Win Win Win Horse: Meet the Jockey, Owner & Trainer

Win Win Win horse jockey owner trainer pedigree

Getty 2019 Kentucky Derby horse Win Win Win

Among the many intriguing horses with a talented jockey, owner and trainer working with them at the 2019 Kentucky Derby, Win Win Win is a name to watch. Win Win Win’s dam is Hat Trick and his sire is Miss Smarty Pants, per Horse Racing Nation, while the horse has a strong group which has led the way to a Kentucky Derby appearance.

Although his pedigree may not be as prestigious as some of the other horses in the race, the odds on Win Win Win to wind up victorious at this year’s Kentucky Derby have moved as high as 14/1 at points. We’re going to take a look at who’ll be leading the three-year-old colt who’s had success through the early stages of his career.

Among the four most recent performances, Win Win Win has posted two second-place finishes, one third and one victory. His win came back on January 19 at the Pasco Stakes at Tampa Bay Downs by 7 1/4 lengths, per the Kentucky Derby’s official website. Let’s meet the jockey, owner and trainer for Win Win Win.


Win Win Win’s Jockey: Julian Pimentel

Win Win Win horse jockey

GettyJockey Julian Pimentel

The situation with Julian Pimentel and Win Win Win is an interesting one, as he previously called the horse “one of the best he’s ever ridden,” per the Paulick Report. But after riding the horse to three wins and one second-place finish, it was Irad Ortiz Jr. who was the jockey during the Kentucky Derby-clinching two-race stretch.

While Pimentel lost his job previously, Ortiz chose to ride Improbable for the Kentucky Derby, leading to trainer Mike Trombetta calling him to potentially return for Saturday’s race.

“He called me and asked if I wanted to ride the horse back. I said, ‘I’ll have to see if I have any plans for that day,’” Pimentel joked. “No, I told him yes right away.”

This is Pimentel’s first run at the Kentucky Derby, but he’s had plenty of success over the 10,445 starts he’s made, as America’s Best Racing detailed. Over that stretch, Pimentel has won 1,664 races and racked up a total of $52,214,540 in career earnings.


Win Win Win’s Owner: Live Oak Plantation

The Live Oak Plantation has found plenty of success over the years behind owner Charlotte C. Weber. She is the granddaughter of Campbell Soup founder John T. Dorrance and is currently on the board of trustees for the company.

Over her time as the owner of the Live Oak Plantation, there have been a number of impressive finishes and performances by various horses, which America’s Best Racing detailed.

Top horses campaigned by Live Oak Plantation include Breeders’ Cup Mile winner and champion turf horse Miesque’s Approval and such Grade 1 winners as My Typhoon, To Honor and Serve and Zo Impressive. Live Oak earned a second Breeders’ Cup win in 2017 when World Approval won the Mile by 1 1/4 lengths. World Approval is a half-brother to Weber’s other Mile winner, Miesque’s Approval.

The Live Oak Plantation has surpassed $49.359 million in lifetime earnings while winning 16 percent of the races run during the 2019 season. Of the 4,152 starts made by their horses in history, it’s resulted in 793 wins, 672 second-place finishes and 556 third-place results.


Win Win Win’s Trainer: Michael J. Trombetta

As for Win Win Win’s trainer prior to the Kentucky Derby, it was Michael J. Trombetta who’s helped guide the horse. He’s had plenty of success throughout his career as a trainer, and as Equibase shows, Trombetta worked with Sweetnorthernsaint during his second-place finish at the 2006 Preakness Stakes.

Trombetta has been ranked as high as No. 21 overall in wins (in 2014) along with No. 22 in earnings in 2011. To this point in 2019, he’s been a part of 161 starts, resulting in 26 first-place finishes, 24 seconds, 18 third and has racked up more than $1.209 million in earnings. Over the span of his career which features 9,727 starts, Trombetta has made north of $56.51 million in earnings, per Equibase.

READ NEXT: Kentucky Derby Picks 2019: Sleeper, Dark Horse & Longshot Predictions


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