Alison O’Dwyer has had a remarkable string of successes in her four trips to the Thoroughbred Makeover, winning the dressage division three times. But this year, she found what she really wanted in a Makeover mount, in two very different horses. 

“I had said for a couple years, I’d say to my friends and people I know, ‘I really want a horse with a story.’ I know I can get these horses to be competitive [at the Makeover]. But I really want a horse that I can really represent its racing career and have an interesting story to tell,” the Wellington, Florida-based rider said.

She found that in Ratajkowski, a 9-year-old multiple stakes winning mare (Drosselmeyer—Quiet North, Quiet American) who earned $383,390 in 10 starts for owner Gary Broad of Walmac Farm. O’Dwyer’s friend Hillary Ramspacher helps Walmac Farm rehome their retiring race horses, and she made the connections when Ratajkowski, or “Ruby,” was looking for a new career. 

The mare, who O’Dwyer said is pushing 18 hands, didn’t start racing until she was 5. At the end of her 5-year-old year, her connections attempted to retire her to the breeding shed, but despite veterinarians’ best efforts, they couldn’t get her to cycle. 

“She just never cycled, and they couldn’t figure it out,” O’Dwyer said. “Finally somebody pulled some DNA on her, and they were like, ‘Oh, she has an extra chromosome.’ ”

Despite being a mare anatomically, both internally and externally, Ruby has a male Y chromosome. Unlike a lot of intersex equines, Ruby didn’t test positive for excess testosterone during her racing career, which is how many of these cases are discovered, O’Dwyer said.

“Obviously, she was worth a lot of money as a broodmare. I think it was a huge disappointment for [her connections] that she couldn’t go on to make babies,” O’Dwyer said.

Although Ruby’s planned career path changed after her diagnosis, it didn’t change Walmac Farm’s commitment to the mare. 

“I think they are going above and beyond,” O’Dwyer said. “They’re fronting all of her bills; they’ve paid for her to be in training with me. Their goal is to have her have a new career where she can be useful and enjoy life, and they’re paying for it. It’s really remarkable.”

Broad has maintained ownership of the horse, she added. “They don’t ever want to sell her; they want to keep her. They’re very emotionally attached to her. She made them a lot of money as a race horse, but it’s not only that, though. I can tell they’re just attached to her in other regards as well; [it’s] not just money,” O’Dwyer said. “So we’re not exactly sure what the plan is going to be after [the Makeover]. I think the goal will be to find her somebody like in a free lease situation eventually where she can have a career and have a nice little job with somebody, but they want to maintain ownership with her for the rest of her life.”

O’Dwyer has Ruby entered in dressage at the Makeover.

“She’s a very fancy, nice mover on the flat. I think she could definitely have a career in dressage,” O’Dwyer said. “Other than that, maybe a low level hunter—she kind of has the trot of a hunter. We haven’t jumped her a lot; I don’t think she screams upper-level eventing or anything like that. I think she’d be more of an adult amateur dressage horse, maybe some 2’3” hunters, that sort of thing.

“And the nice thing is, even though [her connections] want her to have a career, they’re very dedicated to keeping her,” she added. “So even if it doesn’t work out, they have a spot for her on the farm to be turned out for the rest of her life. They just think a lot of horses would be happier to have a career.”

O’Dwyer added that Ruby has taken to her new path in life quite well, once she finally realized she was no longer a race horse.

“I think she was a bit confused because she was on the track and then off the track and then breeding shed and then she went back to the track,” she said. “I think it took a while to convince her that she was, you know, done-done, for real.”

“She’s very sensitive and super smart; she’s one of the smarter horses I’ve had,” O’Dwyer added. “She remembers a lot and retains a lot. She gets the good qualities [of being a mare] but doesn’t necessarily have the bad ones. She gets turned out with all my geldings, I’ve never heard her squeal, she doesn’t come into heat at all. So she’s like all the good aspects of a mare and none of the bad.”

While Ruby has fulfilled O’Dwyer’s dream to help an OTTB tell an interesting life story as they transition to a new career, her second Makeover mount, Knockemdown, a 4-year-old gelding (American Pharoah—Ancient Goddess; Iffraaj), has given her something she didn’t even know she was looking for: a heart horse.

As with Ruby, O’Dwyer was connected with “Dario” through a friend who worked with the horse’s owners, e Five Racing Thoroughbreds.

“She just happened to call me after I had sold one of my horses, and she’s like, ‘One of my favorite babies ever is retiring. I love this horse so much, would you want to take him?’” O’Dwyer recalled. “He kind of picked me. I normally go for these big, flashy, chromey, fancy horses that I can resell, because I know that’s what people want. He’s plain bay and 15.2,” she said, laughing. 

“He’s just been perfect for me in every way,” she said. “He’s so quiet. He’s super reliable and a joy to ride, and he just suits me. He might not be everyone’s ride, but the more falls I have and the older I get … it’s a very small window for what I really enjoy to ride, and he’s fits in there perfectly.”

And unlike most of her previous Makeover mounts, Dario isn’t for sale. 

“Oh no, he’s mine. Forever,” she said emphatically. “He’s really my soulmate.”

O’Dwyer grew up eventing in Colorado, competing through what is now the three-star level, and moved to Kentucky when she was 18 to be a working student for eventer Dorothy Crowell, who she still considers a mentor and good friend. She got a bit burned out on upper-level eventing and sold or retired her horses, and even considering quitting. 

“And then suddenly over at CANTER, on Facebook or something, I saw this adorable Thoroughbred at Turfway Park for $500. I just jumped in my truck and trailer, found an ATM and pulled out $500 and bought him, and that was it. I was hooked. Every single horse I’ve ever had after that is off the track,” she said.

While her riding focus is on retiring Thoroughbreds, she also has a personal connection to the racing industry through her husband Jerry O’Dwyer of O’Dwyer Racing. Jerry notched his first Grade 1 stakes win in March when 5-year-old Sibelius (Not This Time—Fiery Pulpit, Pulpit) pulled off a thrilling upset victory in the $2M Dubai Golden Shaheen.

Jerry and Alison have a 3-year-old daughter, and since becoming a mom, she’s gotten much more discerning about the horses she rides. And while she currently focuses mostly on dressage, her partnership with Dario is rekindling her love for jumping.

“I’ve become very particular, and the fact that I found a horse that makes me feel this brave, he makes me want to jump, I enjoy riding him. Even if it’s scorching hot in Florida, and I’m running late, and it’s 85 degrees outside, I still want to ride. And that’s because of this horse,” Alison said. “My last two-star FEI horse, by the end, we were a perfect pair, but I haven’t had this in a long time. And I’m gonna hold on to it for sure.”

O’Dwyer acknowledges that it’s quite a mismatched pair that she’s bringing to the Makeover this year. “They are opposites in every way,” she said. “He’s 4; she’s 9. She’s giant; he’s small. She had a great race career. He had no race career. He was retired before his first start as a 2-year-old.”

But what the two horses do have in common are race connections who are invested in their new careers and their attendance at the Makeover.

“And they’re big connections, you know; they’re connections people have heard of, and I think that’s what we need to see more and more, some of these big farms and these big groups come in and, you know, start showing themselves a little bit more if possible,” O’Dwyer said.

She added that she makes sure the horses’ racing owners’ logos are displayed on their saddle pads, because she wants their racing connections to feel a part of their post-racing success.

“It’s one thing to have a picture of your failed race horse on the wall doing dressage, but it’s another thing to have it with your logo on the pad,” she said. “I want them to be proud. I want them to have something to show people.”