The Kentucky Derby is filled with mystery. When twenty of the world's most elite three-year-old thoroughbreds come together beneath the iconic Twin Spires, there's no telling what is going to happen. With so many talented horses in one race, it is a true mystery as to who will prevail and wear the coveted cape of roses. Part of the lure of the Kentucky Derby is not only trying to figure out who will come out on top, but also trying to solve the puzzle of who to include in your wagers underneath the suspected winner.
History has witnessed massive payouts when it comes to winning Kentucky Derby trifectas and superfectas. It is not uncommon for horses with lofty odds to jump up and hit the board in the Kentucky Derby, rewarding their backers handsomely with their added value. In this year's edition of the Kentucky Derby, there is one sneaky longshot in particular that comes to mind that you do not want to leave off of your tickets.
Win Win Win
Win Win Win is a talented yet overlooked horse coming in to this year's edition of the Kentucky Derby. With only one trip to the winner's circle in 2019, it is easy to understand why there isn't a lot of buzz surrounding this horse. However, his efforts on the track have been better than they appear, and it's not impossible to think that this horse could have a say in the finish of the race.
Win Win Win began his career at the age of two at Laurel Park. The Michael Trombetta trainee kicked off his career with two wins in a row before finishing second in the Heft Stakes in his third start. The colt then returned to the winner's circle upon his debut as a newly turned three-year-old, winning the Pasco Stakes at Tampa Bay Downs in style. With jockey Julian Pimentel in the irons, Win Win Win blazed through the seven-furlong test in track record time, stopping the clock in a swift 1:20.89.
Win Win Win stepped things up in his next start, taking on fiercer competition in the Grade 2 Lambholm South Tampa Bay Derby. Irad Ortiz Jr. was given the mount in place of Win Win Win's regular rider, and the new duo could do no better than third in the $400,000 event. Victory went to the highly talented and regally-bred, Tacitus. Yet, Win Win Win lost little in defeat. He was closing in on the leaders with the frenzied acceleration of a freight train that day, falling short just at the wire. The gritty colt finished with a lot of fight left inside of him, and appeared more than ready to try again.
Win Win Win ventured to Keeneland Racecourse to compete in the Toyota Bluegrass Stakes (G2). It was the colt's final prep for the Kentucky Derby, and while he fell short once again, he still put forth an admirable effort. As game and determined as ever, Win Win Win soared past all but one rival in the stretch. The victorious Vekoma was home free, but Win Win Win's runner-up effort was still enough to earn him a spot in the Kentucky Derby.
Win Win Win has been training phenomenally in the wake of his second place finish in the Bluegrass. He has posted two solid workouts since the $1 million event, with his latest work taking place on April 28, at Churchill Downs. The dark son of Hat Trick was out for a four-furlong drill with workmate, Souper Courage, when he hooked up with not one, but two other horses. With his unyielding competitive nature shining through, Win Win Win rolled up to confront fellow Derby contenders Tacitus and Country House after leaving his workmate behind. Unwilling to settle behind his rivals, Win Win Win confidently galloped ahead of his targets in a brazen display of heart and tenacity, completing his work in a sharp :47.60. Of the 76 horses that worked the same distance that day, Win Win Win's breeze was the fourth-fastest.
Win Win Win's breeze was followed up with a powerful gallop out, with Win Win Win showing all the signs that he is loaded with strength and energy as he prepares to enter the biggest race of his young life.
Win Win Win has a lot going for him as the Kentucky Derby draws near. For starters, Win Win Win will be reunited with his regular rider, Pimentel for the "Run for the Roses". It also helps that the colt is entering the race off of a strong performance in his final prep, boasting a record that shows that he has never finished worse than third in his six-race career. It should also be noted that Win Win Win descends from a family tree that is rich in Kentucky Derby history. He is by Hat Trick, who himself was sired by 1989 Kentucky Derby (and Preakness) hero, Sunday Silence. Win Win Win also has close relations to Kentucky Derby legends through his dam, Miss Smarty Pants, who is by 2004 Kentucky Derby (and Preakness) champion, Smarty Jones.
There is some question as to whether or not Win Win Win can handle the taxing 1 1/4 mile distance of the Kentucky Derby, but with the blood of past Kentucky Derby winners coursing through his veins, it's not far-fetched to think that this dauntless colt will be there fighting in the end. Win Win Win has already proven to be tough, determined, and fearless. He has never failed to rise to the challenge, and possesses a fierce competitive nature that is impossible to deny. Win or lose, there is a very strong chance that Win Win Win will be there in the stretch of the Kentucky Derby, giving his all.
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Thank you to Eric Kalet for providing the picture! You can find more of his work here: https://erickalet.zenfolio.com/
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