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Kentucky Oaks Longshot Watch

Writer's picture: Chelsea Lowman Chelsea Lowman

Positive Spirit, photo by Leila Elliot/Bits and Pieces

The 145th running of the Kentucky Oaks is days away. The multiple graded stakes winning phenom, Bellafina, looks poised to add the Grade 1 event to her collection of victories, and end the day draped in lilies. With six trips to the winner's circle from eight starts and career earnings of $1,068,000, it is no wonder that Bellafina has been installed as the 2-1 morning line favorite for the 1 1/8-mile test. Currently undefeated in 2019, there isn't much not to like about this striking filly as the race draws closer. However, with her low odds there isn't much money to be made when betting this horse in the Kentucky Oaks.


It's no secret that the value lies within the longshots, and there are quite a few entering this race that do not deserve to be counted out entirely. Whether these horses are used in your wagers underneath Bellafina, or are used on top with the possibility of an upset, these underdogs deserve another look. Here are four Kentucky Oaks underdogs that have the potential to add value to your wagers:


Positive Spirit

Positive Spirit is a sneaky-good longshot that is entering the Kentucky Oaks with a race record that is better than many give her credit for. Kicking off her career at the age of two for owners Mike Ryan and Gerry Dilger, Positive Spirit finished third in her debut at Aqueduct Racetrack, but improved to finish a solid second in her next start. The third time proved to be the charm for the Rodolphe Brisset trainee, when she cruised to victory in a one-mile maiden special weight at Churchill Downs.


Positive Spirit stepped up her game in her next start when she entered the $250,000 Demoiselle Stakes (G2) at Aqueduct Racetrack. It was a huge step-up in class for the bay filly, but Positive Spirit quickly proved that she could more than hold her own against a higher level of competition. After stalking the pace for most of the race, Positive Spirit drew even with rivals Enliven and Filly Joel, engaging in a three-horse battle around the final turn. Digging in fiercely, Positive Spirit found more and lunged forward with breathtaking acceleration. In a trice, the fleet-footed filly was in the clear, waltzing away from her battered rivals as if they were standing still. With Manuel Franco in the saddle, Positive Spirit thundered to victory by a crushing 10 1/2 lengths. The final time for the 1 1/8-mile test came in 1:56.01.


Positive Spirit returned to the races in February, making her three-year-old debut in the Rachel Alexandra Stakes (G2). The filly proved to be a shadow of her previous performance, and failed to fire in the event. After being restless in the gate and racing wide throughout the race, Positive Spirit finished a shocking eighth. It was simply not the filly's day.



Positive Spirit rebounded from her uncharacteristically poor performance in the Rachel Alexandra Stakes and returned with an admirable effort in the Gazelle Stakes (G2). Positive Spirit boldly set the pace in the 1 1/8-mile race. Ambushed by a frenzied mob of horses in the stretch, Positive Spirit stubbornly pressed on. In a gritty display of heart and courage, the nimble filly flew down the stretch, reaching for the finish line in a desperate attempt to wire the race. However, it was not meant to be. Always Shopping, winner of the Busanda Stakes, came sweeping up to steal the show. Unwilling to give in completely, Positive Spirit stormed forward, successfully fending off the rest of her challenges to finish second. Positive Spirit tasted defeated by less than two lengths.


Positive Spirit has been training very forwardly leading up to the Kentucky Oaks. Her final workout for the $1.25 million event came in the form of a bullet, when she scorched through four-furlongs in a sharp final time of :47.20. Of the 33 horses that worked the same distance on that day, Positive Spirit's time was unmatched.


Positive Spirit not only comes into the Kentucky Oaks with a decent race record, but also enters the race with a pedigree of riches. Positive Spirit is by the late, great Pioneerof the Nile, who is famous for siring 2015 Triple Crown champion, American Pharoah. The dam of Positive Spirit, Above Perfection, is also well known. Above Perfection is the mare responsible for producing multiple graded stakes winner, Hot Dixie Chick, as well as 2017 Kentucky Derby hero, Always Dreaming.


Wouldn't it be something if Positive Spirit could follow in her brother's hoof prints and rise to glory beneath the Twin Spires? Installed as a 30-1 longshot, the odds are certainly not in her favor to do so. However, in horse racing, anything is possible. Positive Spirit is proven at the 1 1/8-mile distance of the race, already has a win over the strip of Churchill Downs, and is coming into the race in excellent form. The filly appears to be improving at just the right time, and has a real possibility at outrunning her odds on Friday. Win or lose, Positive Spirit is a filly that you might want to include on your tickets.


Lady Apple

Handed with morning line odds of 20-1, Lady Apple is yet another longshot that is better than her lofty odds suggest. Owned by Pheonix Thoroughbreds and KatieRich Stables, and trained by Steve Asmussen, Lady Apple's career began at the age of two, when she finished second in a maiden special weight at Keeneland Racecourse. Despite her loss, her connections felt confident enough to enter her in the Astoria Stakes in what was only her second start. The bay filly rewarded her connections with yet another solid effort, finishing second in the 5 1/2 furlong test. Lady Apple was then sent to compete in the Schuylerville Stakes (G3), where she could do no better than fifth.


After Lady Apple's disappointing finish in the Schuylerville Stakes, she returned to easier competition in a maiden special weight race at Saratoga. Once again, the filly finished fifth. Lady Apple was given the rest of the season off after her sub-par effort.


