More Than Muscle: Jennifer Stein’s Mission to Lift Up Jockeys

Jennifer Stein is taking her lifelong admiration of jockeys the extra mile.

Long before she would saddle up in a mentorship role for riders, the young girl from Vancouver had already developed a heartfelt fondness for the men and women who ride 1,100-pound equine athletes for a living.

In fact, Stein did not have to look beyond her own family tree to find reverence and respect for jockeys and horse people alike.

“My parents, Floyd Tompkins and Mary-Anne Baumgartner, both trained and were both jockeys before they became trainers,” she recalled. “My grandpa was also a trainer. It goes way back in our family. So, I fell in love with racing when I was just a kid.”

Stein was around the barns at Hastings Racecourse – about a 25-minute drive east of downtown Vancouver – before she took her first steps.

Her parents often share stories and photos from those early days.

“I grew up around riders – my dad even taught (champion jockey) Mickey Walls how to ride. They used to joke that when I was a baby, Mickey sometimes changed my diapers.”

The older she grew, the more fascinated Stein became with the jockeys and their world.

“Even as a kid, I sensed the highs and lows riders faced – injuries, self-doubt, constant weight battles. I didn’t grasp it all then, but it left a lasting impression.”

When she joined the Thoroughbred ranks, her admiration for jockeys continued to grow.

“No matter what job I had, the connection I had with the riders became stronger.”

One of her first racing successes came with a well-regarded multiple graded stakes winner, who starred in both Canada and the U.S.

A dark bay son of City Zip, Alert Bay, by the time he was retired, had fashioned a 15-8-5 from 36 starts, along with $1,342,813 in career earnings.

“I was lucky enough to groom him,” recalled Stein. “He was a colt my dad and I broke together. He ended up racing in California and then came back to me. He won the [Grade 3] BC Derby and the [Grade 3] BC Premier’s, and he went on to win another four graded stakes in California. That horse was pretty special.”

Stein’s path eventually led her to Woodbine Racetrack in 2012, where she worked in Steve Attard’s barn. After a brief stint in Europe with trainer John Hammond in 2015, she returned to Canada and became assistant to fellow British Columbian, trainer Lorne Richards, in 2016.

“I kind of bounced around. I was at Woodbine for two seasons – groomed a nice filly, Tahnee, as a 2-year-old for Steve – and then went back to Hastings, where we won the BC Derby with Alert Bay. Then I went to France for three months, under contract, to work with a flat trainer, John Hammond. He had a filly, Yaazy (IRE), come over to Woodbine to race in the E.P. Taylor Stakes. I galloped her in France, so when she came here, it was really neat to see her run.”

Stein, who was in a relationship with jockey Justin Stein, planned to train her own stable. That pursuit was temporarily put on hold after she gave birth to the couple’s first child, a son, Benjamin, on May 15, 2020.

On September 21, 2021, she and Justin were married.

In the spring of the following year, she returned to Woodbine, this time with her trainer’s license, after working in Florida over the winter with Justin for Canadian Horse Racing Hall of Fame trainer Josie Carroll.

On November 4, 2022, she saddled her first starter, Dreamingof Jeannie, a 3-year-old daughter of Frost Giant. Her most notable victory came just over three weeks later with Thebackstretchdude, a hard-luck son of Old Forester, who delivered Stein her first training win.

Fittingly, Justin was in the irons for the milestone.

“That is something I will never forget – it was absolutely perfect,” recalled Jennifer.

Much has changed for both since that treasured moment.

Jennifer stepped away from training at the close of the 2024 Woodbine season. Around the same time, Justin – who rode 1,440 winners, including the 2012 Queen’s Plate victor Strait of Dover – retired from the saddle and is now an Ontario Racing Commission steward.

It was Justin’s decision to retire from race-riding that motivated Jennifer to chart her next career move.

A recurring thought guided her throughout that process.

“I was thinking where my compassion and empathy for jockeys would lead me. I started thinking about riders, how they have to go through so much on their own, some who don’t have immediate family close by, and others who struggle with their weight.”

She also thought of Michael Baze.

The up-and-coming rider, who won more than 900 horse races in a nine-year career, died from an accidental overdose on May 10, 2011.

Jennifer had spoken with Baze one day prior to his passing.

“He sounded really good – you could hear hope in his voice. That’s why the news hit so hard the next day. It was devastating.”

