John Stewart isn't your typical horse owner. Honestly, if you walked into a high-end bloodstock sale and saw a guy who looks like he just stepped off a factory floor—because, well, he spent 18 years at Toyota—you might not peg him as the man about to drop $25 million in a single season. But that’s exactly what happened.
In the insular world of Bluegrass breeding and Triple Crown dreams, Stewart has become a human whirlwind. He’s the guy who went from buying his first yearling in 2022 to owning over 230 horses and a 1,000-acre farm in Midway, Kentucky, in what feels like a blink.
People in the industry are still trying to figure him out. Is he a flash in the pan? A billionaire hobbyist? If you look at the data, the answer is a lot more calculated. John Stewart horse racing isn't just a pursuit of trophies; it’s a massive, data-driven bet on the future of the American Thoroughbred.
The Factory Floor to the Winner's Circle
You have to understand where this guy comes from to get why he’s moving so fast. Stewart is the founder of MiddleGround Capital, a private equity firm managing billions. But before the suits and the wire transfers, he was an hourly worker at a Toyota plant.
He basically built his career on "Kaizen"—the Japanese philosophy of continuous improvement. He doesn't just want to win; he wants to optimize. He’s stated repeatedly that he views the racing industry as a "traditionally boring market" that’s ripe for disruption.
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When he launched Resolute Racing, he didn't start with a couple of cheap claimers. He went straight for the juggernaut move. In 2023, he bought the former Shadayid Stud from the estate of the late Sheikh Hamdan bin Rashid Al Maktoum. This wasn't just buying land. It was a statement of intent.
The Resolute Strategy: Turf, Fillies, and Global Ambition
While most American owners are obsessed with the Kentucky Derby and dirt racing, Stewart is zigging where others zag. He’s obsessed with turf.
"Eighty percent of my program is turf," Stewart has said. He’s looking at the global stage—Royal Ascot, the Japan Cup, the European classics. He even bought an interest in Goliath, the German-bred gelding that shocked the world in the King George VI and Queen Elizabeth Stakes.
- The Broodmare focus: He’s buying the best "girls" in the game. He dropped $6 million on Goodnight Olive, a two-time Breeders' Cup champion. He also snatched up Puca, the dam of Derby winner Mage, for $2.9 million.
- The Danzig Connection: Stewart believes the American bloodline has lost too much of its "Danzig" influence—the speed and stamina that made the breed famous. He’s actively buying horses in Australia and Europe to bring those genetics back to Kentucky.
- Technology Over Tradition: He’s building a training center with a replica of the Royal Ascot uphill straight. Who does that? Someone who isn't interested in the "way it's always been done."
What Most People Get Wrong About the Spending
Critics love to point at the checkbook. They see $3 million for an Into Mischief colt or $1 million for a Written Tycoon filly and assume it’s just ego.
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But talk to anyone who knows the MiddleGround Capital playbook. Stewart isn't throwing money; he’s buying assets. He treats his $6 million mares the same way he treats the rescues he saves from feedlots. They get the same hay, the same vets, and the same respect.
He’s also incredibly vocal. In an industry where owners usually hide behind silk curtains and PR firms, Stewart is on social media. He argues with Mike Repole. He invites fans to the Breeders' Cup. He’s trying to kill the "veil" between the elite owners and the people in the grandstands.
Impact on the 2024-2026 Racing Seasons
The results are already showing up in the Equibase charts. In 2024, Resolute Racing pulled in nearly $2 million in North American earnings. By 2025, that number jumped as his private acquisitions started hitting their stride.
He’s already tasted Grade 1 glory with Didia in the New York Stakes and watched Pounce tear up the turf at Gulfstream and Saratoga.
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What’s wild is that he’s just getting started. His homebreds—the ones out of those multi-million dollar mares—are only now reaching racing age. If his theory on genetics and "lean manufacturing" applied to horses holds water, the next two years could see Resolute Racing dominating the stakes calendar.
How to Follow the Resolute Racing Movement
If you're trying to keep up with what Stewart is doing, you have to look beyond the results at Churchill Downs. He is a global player.
- Watch the Turf: Keep an eye on his runners in Australia (trained by Gai Waterhouse) and his European interests.
- The Sales Ring: Follow the Keeneland and Fasig-Tipton auctions. Stewart often sets the market floor for high-end fillies.
- Social Engagement: He’s one of the few owners who actually responds to fans. If you want to know why he bought a certain horse, he might just tell you on X (formerly Twitter).
Stewart isn't just a guy with a fast horse. He’s a guy with a plan to change how the sport works. Whether he succeeds in "fixing" the industry remains to be seen, but he’s certainly making it a lot more interesting to watch.
Next Steps for Fans and Investors:
Check the upcoming entries for Resolute Racing at Gulfstream Park or Fair Grounds. Following Stewart’s trajectory is basically a masterclass in aggressive bloodstock acquisition. If you want to understand the "new money" influence in Kentucky, start by tracking the progeny of his recent $5M+ purchases as they hit the track this spring.