Lady Apple returned to action in a maiden special weight as a three-year-old, finally making that coveted trip to the winner's circle in her first start back. She then claimed victory in an allowance race before moving on to stiffer competition in the Fantasy Stakes (G3).


Dismissed and sent off with odds of 9-1, Lady Apple sat off the pace in the Fantasy Stakes, waiting for the perfect moment to strike. When jockey Ricardo Santana Jr. asked Lady Apple to go, she took off like a rocket. Extending her powerful stride, Lady Apple swiftly propelled herself over the ground, kicking past one rival after the other. In a bold and daring move, the unflappable bay squeezed through an opening on the rail and blew past the leaders in the final stages of the 1 1/16-mile test. Lady Apple stopped the clock in a final time of 1:43.88, one-length ahead of her nearest rival.


Lady Apple is on a roll in 2019, having yet to meet a filly who can best her. While the competition for the Kentucky Oaks will be the deepest and most talented field this filly has ever faced, she is coming into the event in perfect form. She has been training very well as she approaches the biggest race of her life, and has a pedigree that can only help her case.


Lady Apple is by two-time Horse of the Year, Curlin, and is out of a graded stakes placed mare, Miss Mary Apples. Her pedigree alone suggests that the 1 1/8-mile distance of the Kentucky Oaks shouldn't be a problem, and with so many quick horses in the race, Lady Apple should have plenty of speed to track.


Chocolate Kisses

Chocolate Kisses is an interesting filly in this year's edition of the Kentucky Oaks. Her record isn't quite as flashy as some of the other longshot fillies mentioned in this article, but she has the potential to run big when she wants to, and a running style that fits in perfectly with this race. With juicy morning line odds of 20-1, you just might want to give her a closer look.



Owned by Debby Oxley and trained by Mark Casse, Chocolate Kisses started her career at the age of two, finishing second in her debut. The bay daughter of Candy Ride scored in her next try on the turf, but then had to settle for third when she stepped up in class in the P.G. Johnson Stakes. She faltered once again in her next start, finishing no better than fourth in the Darley Alcibiadies Stakes (G1).


Chocolate Kisses made her final start of 2018 in the Rags to Riches Stakes at Churchill Downs. Luck was not on the filly's side that day, as she jumped at the start and unseated her rider.


Chocolate Kisses was more fortunate upon her return to the track as a three-year-old, scoring in an allowance optional claiming event on the turf in her seasonal debut. Chocolate Kisses then returned to dirt, sweeping to victory in the $200,000 Honeybee Stakes (G3). With a sublime turn of foot, Chocolate Kisses ran down her competition to score by one-length in the 1 1/16-mile journey, stopping the clock in 1:45.78.


Chocolate Kisses failed to rally in her final prep for the Kentucky Oaks, when she finished sixth in the Ashland Stakes (G1). While the disappointing finish makes it difficult to trust her moving forward, it is hard to count her out entirely when looking at the likely pace scenario for the Kentucky Oaks. The race is loaded with front-running horses, which means that the pace for the Kentucky Oaks is likely to be a hot one. A deep closer, Chocolate Kisses should have plenty of speed to run down, giving her the perfect set-up for her running style. This filly might be one you want to use in your exotics, as she will be passing tired horses in the stretch.


Restless Rider

With morning line odds of 6-1, Restless Rider is not among some of the greater misfits in the Kentucky Oaks. However, this talented filly is still capable of adding some value to your wagers.


Owned by Fern Circle Stables and Three Chimney Farm, Restless Rider is trained by Ken McPeek and ridden by Brian Hernandez Jr. The gray or roan filly began her career with a victory at the age of two, and followed it up with yet another score when she sailed to victory in the Debutante Stakes at Churchill Downs. She then finished a solid second in the Spinaway Stakes (G1), but bounced back to take down the Darley Alcibiades (G1) one month later. Her season ended with a pair of runner-up efforts in the Breeders' Cup Juvenile Fillies (G1) and the Golden Rod Stakes (G2), respectively.


Restless Rider had a late start to her three-year-old season, but returned in time to secure a spot in the Kentucky Oaks. Her lone race of 2019 came in the Ashland Stakes (G1), where she finished a very game second to 52-1 longshot, Out for a Spin. It was an impressive effort after a five-month layoff, and it appears as if Restless Rider is primed to improve moving forward.


With a solid race under her belt, Restless Rider appears ready to fire a strong effort in the Kentucky Oaks. She has been training beautifully for the upcoming race, and holds somewhat of an advantage over her competition, having already competed over the course of Churchill Downs four times, with half of those efforts resulting in trips to the winner's circle.


Familiar with the battlegrounds and likely to improve, this plucky daughter of Distorted Humor has a very live chance of having a say in the outcome of the Kentucky Oaks. Her biggest challenge coming into the event is the fact that she drew the dreaded 14 post, which could make things tricky. However, this filly is coming into this race at just the right time, and with a record that shows her never finishing worse than second, there isn't much not to like about this filly.


Restless Rider, photo by Leila Elliot/Bits and Pieces

Thank you to Leila Elliot for providing the lovely pictures!


Be sure to follow me on Twitter for more stories! https://twitter.com/Down2TheWire_



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