Apprentice Jockey Madison Olver Off To Promising Start

Despite the layers of cold water and powder coating her from head to toe, nothing could mask apprentice jockey Madison Olver's bright smile following her first career victory aboard Curbstone (Street Sense) in the sixth race at Aqueduct on Dec. 9, 2022.

It was a surreal moment for the 23-year-old, who just five and a half years prior had never even witnessed a horse race, let alone set foot on the backside of a racetrack or exercised a racehorse.

A native of Fort Collins, Colo., Olver was bit by the 'horse bug' early on as she followed in the footsteps of her equestrian mother Christine. Olver picked up riding and later began teaching riding lessons to younger students, before delving into breaking and training wild mustangs.

After high school, she set out to take her love of horses one step further, which led to Olver's aunt introducing her niece to French racehorse trainer Gina Rarick. Though France would appear to be an extremely far-off base for someone stateside to begin their venture into the world of horse racing, it was a homecoming of sorts for Olver, who had spent part of her childhood living in the country and was fluent in the language.

After a three-month stint in the fall of 2017, Olver was hooked. She returned to France in late 2018, eventually spending two more years there to soak up every experience she possibly could.

“I saw some accidents happen when I was out there and I realized I hadn't quite grasped just how dangerous it could be. The horses take on a whole new meaning of strong, and unless you've been run away with by a racehorse, you don't really know what getting run away with is. That was a whole new game, trying to keep a horse slow, especially when you're behind other horses,” recalled Olver. “Their speed, when you let them go, it's just not something that a horse that isn't bred or trained to do would be able to do. Sometimes you just have to hang on for the ride.”

Though it was daunting at first, and the learning curve was steep, Olver knew she had found where she was meant to be: on the back of a racehorse.

“I definitely wanted to [pursue being a jockey in France], but unfortunately Covid happened and I had a little bit of visa trouble that was exacerbated by Covid, so I ended up coming back over here. But everything happens for a reason,” said Olver.

Eager to get going again stateside, while also working on finishing her degree at Colorado State University, Olver began her search for a new stable to ride for. It led her to none other than multiple Grade I-winning trainer Christophe Clement.

“I was missing France. I love the French and their style of training, and I speak French, so that part really stood out to me. I reached out to them, sent my resume, and they got back to me. They were easily some of the most professional, well-spoken, generous people I'd gotten into contact with on the racetrack,” said Olver. “They flew me out to Florida for a week to do kind of like a trial, and then we talked about where I'd like to go, either Belmont Park or Saratoga for the summer. But they made it very clear that I needed to graduate college before I started working with the racehorses again.”

She did just that, graduating in May of 2021, and headed off to the Clement barn at the Oklahoma Training Track in Saratoga Springs, N.Y., soon thereafter.

“When I showed up to the barn the first day, Christophe goes, 'Okay, did you graduate?' I said, 'Yes, don't worry.'”

As soon as she arrived, Olver got straight to work. Proving her dedication day in and day out aboard many of the promising youngsters that resided in the barn, she quickly worked her way up to become one of Clement's head exercise riders. It was there the young rider formed a special bond with Waterville Lake Stables' homebred filly Derrynane (Quality Road).

“I rode her when she was a 2-year-old and hadn't run yet, and I had just gotten to Saratoga and I was basically a 2-year-old that hadn't run yet, so we learned a lot of things together. She was my first breeze out of the gate here in America, first breeze on the main track at Saratoga, she was my first for a lot of things. Then she went to the Breeders' Cup that year and ran phenomenally,” said Olver.

That summer, Derrynane broke her maiden on debut at Saratoga, later won the Woodbine Cares Stakes and went on to finish fourth in the GII Breeders' Cup Juvenile Turf Sprint at Del Mar, just a length behind winner Twilight Gleaming (Ire) (National Defense {GB}).

“She was also very, very kind. I have her name on my keychain. I felt like her and I were in a little bit of the same place. She's always just been special to me.”

