(As well as having a stable on the rise at Woodbine, trainer Dale Desruisseaux is also a proud family man. He and his wife, Jeannette, are shown with their children Daynica and Dawson – photo courtesy Dale Desruisseaux).
Trainer Dale Desruisseaux can vividly remember feeling a rush when his phone rang and he saw that it was Chiefswood Stable’s general manager Rob Landry calling.
“I was having lunch with a friend and Rob called,” Desruisseaux said. “I said, ‘This is either really good news or there’s some kind of a problem.’”
It was the former.
After repeatedly asking Landry for the chance to train a horse for Chiefswood, Desruisseaux was finally getting his wish.
That horse was Chiefswood’s homebred filly Piper’s Gift. On Saturday (June 6), the 3-year-old Ontario-bred won the $125,000 Fury Stakes at Woodbine for Desruisseaux a day before the trainer also won the $125,000 Queenston Stakes with Ontario-bred Highwaytothemoon at Woodbine.
On Saturday (June 6), Dale Desruisseaux trainee Piper’s Gift (Rafael Hernandez) won the $125,000 Fury Stakes at Woodbine (Michael Burns photo)
Desruisseaux, who turned 40 in January, is coming off a career year in 2025 with earnings of more than $1.1 million. He already has more than $400,000 in the bank in 2026, nearly as much as he earned in all of 2024, which, for now, stands as his second-best season.
After struggling to gain traction for the first 10 years of his career, Desruisseaux said he’s fortunate to have the owners he has now, including Chiefswood, Highwaytothemoon’s owner Dominic DiLalla of Centennial Farms (Niagara) Inc. and Garland and Marie Williamson’s Hillsbrook Farm, owners and breeders of Ontario-bred Dixie Law, another top 3-year-old filly in Desruisseaux’s care.
Piper’s Gift (Yorkton – Piper’s Legacy by Silent Name (JPN)) has a career record of 4-1-0 in seven starts and earnings of $289,639. Dixie Law (Tiz The Law – Bit Of Dixie by Union Rags) is 4-0-0 in six starts for earnings of $289,757. Both fillies are groomed by Kyle MacDonald and both have a shot to race in the Woodbine Oaks.
Highwaytothemoon, a 3-year-old Ransom The Moon gelding out of the Society’s Chaiman mare High Society Gal, is 3-1-1 in six starts and has earnings of $167,453. The gelding was bred by James Everatt, Janeane Everatt and Arika Everatt-Meeuse of St. Thomas, ON and is groomed by Robert Martin.
On Sunday (June 7), Desruisseaux pupil Highwaytothemoon (Rafael Hernandez) won the $125,000 Queenston Stakes at Woodbine (Michael Burns photo).
“We’re very blessed with the clientele that I’m starting to get now,” Desruisseaux said. “They’re providing me with some quality horses. It’s not really anything I’ve changed or done. I’m doing what I’ve been doing all my whole life. It’s just now we’re starting to get the quality stock and we’re able to run in those higher-end races.”
Landry said he knows from his former career as a jockey what it means to get a major opportunity to work for great clients and work with great horses.
“The first 10 years of my career I struggled, but once I got an opportunity and a chance to ride better horses, then all of a sudden, overnight, I could ride,” said Landry, who was inducted into the Canadian Horse Racing Hall of Fame in 2014. “A lot of life is being in the right place at the right time… You need people to give you that leg up sometimes, and then you have to hope that you produce.”
As for why he gave Desruisseaux a shot, Landry said the trainer earned it.
“I’m always watching and seeing how people do things,” Landry said. “I like the way [Desruisseaux’s] barn ran. I like the way he does things. That’s why, when the opportunity arose, I spoke to [Chiefswoods’] owners [Robert and Mark Krembil], and we ended up giving [Desruisseaux] a horse last year, and, apparently, we picked him out a pretty good one.”
Chiefswood, the 2025 Sovereign Award winners as both Outstanding Owners and Outstanding Breeders, now has two horses with Desruisseaux, with a third on its way to the trainer soon.
Desruisseaux said he can’t thank all the owners and his staff enough for the recent success. His 2025 earnings were nearly three times more than his previous best year, and 2026 is shaping up to be similarly successful.
“I wear the hat, my name’s in the program, but these guys are the ones that grind it out every day,” Desruisseaux said of his staff. “I’ve had kind of the same staff for many years, it’s just that, obviously with the [growth], we’ve added some really key pieces. I wouldn’t trade any of my staff for anybody in the backside. I’m really, really blessed, and all my grooms and riders and hot walkers, they’re all great.”
The Smithsville, ON resident said he is also thankful to be having success with Ontario-bred horses.
“Don’t get me wrong, I think every trainer wants to run in the Kentucky Derby, but, the reality is, we’re Canadian, and the King’s Plate, or the Woodbine Oaks are the premier races for us,” Desruisseaux said. “To win those races would be a dream come true, for sure.”
One of many, lately, for the trainer.
As for the moment Chiefswood called, Desruisseaux said he will likely never forget it. Landry said he’s just happy that, so far, it’s worked out well for all involved.
“I am happy for [Desruisseaux],” Landry said. “I am happy that I recommended him, and that Krembils were good with it. I’m also happy with the way things turned out… We’ve got a lot of trainers, and they all do great jobs, but that’s why we’re with them. We wouldn’t be with people if we didn’t have confidence in them.”
These days, Dale Desruisseaux’s confidence is soaring.
