Maddy Olver has spent most of her adult life beating the sunrise to the backstretch. To the young horsewoman in the pre-dawn twilight, it all felt necessary. Some dreams were worth sacrificing for, and becoming an apprentice jockey this winter made it all worthwhile.
“At the beginning, I wasn't sure what it would look like, I wasn't sure necessarily if I would be able to,” Olver said. “I wasn't sure where I would go or how long it would last. There were a lot of question marks, but I just knew it was something I at least deserved the chance to try to do.”
In her first months as a jockey, Olver has earned 10 wins at Aqueduct Racetrack, an impressive achievement for the 23-year-old on such a competitive circuit. The statistic does not come close to telling the full story, however, as Olver's success this winter was only made possible by years of work seen by almost no one.
When people think of riding racehorses, they conjure images of championship glory under a setting sun at events like the Kentucky Derby or Breeders' Cup. But this is only the reality for a select few, and to get there, riders must first earn their silks riding in early-morning workouts. Some never make it to the races.
Before she ever entered the winner's circle among the afternoon crowds, Olver first had to impress salty horsemen in front of empty grandstands. These connections have the power to make or break a rider's career.
“I'm not from a racing family,” Olver said. “All the support that I have comes from people who don't owe me anything. They're just doing it because they want to see me succeed.”
Olver, a Colorado native, rode horses from an early age, but her experience in racing was extremely limited before she traveled to France in 2017. Fresh out of high school, she worked as an exercise rider for trainer Gina Rarick and quickly fell in love with the sport. Two years later, she accepted a position in the U.S. for champion trainer Christophe Clement. Without any preexisting connections in the sport, she couldn't have asked for a better place to start in her stateside return.
While working for Clement in 2021, a bond with trepidatious 2-year-old filly Derrynane came to define Olver's body of work as an exercise rider. She quickly developed a reputation for profound care and understanding in the saddle during training. Derrynane went on to finish fourth in that year's Breeders' Cup Juvenile Turf Sprint under jockey Joel Rosario.
“Derrynane was a little bit of an anxious filly with plenty of talent and speed,” Clement said. “Maddy kept the filly going without boiling over, without going the wrong way mentally. She was not an easy filly to train … even if she was anxious, she was always manageable with Maddy.”
Though Olver began working in New York through Clement's stable, it didn't take long for her to accept other training assignments after receiving her jockey's license. In fact, her work for smaller stables was what eventually led her to racing opportunities through jockey agent Joe Migliore.
Migliore, son of retired rider Richard Migliore and agent to several respected riders on the New York circuit, began delivering a different kind of sales pitch to convince trainers to give Olver a chance going into the 2022-23 season at Aqueduct.
“Advertise them as young, hungry, learning, improving,” Migliore said. “It's a much different pitch than a veteran rider for sure.”
It all started with Flattering Gal, a struggling filly trained by up-and-comer Orlando Noda. She was no Derrynane, displaying very little in her first two career starts on dirt, but had responded well to Olver in the morning. Noda was willing to take a chance when Migliore came calling. Olver noted that she was simply “trying to survive” in that first race on Nov. 12, but when a gap opened on the rail, she took full advantage and finished third at 31-1 odds.
“She got along good with the horse, and from there on out, she just kept coming back and working horses for me,” Noda said. “Whenever I have a shot, I always try to use the bug weight, and she has good work ethic in the mornings and whatever we ask her to do in the race, that's what she tries to do.”
For nearly a month, Olver toiled away, playing the part of hungry apprentice to perfection with a handful of mounts each week. She earned solid finishes in low-level races but her first win proved elusive. Fortunately for her, trainer Tom Morley was willing to try anything for his horse, Curbstone.
To Morley, a keen-eyed trainer from the United Kingdom, Curbstone was a turf runner based on his appearance and pedigree. But his instincts weren't serving the horse well.
The 3-year-old gelding's first race for Morley's stable on Nov. 19 was a disaster, a 38 ½-length defeat in an allowance race on the Aqueduct turf. Hall of Fame jockey Javier Castellano rode Curbstone that day and told Morley afterward that he simply didn't seem interested in racing. Something had to change, even if it meant taking risks.
