @MadaketStables @KPMRacingStable
📷 Coady Media pic.twitter.com/NQbjlpTgU7
— Stakes Winners 🏆 (@StakesWinners) March 26, 2025

Since her first stakes victory, Bless the Broken has turned in two impressive four-furlong works: :48.00 on April 23 and :47.80 on April 9 at Keeneland. If she is able to continue her progression and take another step forward in her fourth start of 2025, veteran jockey John Velazquez could earn an in-the-money finish at healthy moonshot odds.

Odds refresh periodically and are subject to change.

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