Another Thoroughbred Makeover is in the books, and what a week it was. Between the rain, the long days, and the incredible athletes we competed against, it’s safe to say this year’s event was one for the memory books. Bringing both Imposing Ruler – aka “Henry” – and Gray Magician made for a full and rewarding experience, and I couldn’t be prouder of how both horses handled themselves.

'Henry' grazing peacefully. (Courtesy of Lindsay Gilbert )

For Henry, the Makeover felt like the perfect culmination of all the growth he’s shown this year. Thinking back to his very first show, it’s amazing how far he’s come. At that debut, he was overwhelmed by the bustle of the showgrounds – the sound of the announcer, the activity around the ring – and it took him a while to settle and focus. Fast forward to the Makeover, and it was like watching a different horse. He hauled over in the pouring rain, settled quietly in his stall, and warmed up in a downpour without batting an eye. When it came time to jump, he confidently tackled everything I asked of him. One of my favorite moments from the week was watching him hand graze peacefully with my 6-year-old daughter – a sweet reminder of how kind and genuine his temperament is.

In the show ring, Henry took everything in stride and jumped in beautiful form, showing off just how much potential he has as a future jumper. We did have one green moment when he got a little nervous, and I opted to circle to give him a chance to regroup. It might have cost us a few points on the scorecard, but it was absolutely the right call for him at that moment. We ended up mid-pack in the results, but I couldn’t be prouder. The progress he’s made from his first show to this milestone event speaks volumes about his heart and his future.

Gray Magician’s week was equally special – though in a very different way. He arrived at the Makeover with quite the entourage, including his race connections who had claimed him back after his racing career and placed him in retraining specifically for this event. It was a true full-circle moment, and their dedication to his second career has been nothing short of inspiring. In the weeks leading up to the Makeover, Gray attracted quite a bit of attention from the media due to his remarkable story – after all, not every Makeover horse can say they ran in the 2019 Kentucky Derby. I had the opportunity to be interviewed by several publications about his racing career, his transition to sport horse life, and the commitment his owners have shown to ensuring he thrives in his new role.

What stood out most to me was how genuinely invested the Thoroughbred community was in his journey. So many people followed along, cheered him on, and celebrated his progress – it was heartwarming to see that kind of collective pride in a horse’s second career.

Due to the weather on Tuesday afternoon, Gray missed out on some schooling opportunities, but he stepped into the show ring and handled everything like the seasoned professional he is, despite not jumping a single fence in the days prior. In the jumper ring, he showed his athleticism and scope, making light work of the courses while I just enjoyed the ride. In the hunter division, I’ll admit I was well outside my comfort zone – it was my first time showing hunters at a large venue like this, and my inexperience probably kept us out of the ribbons. But Gray did exactly what I asked of him, proving how kind, willing, and adaptable he truly is. His performance earned him top-20 finishes in both divisions, a testament to his quality and his team’s dedication.

The Makeover is always a whirlwind – long days, unpredictable weather, and the thrill of being surrounded by so many talented off-track Thoroughbreds – but this year reminded me why it’s such a meaningful event. From Henry’s incredible growth to the joy of seeing Gray Magician’s connections experience their horse’s athleticism in a totally different way, it was a week full of pride, gratitude, and inspiration.

The Jockey Club supports many aftercare initiatives including the Thoroughbred Aftercare Alliance, the only accrediting body in aftercare, and Thoroughbred Incentive Program (T.I.P.), which encourages the retraining of Thoroughbreds into other disciplines upon completion of careers. View all of the initiatives supported by The Jockey Club.