Thoroughbred Makeover Diary: Foundational Work Pays Off With First-Show Success

Aftercare
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Imposing Ruler (shown competing at a recent show in Paris, Ky.) and Gray Magician have both progressed in their training with Lindsay Gilbert as they prepare for the fall 2025 Thoroughbred Makeover. (Rachel Milewski photo)

June was a big month for the dynamic duo that is Gray Magician and Imposing Ruler. Both boys tackled their first horse show last month, which also happened to be Gray’s first time off property in my program. While taking things slow is a key component of my program for Thoroughbreds coming off the track, it can be hard to put on the metaphorical blinders and focus only on my mounts. After watching others tackle first shows earlier on in the year, I’ve been fighting thoughts of feeling behind.

However, the several Makeovers I have completed in the past and numerous young horses I’ve developed in general have ingrained in me the belief that it is truly a marathon and not a sprint. The slow and steady foundational work seems to have paid off, as both boys were phenomenal in the show atmosphere.

Gray Magician (Rachel Milewski photo)

Gray Magician was cool as a cucumber from the moment he stepped onto the trailer. I’ve found with war horses, sometimes they are so exposed to things on the track that nothing we can throw at them in the sport horse world seems to bother them, but other times they associate traveling with racing and their first few times off property can be a lesson in relaxation. Gray has shown me time and again in his training that he falls into the former category, never batting an eye at anything.

For his first show, we kept it light and easy – entering just the 2’ Jumpers. I was pleased that the local schooling show we attended, at Scheffelridge Farm in Paris, Ky., had a lovely course with decent amounts of fill and several great questions, including a fun 2-stride combination. Gray read (and responded to) all of the questions with ease! He even settled into a wonderful, relaxed canter that makes me think he may want to try his hand at the hunters next time out.

Imposing Ruler, aka Henry, however, thought horse showing was a much more exciting endeavor. While not his first time off property, Henry was only lightly raced and is still learning about the ways of the world. Because of this, I entered Henry in a division with slightly larger fences, but that went later in the morning and would give him plenty of time to adjust. I’m glad I did, as standing ringside watching horses canter by, hearing the announcer and clapping spectators rattled him initially. But, by the time we tacked up he was quietly grazing and unbothered by the atmosphere.

Henry absolutely blew me away with his willingness in the ring. At 4 years old and only 14.2 hands, a .65m fence at his first horse show could have easily seemed like an endeavor of Olympic proportions. But, what he lacks in size he certainly makes up for in scope and heart. He eagerly tackled the colorful fences, rollback turns and combinations. He really enjoys his job and just got more confident with each fence!

With two newly-minted show ponies, I am eagerly making plans for the rest of the summer to solidify their paths to the Makeover. Additional schooling shows in July will help me determine if Gray truly wants to try his hand at the hunter ring, or stick to jumpers (or both!). Henry will do a bit of dressage at home, go cross-country schooling and head to a jumper show with a bit more atmosphere before we try our hand at a full event in August.

Regardless of the path, I will keep taking it day by day, living life in the slow lane and letting each horse tell me what they enjoy doing. My hope is that, in making no assumptions or forced plans for the boys, we will arrive at the Makeover with happy, healthy horses that are well-rounded and excited to enter whichever ring they choose.


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.

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