After nearly a year and a half of working and riding in the mornings for the Clement barn, Olver was ready to take her skill set to the track in the afternoon, officially beginning her career as an apprentice jockey. Under the guidance of her agent Joe Migliore, who Olver was introduced to by Clement's son and assistant trainer, Miguel, she made her career debut aboard Flattering Gal (Flatter) in the sixth race on the Nov. 12 card at Aqueduct.

Guiding the filly three, then two wide around the final turn, Olver and Flattering Gal made up ground along the rail to finish third in the 6-furlong, $25,000 maiden claimer.

“When it was going on, it felt very purposeful, like this is what I had been waiting for and afterwards, it all felt surreal that I actually got the opportunity to do it. I was pretty speechless afterwards,” she said.

And less than a month later, in her 16th career start, Olver and her mount Curbstone crossed the finish line 6 1/2 lengths ahead of runner-up Complete Agenda (Curlin). It was the first win for Olver and the second for the Tom Morley-trained gelding.

“It's pretty emotional. If you had told me really not that long ago that I'd get to ride a race, much less win a race, or even continue to have opportunities, [I don't know] that I really would have believed you. I'm very full of gratitude for all of the people that have been willing to help me, just because they're kind and because they want to see people succeed in this sport, [especially] young people,” said Olver.

An extremely gracious young woman, Olver gives all of the credit to those who have supported her along the way, headlined by her standout mentors.

“Miguel really has been my biggest supporter and kept me on this path, even when I found it difficult, thought about going to another track or questioned my own abilities. He also entrusted me with a lot of horses in the morning and there's no better way to learn than on a horse,” she said. “The Clements got me into contact with Joe, who's really been wonderful. He fights for me and he plays a massive part in any success I may have. He knows what's going on, he has an eye for it. And [Joe's father] Richard Migliore's whole philosophy on riding is really wonderful, [emphasizing] how you can be both an assertive rider that wins but also be a horseman. He's very adamant that race riding is an art form, which I think is really cool.”

Despite the intense competition that takes place on the track in the afternoons, amplified amongst the talented jockey colony that resides at Aqueduct, Olver is proud to share her admiration for her fellow jockeys, riders and the trainers that she's gotten to know and learn from in the last couple of months. Trainers such as Orlando Noda, Morley, Antonio Arriaga, Oscar Barrera, III and James Ferraro were some of the first to back Olver, but the list has only grown and continues to do so.

“I really love being able to go to a bunch of different barns and ride a bunch of different horses for a bunch of different people. I've learned so much already just from going around and talking to everyone. You can learn something from everybody and all of those different horses.”

With 46 starts under her belt as of Jan. 6, and four more rides already lined up through Saturday at Aqueduct, Olver boasts a record of two wins, nine seconds and nine third-place finishes, with earnings nearing $190,000.

From her home in Colorado, to the training tracks in France and Saratoga, to Aqueduct's 1 1/8-mile oval, Olver has not only forged her own unique path into the industry, but also continues the legacy of the brilliant female exercise riders and jockeys that came before her.

Her advice to others trying to get in the game? “Everybody deserves a chance to try and the most important thing that I have learned is that it's going to be the people in your corner that are going to help you the most. If it's something that you want to get into, first of all do it, because you can, and listen to what everybody has to say – every hotwalker, every groom, every trainer, every rider, every jockey – because they all have something to teach you. If they're telling you something, it's because they want to see you do well and they want to see you succeed and that's a really cool thing. This industry can be such a rollercoaster of highs and lows, but if you have those lows, don't worry, because there's another high just around the corner.”

Despite the industrywide attention she's garnered, which is only bound to grow, Olver remains humble and hopeful.

“I'm going to see where this ride takes me here. To be honest, I don't even know what I'm doing the following week, so I'm just going to kind of play it by ear, not get my heart set too much on anything,” she said. “My biggest priorities are to love what I'm doing and hopefully have some success while I do it.”