Stein thinks of him often, even more so now in her new role as a mentor to Canadian jockeys.

“I do feel as though I was destined to do this. The connection for all riders is that there are not a lot of people who you can talk to about your struggles, someone who would have an understanding and tie to their world.”

A former standout soccer player in her native British Columbia, Stein has long felt a kinship with the ultra-competitive nature that is part of a jockey’s DNA.

“Being a seriously competitive athlete myself, I always found a deeper connection to the sport through jockeys, and I appreciated them. That competitive streak has kept me in the sport, but instead of training horses, I’m training jockeys.” ​

Stein’s approach covers everything from nutrition and exercise to mental health.

“I want them to count on me to help them out. My mom had dense bones, so she struggled with her weight. I know a lot of other riders who have the same problem.”

“With my knowledge of nutrition as well – it’s hard to find a personal trainer that specializes in jockeys. You need an in-depth understanding of the life of a rider. So many jockeys can’t eat what most people would deem as a regular meal. One of the things I am focusing on is providing riders with the nutrition they need. Instead of grabbing a chocolate bar or chips, I will bring something else instead. That could be an active-muscle collagen smoothie with some flax and chia seeds, or oatmeal bars – things they can fuel up on between races.”

Skye Chernetz, who has won 215 career races, is grateful for Stein’s understanding of a rider’s nutritional needs.

“Jen has always been health conscious – she is really good at making snacks and meals that taste good and have many health benefits,” said the Woodbine-based Chernetz, who has been close friends with Stein for over a dozen years. “I think it’s important for jockeys to understand nutrition and what works best for their body type.

“She has also given me some natural products like a creme ointment and bath salts for sore muscles that are extremely helpful.”

Beyond the nutritional and recuperative aspects of her playbook, Stein is helping riders, including Eswan Flores, navigate the range of emotions tied to their career.

It is something she saw first-hand during Justin’s time on the racetrack.

“I have seen the highs and the lows in lots of riders. Justin obviously dealt with them. It comes with the territory, but that doesn’t mean you have to walk that road alone. If you are riding your races, listening to the trainers and your agent, and are still getting beat, that is just the way the game is. That’s why it is important to navigate your way through difficult moments. It does end and it does get better.

“One race you are the winner’s circle, the next you are off the board with the favourite – the highs and lows can be separated by minutes some days.”

Jennifer, in racing parlance, is taking a trifecta approach when interacting with riders.

“They can get quite discouraged if they don’t have someone to talk to, so that’s why compassion, empathy and just listening are so important for me. I want to help mentally prepare them every day to do the best they can and be at the top of their game.” ​

Getting riders comfortable enough to open up and engage in conversation, she noted, is a crucial component in her relationship with the riders.

She is committed to encouraging that dialogue.

“If a rider is struggling about this or that, they may feel hesitant to do it for a number of reasons. What they do for a living is tough, mentally and physically, and there is perhaps a stigma that they need to stay tough, be silent, and battle through whatever is affecting them.”

Flores, who reached the $2-million plateau in purse earnings for the second time in the past three years in 2024, is grateful for Stein’s efforts.

“We know our jobs, we understand how to read the form and anticipate how a race might unfold,” said Flores. “But taking care of our bodies in preparation of race day and after the races or off days is something that I think every jockey needs to focus on because we take it for granted. But now that’s not the case for me.”

Working with Stein has been an eye-opening experience for the lifetime winner of 542 career races.

She has helped him to reach new heights, literally.

“I’ve always been good at the fitness and power side of my race preparation,” said Flores, who has taken up indoor rock climbing. “My brand is being a physical rider. But as a rider, we put our bodies through so much and I am really understanding the importance of how I feed and treat my body. Jen has been great to work with and I’m seeing benefits already.

“Jen has provided me with a strong nutrition plan and ways to focus on my mental health – it feels great.”

As Stein works to expand her client list over the coming months, there is a possibility that a familiar face might one day approach her for counsel about life in and out of the irons.

“It looks like Ben could be on the path to being a jockey,” Stein said of her soon-to-be 5-year-old son. “I think having him grow up around the jocks, learning how they work and what I do to assist them will help both of us in the future if he does become a rider.”

For now, she will work with those who continue to inspire her.

“I have always felt a bond with jockeys. Anything I can do to help them means the world to me.”

Chris Lomon, Woodbine