A picture-perfect first win for trainer Stein

December 15, 2022

Justin Stein and Thebackstrechdude winning the first race on Nov. 27, 2022, at Woodbine (Michael Burns Photo)

Chris Lomon, Woodbine Communications

TORONTO, Ont. – Jennifer Stein was, at least outwardly, far less restrained than those standing behind her, and the jockey aboard the eye-catching chestnut colt. 

Standing in the owner’s box in the Woodbine grandstand for the first race on November 27, the trainer of Thebackstretchdude, a son of Old Forester, watched intently as the gates opened on a rainy afternoon at the Toronto oval. 

Dialed-in on the horse with the yellow saddle cloth and the jockey wearing the blue silks with white stars, Stein couldn’t help but notice the emphatic voices less than an arm’s length away from where she stood. 

“They were screaming from the time the race started,” recalled Stein, of owner Isaac Waxman and his wife, Tess. “That emotion, it really is what this sport is all about. They’re standardbred owners and trainers, and this was their first thoroughbred win, so it’s a different kind of rush for them.” 

And, also for the woman who handed the reins of the Ontario-bred to her husband, top Woodbine rider Justin Stein. 

A length clear after the opening quarter of the 5 ½-furlong maiden race on the Tapeta, Thebackstretchdude repelled a brief outside challenge running on the turn and then widened his advantage to 2 ½ lengths at the stretch call. 

At the wire, the slight 5-2 choice was 1 ¼ lengths clear of his nearest rival, a victory punctuated by Stein, the rider, turning his head towards the grandstand, broad smile on his face, and right index finger pointing at the rookie gelding. 

Stein, the trainer, couldn’t have penned a better script for her first training win.     

“The owners, they weren’t expecting him to win. There was a time when they weren’t even expecting him to make the races. I kept it quiet the closer he got to racing.” 

An understandable approach after the up and down journey Thebackstretchdude took to get to the starting gate. 

A $3,000 purchase by Waxman and Stein at the 2021 CTHS (Ontario Division) Canadian-bred Yearling Sale, the horse, bred by Anthony B. Russo & Leslie L. Russo, would need some time before making it to the races was even a consideration. 

“There was a lot of touch and go with him, so we turned him out. We pushed on and took it day by day. I never got too excited about it [making it to the races] because I knew anything could happen on any day. They will be able to tell you when they are ready to go.” 

In the days leading up to 1:21 p.m., just over two weeks ago, Thebackstretchdude had given every indication to his connections that he was indeed ready. 

“I love the fact that it was him that gave me my first training win. That made it even more special. You look back to how things all started, and it really does become something you never will never forget.” 

Horses and horse racing are in Stein’s DNA. 

Growing up in Vancouver, she was introduced to Thoroughbreds through her parents, both of them well-known names at Hastings Racecourse.   

“My parents, Floyd Tompkins and Mary-Anne Baumgartner, both trained and were both jockeys before they became trainers. 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.” 

At that time in her life, only one other pursuit matched strides with her affinity for horses. 

“Soccer and horses were what I lived and breathed. I played on some pretty competitive soccer teams. We were undefeated in two or three seasons. We won Coastal Cup championships a couple of times.” 

Stein soon found success off the pitch. 

And it came on the hooves of a multiple graded stakes winner, who made his mark in both Canada and the U.S. 

A dark bay son of City Zip, Alert Bay would carve out a brilliant career, one that yielded a record of 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.” 

Jennifer Stein and Thebackstretchdude. (Photo courtesy of Jennifer Stein)

In 2012, Stein came to Woodbine and started working in the barn of Steve Attard, the same year her future husband would win the Queen’s Plate (now known as the King’s Plate) with Strait of Dover. 

Three years later, Stein headed to Europe. 

“I went to France in 2015. 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 steeplechase and 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.”  

In 2016, Stein worked as assistant to Woodbine trainer and fellow British Columbia native Lorne Richards.  

Learning the ropes from the veteran conditioner proved to be a game changer in her pursuit of a training career. 

Advice was plentiful and welcomed. 

“From Lorne, I learned to just be patient, that if your horses do come around, they will run for you. Just be patient and do right by them. I learned that from other trainers too, to put the long, slow miles into them.” 

Stein’s plans were put on hold, temporarily, after she gave birth to the couple’s first child, a son, Benjamin, on May 15, 2020. 

In the spring of 2022, 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, she saddled her first starter, Dreamingof Jeannie, a 3-year-old daughter of Frost Giant. 

Under jockey Leo Salles, the chestnut filly finished third, a head back of the runner-up, in the 1 1/16-mile Tapeta race at Woodbine. 

“She’s a neat, little filly. She came from Fort Erie, and they sent her here for some longer races. She had some things going on with her, but we got them sorted out, and she ran so well. She’ll love grass and the farther, the better. It was nice to have her run third. We were really happy.” 

Two work buddies just chillin’. (Photo courtesy of Jennifer Stein)

Just over three weeks later, that happiness was usurped by Thebackstretchdude’s milestone score. 

The finish of the race remains etched in her mind. 

“Justin gallops him every day and breezes him for all those breezes. He had a lot to do with the victory. It was special to him, and I think everyone saw that the way he patted him and celebrated at the wire. It was also nice to have my best friend, Holly [Murray] be part of it. We worked together out in Vancouver, we won the BC Derby together, our parents raced horses together. It was cool that she had paddocked for me that day.” 

With the 2022 Woodbine Thoroughbred season having reached the finish line, Stein will take some time to decompress before turning her thoughts to next year’s meet, one with a proposed starting date of April 22. 

Plans, both in the short and long term, are already in place. 

“I’d like to start next season with seven or eight, and by the end of year have 10 decent horses to go away with for the winter, to stable somewhere south and race the whole year. That’s my main goal. Winning an Ontario Sales Stakes with Thebackstretchdude would be another one. There is a lot to look forward to.” 

And not just in her barn on the Woodbine backstretch. 

Making the most of the great outdoors, even during the winter, remains a constant in her life outside of racing.  

“Justin and I like to cook together. We take out dogs on some pretty cool outdoor adventures and we snowboard. We’re pretty outdoorsy. We visit our riding horses, and obviously, spend time with Benjamin. We have our hobbies to keep the racetrack and our personal lives separate.” 

There will still be times, however, regardless of where she finds herself, when she will take a moment to relive that early afternoon at Woodbine, a grey day with a much sunnier outcome. 

When she does watch the race replay, Stein will no doubt smile at the recollection of the sights and sounds throughout the race, all 1:04.72 of it. 

“Hearing how happy the owners were, seeing Justin celebrate at the wire and knowing how far this horse had come… I don’t think I could have written it any better.”    

@JakeBlues23231 @jonathanstettin @PastTheWire hat trick, unbelievable!

Bill Mentes @drbillym View testimonials

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