Dewey Square a Thoroughbred of Many Talents


Dewey Square and Isabela de Sousa at the Thoroughbred Makeover. (Photos courtesy of Isabela de Sousa)

Bringing in a high bid of $575,000 as a yearling, the amount wasn’t enough to buy Dewey Square from his breeder Siena Farm and he returned to the Kentucky farm before starting his racing career. 

The move paid off with Dewey Square spending some time on the Kentucky Derby trail, even finishing third in the Grade 2 Kentucky Jockey Club Stakes. But after nearly three seasons of racing, Dewey Square was retired in 2014 and ready for a second career. 

Read about Dewey Square on the Triple Crown trail

That’s where 14-year-old Isabela de Sousa and her father Sergio de Sousa of Hidden Brook Farm came in. 

“My dad Sergio de Sousa runs Hidden Brook farm and Siena Farm, the farm that had Dewey, they are right across the street from us,” Isabela said. “We were looking for a project and instead of putting Dewey in a claiming race, we decided that we’d take him so they gave him to us as a project.” 

After getting Dewey Square at the end of 2014, the de Sousas turned the then-4-year-old gelding out for the winter. Starting him back to work in May of 2015, Isabela soon learned how willing Dewey Square was. 

Teaching him his new job also allowed de Sousa to strengthen her training skills. 

“Dewey is a pretty simple horse and he tried to do everything that I asked him,” she said. “But one of the biggest challenges for us what that since I’m only 14 I’m still learning and I would make a few mistakes here and there so it was really Dewey who would be patient with me. He’d listen to what I’d ask him and he’d try to do everything I asked him … that’s what I love about him is he really tries for me. We were both learning together.” 


Introduced to the Retired Racehorse Project’s Thoroughbred Makeover competition by one of her dad’s friends, Isabela and Dewey Square were a late entry in the competition in the Show Hunter and Show Jumper divisions. As a show jumper herself, Isabela had experience in the disciplines and Dewey Square’s way of moving and jumping ability made those divisions the logical choice.  Paired with the idea of seeing how much progress Dewey Square had made since May and getting more Thoroughbreds in the competition, joining the Makeover made perfect sense to Isabela. 

Competing against 33 other Thoroughbreds in the Show Hunter division and 43 in the Show Jumper division at the Makeover’s late November show, Dewey Square showed that he wasn’t just a talented racehorse. 

While Isabela blames herself for the mistake that had them finish third in the Show Hunter division, the Show Jumper division was where they ruled. 

Coming into the final round of the event with a score of 80, Dewey Square and Isabela were ranked third. But the pair put in the best round of the Finale, earned a score of nine to boost them up to a final score of 89. The score was good enough for first place, giving them top three finishes in both divisions they competed in. 

“I felt really proud, I was so proud of him,” she said. “He loves going in the ring with a lot of people and I was really proud of him going around the ring acting like a big boy and being brave; just doing everything that I asked him to do. I was really ecstatic, and all of our hard work paid off. It was just such a happy moment for me being the rider and the trainer and seeing the transformation from the beginning of the year so it was an incredible moment for me.” 


Isabela was impressed with the first Makeover held in Kentucky and the opportunity to meet competitors from many different disciplines. The ability to show off the versatility of the Thoroughbred breed was also a major attraction for her with a variety of disciplines taking place at the event from polo to jumping to barrel racing. 

“The thing I really love about [this breed] is their great work ethic and they just want to please you. They’re very quick learners about everything,” she said. “They have a great mind and since they are very athletic, everything you really want them to do from polo to hunter/jumpers or anything, they can really do it. You just have to teach them how and they’ll put their mind to it and they’ll do anything you ask them to. So they’re a very willing breed.” 

Dewey Square is currently turned out at Hidden Brook for the winter where he’s relaxing and growing. In the spring he’ll head up to Maryland where he’s entering eventing training with his new owner. But for Isabela, the impact he’s made on her life in the last year won’t be forgotten any time soon. 


“Dewey is a once-in-a-lifetime horse for me,” she said. “I’ve never really gotten an experience like this and it’s an experience that will stay with me forever. Dewey is just a big part of my life right now, he’s incredible. The Thoroughbreds, I can’t say enough good things about them, they are great and I would really like to see them start entering the show jumping world a lot more and being given more second chances like the Thoroughbred Makeover gives them.” 

The Thoroughbred Makeover returns to the Kentucky Horse Park in October of 2016 with 488 trainers sending in applications for 741 horses this year. The event is capped at 500 horses with the list of accepted horses to be announced by the Retired Racehorse Project on Feb. 15, 2016.

newsletter sign-up

Stay up-to-date with the best from America's Best Racing!