BAILES SURPASSES $20 MILLION IN CAREER PURSE EARNINGS WITH MONDAY DOUBLE AT COLONIAL DOWNS
Posted on July 15th, 2026
NEW KENT, Va. (July 15, 2026) — Veteran Mid-Atlantic trainer Robert Bailes reached a major career milestone Monday at Colonial Downs, surpassing $20 million in career purse earnings after Samotowka Stables’ Gripen captured a $40,000 starter allowance.
The 3-year-old Ontario-bred filly, owned by Samotowka Stables and ridden by Taylor Kingsley, provided the milestone victory.
Bailes reached the $20 million plateau in fitting fashion after opening Monday’s card with another winner, J C’s Boys, to complete a training double.
Through Monday’s races, Bailes has compiled 6,309 career starts with 895 victories and $20,010,840 in purse earnings. His career highlights include a runner-up finish with Scrappy T in the 2005 Preakness Stakes after winning the Grade 3 Withers Stakes.
The milestone follows a career-best 2025 season by purse earnings. Bailes’ stable was highlighted by Next Girl’s victories in the Claiming Crown Glass Slipper Qualifier at Colonial Downs and the Glass Slipper Claiming Crown at Churchill Downs. He also added another Colonial Downs stakes victory when Slam Notion captured the 2025 Star De Naskra Stakes.
“It means a lot,” Bailes said. “Over the past few years, with so many ups and downs and where racing’s been, I didn’t know if I really wanted to stay in it. But these horses have bought me new life. I’ve got nice horses in the barn, and it makes it worth getting up at 3 o’clock every morning. You look forward to doing it.”
The success of Next Girl has Bailes hoping to return to the Claiming Crown later this year, although he is still searching for the right horse.
“I didn’t know if I had anything as strong as I did last year, but it’s definitely something that’s in the back of my mind,” Bailes said. “We’re still looking. There’s time if we find the right horse.”
Bailes said last year’s trip to Churchill Downs wasn’t originally part of the plan but quickly became one of the highlights of his career.
“We had no intention of going out to Churchill and racing, but I’m glad we did,” Bailes said. “Churchill really took care of us, and the owners absolutely loved it.”
He is also evaluating several horses for stakes opportunities during the remainder of the Colonial Downs summer meet.
“We’re looking at a few,” Bailes said. “There’s still a little bit of time, so we’ll see how that plays out.”
The $20 million milestone carries added significance for Bailes, a third-generation horseman whose family has been intertwined with Thoroughbred racing for generations. His grandfather served as the first farm trainer for Christopher Chenery’s famed Meadow Stable, while his father became the first person to saddle Secretariat before the legendary colt launched his Triple Crown campaign.
The Colonial Downs summer meet resumes Thursday with the first of four consecutive racing days. Thursday’s first post has been moved to 10 a.m. ET because of forecasted heat. First post Friday through Sunday remains 12:30 p.m. ET.
