“It brings me much pleasure to see Jamie excelling as a trainer; he’s not just a good horse trainer, but a true gentleman.”
Hall of Fame trainer Mark Casse is referring to James ‘Jamie’ Bentley Begg, who notched his first Woodbine stakes victory over Thanksgiving weekend with Shotgun Wedding. The Canadian breeder-turned-trainer worked for Casse for six years before starting his own training business, Begg Racing, which operates out of Woodbine and Belmont racetrack.
On Saturday, October 11, Begg’s trainee Shotgun Wedding secured the Ontario Damsel Stakes with jockey Keveh Nicholls. The three-year-old Mendelssohn filly is jointly owned by Begg’s father, Jeff (under Windways Farm), Begg Racing, and Upland Flats Racing.
During the post-race stakes interview, the winner’s circle was warmly lit by the presence of Begg’s family including his twins, Easton and William, his fiancé, Astrid Caie, and Barbadian jockey Nicholls, who Begg lightheartedly introduced as part of the family unit as well.
Begg’s current Woodbine string includes ten horses. He also has five horses just south of the border at Belmont.
Walking into his barn on the backstretch, you are quickly greeted by Begg’s dedicated assistant, Emily Fisher, and some of his hard-working staff, such as Courtney and Alfredo.
At 38, the trainer has done almost everything under the sun including show jumping, playing polo, foaling mares, breeding horses, handling stallions, working for a couple of Hall of Fame trainers, and now running his own operation.
Born in King City, Ontario, both Begg’s father, Jeff, and grandfather, James, have ties to horse racing as well – whether turning a racehorse into a grand prix showjumper or owning and breeding racehorses over the years. Both his brothers, Ryley and Andrew, also played polo.
In 2007, at 20, Begg graduated from the Irish National Stud breeding course in Kildare, Ireland.
“You pretty much work for the farm, but in the evenings you have a lecture. Our vet would have lectures with us for a couple of weeks going through repro [reproduction], but then they would have a bloodstock agent come in. Different people came in from throughout the industry and would leave business cards, so if that was the area you wanted to go, they could hook you up with a job out of the course.”
Jamie with El Alacran. (Hayley Morrison photo)
Begg expanded on his time in the program that runs six months. “You go through all the yards, you handle the stallions, you do the foaling for a couple of weeks, the barren mare yards. And it’s cool, I did the course with Ken Sweezey who also trains in the U.S. and till this day we are still friends. I’ve sent him horses down to Florida or here or there.”
After returning to Canada, Begg worked as an assistant manager for the now-defunct Gardiner Farms in Caledon East. “I did all the foaling; I galloped there and handled the stallions,” Begg said.
Two years later, Begg developed Kingstead Stables and ran that operation for several years before deciding to close its doors due to the Slots at Racetracks program ending. Begg decided to shift gears again and work under two Hall of Fame conditioners, Roger Attfield and Mark Casse.
“Casse bookended Attfield,” Begg acknowledged. “Their training programs are very different. Roger is more European-based, and Mark would be developing dirt horses. Great horsemen, both of them.”
“I ended up taking a job with Mark rubbing horses one winter,” said Begg. During his time within the Casse operation, Begg went from grooming to running strings and eventually overseeing the daily training of several notable horses such as 2019 Belmont Stakes winner Sir Winston.
One mare that was particularly close to his heart during that time was Catch a Glimpse. The City Zip mare was owned by Gary Barber, Michael James Ambler and Begg’s father, Windways Farms.
“Catch a Glimpse was actually my dad’s horse. He bought it and then sold it – Gary bought into it with his partners. I was actually supposed to buy in as well, but because I had just let go of all my broodmares I didn’t want to make an investment right away again. So I turned that down, which was probably a pretty big regret,” Begg said ruefully.
In the fall of 2015, at Woodbine, Catch a Glimpse broke her maiden and just over three weeks later won the Gr. 2 Natalma Stakes. In October of that same year, the stakes champ captured the Breeders’ Cup Juvenile Fillies Turf race at Keeneland.
“It was cool enough to train a Breeders’ Cup winner. It was actually Mark’s first Breeders’ Cup winner as well. Tepin [another Casse trainee] won the next day, and she always got the forefront over [Catch A Glimpse], but that filly was pretty nice,” Begg said.
In 2020, Begg went out on his own as a trainer and over the last five years has steadily grown his business, running horses at several U.S. tracks and in Canada at Woodbine. In 2023, he secured his first stakes win with Greavette in the Finest City Stakes at Presque Isle Downs.
Two of his Woodbine stakes-placed runners, Pageant Queen and Sipping History, are entered in the $100,000 South Ocean Stakes to be run on Sunday, October 19. With both fillies coming off final works last weekend, Begg is clear about where he’d liked to see those runners finish up at this year’s meet.
“I think that Pageant Queen is going to end up being more of a two-turn horse, so the seven-eighths may help her with a little added distance. We were a little disappointed with how she ran last time, but the Princess Elizabeth at the end of the year will probably be what we point to. We have really wanted to try to get her on the grass it just hasn’t come to fruition yet.”
“With Sipping History, she has run quite a bit this year, so we will either run there or skip that, but she probably only has one more in her before we put her away.”
Begg’s future plans include adding more horses to his current operation. He recently purchased a couple of yearlings out of the 2025 CTHS sale. “We bought Sipping History’s half-sister by Reload, and we bought a Souper Speedy out of mare named Zelkova. They are at Amplify [Stables] right now and then they will go down to Martin Rivera in Ocala. He gets them legged up. I just think going to Florida and having those babies ready early is good. It gets them off on the right foot.” Begg also bought another Ontario-bred yearling at the OBS sale this year.
Building his business is at the forefront of Begg’s mind, but his family has also played a pivotal role in his future decision-making.
“In the last year I’ve gotten engaged and I have twins, so with how my lifestyle is coming back home, buying locally just seemed like the better deal. My mom is around to help out. We just bought a house in Tottenham this winter, so I’ve kind of set up roots here.”
While the roots have been planted, Begg will be racking up the miles between Woodbine and the NY tracks in his endeavour to maximize the potential of his current and future roster of runners.
“I’m staying in New York, which is going to line up well, because next year for the winter they are going to bring in the Tapeta. It will actually be a very good winter-summer cycle. You need somewhere to run in the winter, and then obviously in the summer they have Saratoga. I love Woodbine, but there is no better place to win a race than at Saratoga.”
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