For his next start on Dec. 9, Morley entered Curbstone in a $40,000 claiming race at 1 ⅛ miles on dirt. In addition to the surface change, it was also the first time the gelding raced for a price tag. At an uncertain time for the underachieving gelding, it only made sense to let him compete with less weight and his regular exercise rider. Olver got the mount.
“Honestly, my expectations were very low,” Morley said. “I was just hoping we could reignite this horse's love of racing, and we certainly seemed to do that … I can't remember the last time I smiled as wide a smile after a [claiming race].”
When Curbstone romped home to win by six lengths that day, it was impossible to nail down the exact cause. One thing was undeniable — Olver had done something right to earn her first win as a jockey. She rode Curbstone again on Jan. 28 and won even more impressively by 12 ¼ lengths.
Such commanding victories will certainly raise Olver's stock going forward, but despite all her success at Aqueduct this winter, she will not be able to stay in New York much longer. In the spring, some of the best jockeys in the country return to the circuit and form one of the strongest rider colonies in the world. Any race at Belmont Park or Saratoga Race Course can include 10 jockeys destined for the Hall of Fame. Many younger riders simply can't compete for opportunities.
With the colony returning to New York, Olver will begin looking for mounts at Monmouth Park in New Jersey. It's a common move for New York riders pushed to the fringe — for one reason or another.
Olver's identity as a woman in racing is still a rarity despite a growing movement over the last three decades. Talented female riders like Julie Krone and Rosie Napravanik have been present in the sport for some time, but Olver still finds that women in the industry have to work harder to receive the same opportunities.
“I think it still impacts any woman exercise rider or jockey now,” Olver said. “I think that if they have the opportunity to use a girl or a guy, they're going to choose a guy. They naturally might be a little bit stronger, and people know that and they're going to want, in their opinion, the strongest rider on a horse.”
Though many men in the sport have been willing to give Olver chances on the track, it's no coincidence that the young rider's career has quietly been propelled by women as well.
She received her first exercise riding job in France from Rarick, a female trainer. Noda, who gave her her first mount as a jockey, considers his wife, Melani Cruz, to be an integral member of his operation and appreciates women's abilities in the sport. Morley was hired to train Curbstone by owner Patricia Moseley, who also had to approve her trainer's choice of jockey. After winning her first race, Olver was interviewed by NYRA broadcast analyst Maggie Wolfendale, Morley's wife.
In between races at Aqueduct, Olver spent time learning from fellow jockeys Jackie and Katie Davis, daughters of trainer Robbie Davis, in a locker room specifically for women. The latter Davis sister is married to jockey Trevor McCarthy, another client of Migliore's. It's an insulated industry, and may not be without prejudice or preconceived notions, but Olver has managed to form a highly supportive network.
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If you appreciate our work, you can support us by subscribing to our Patreon stream. Learn more.“Maddy is a jockey in my mind,” Morley said, his emphatic tone conveying more than the words themselves. “She's not a lady jockey but an apprentice jockey. She rides every bit as well as the apprentice boys, and the fact that she's a lady bug rider never played into my mind at all. I've watched the horses respond to her in the morning and they were obviously doing so again in the afternoon.”
At some point, Olver will shed her weight advantage as she continues to rack up wins. She will have to accept low-level opportunities at tracks further down the East Coast with the intent to someday return to New York full-time. It could be a long road.
Her life as a jockey has just begun, but after earning the respect of seasoned professionals in one of racing's most competitive locales, challenges thus far have had a way of shrinking before Olver. She focuses on the joy of riding and a love of the work. Clement's concise praise of his former rider could carry her further than any natural talent.
“We very much liked, altogether, her outlook on life and outlook on the job,” Clement said. “Basically, to make a long story short, she's just a good person. It's very refreshing when you work with good people.”
Patrick Moquin is a freelance journalist from Oceanside, New York. He is currently studying at the Columbia Graduate School of Journalism, where he will receive a master's degree in 2024. He graduated from Fordham University in 2022.
As a Long Island native, Patrick has spent many spring and fall weekends at Belmont Racetrack, enduring a moderate horse allergy for his favorite pastime. He is also an avid New York Mets fan and struggling chess player, completing a trifecta of occasionally heartbreaking life choices.
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