John Stewart’s journey from a Toyota line worker to a private equity tycoon with an eye for high-stakes horse racing endeavors is one of metamorphosis and calculated investment. Stewart, a native of Kentucky, rose to prominence in the thoroughbred racing industry thanks to his enduring love of horses and business savvy. His investments in horse racing and private equity ventures have made substantial contributions to his current net worth of about $1 billion.
It was not Stewart’s original plan to enter the horse racing business. He worked for Toyota for eighteen years, moving up from line worker to executive positions, before changing careers and going into private equity in 2007. Stewart was a co-founder of MiddleGround Capital in 2018, an asset management company that expanded quickly to oversee more than $3.5 billion by 2024. But his entrepreneurial spirit was not satiated by his success in private equity. This prompted him to put money into horse racing, a field that was near and dear to his heart.
John Stewart’s Horse Racing Ventures and Net Worth
| Attribute | Details |
|---|---|
| Full Name | John Stewart |
| Date of Birth | 1969 |
| Age | 55 years |
| Place of Birth | Jamestown, Kentucky, USA |
| Nationality | American |
| Profession | Private Equity Investor, Horse Racing Owner, Entrepreneur |
| Net Worth | $1 Billion |
| Key Business Ventures | Founder of MiddleGround Capital, Owner of Resolute Racing |
| Investments in Racing | $25 Million Spent on Horse Bloodstock, $1.1 Million Earned in Racehorse Partnerships |
| Major Purchases | Goodnight Olive ($6 million), Pizza Bianca ($3 million), SheDaresTheDevil ($2.5 million) |
| Industry Influence | Active in Thoroughbred Racing, Renowned Investor, Entrepreneurial Leader |
He made a dramatic debut in racing. At the Keeneland September Yearling Sale in 2022, Stewart paid $235,000 for his first horse, Shiloh’s Mistress. Stewart’s subsequent $25 million expenditure on thoroughbreds, which shocked many in the industry, demonstrated his serious interest in the sport. His newfound passion for racing led him to establish Resolute Racing, a 1,000-acre thoroughbred breeding and racing facility located in Midway, Kentucky. In keeping with the long tradition of bloodlines that have made Kentucky the center of American horse racing, the facility seeks to breed and train champion horses.
Stewart approaches horse racing with a strategic fusion of business acumen and passion. Stewart approaches the sport like any other business endeavor, using his experience in private equity to make data-driven decisions, unlike many investors who merely buy horses in the hopes of making a significant profit. This methodical approach is reflected in his investments in Resolute Racing. The success of Stewart’s hands-on but strategic approach to the industry is demonstrated by the millions his firm has made through racehorse partnerships and winnings in just a few years.
Stewart has made some very audacious purchasing choices. He bought Pizza Bianca for $3 million, added SheDaresTheDevil to his stables for $2.5 million, and spent $6 million on the racehorse Goodnight Olive. These acquisitions are investments in the future of his racing empire rather than merely buying horses. Stewart further cemented his position as a prominent figure in horse racing by spending an additional $6 million on nine yearlings at the Magic Millions auction. His readiness to spend large sums of money on superior horses shows that he is dedicated to building a racing team that can contend at the greatest levels.
Stewart has used his background in private equity to oversee a variety of assets in addition to his racing empire. He owns stakes in more than 180 factories worldwide through his industrial manufacturing-focused company, MiddleGround Capital. Stewart has been able to effectively manage risk thanks to his diverse investment portfolio, with the profits from his various endeavors supporting his high-stakes horse racing investments.
His ability to diversify into several luxury industries adds to his net worth. Stewart is well-known for his real estate, fine art, and luxury car collections in addition to his horse racing activities. His financial success has been largely attributed to this wealth management strategy, which strikes a balance between high-risk endeavors and safe, valuable assets.
Despite his achievements, Stewart has encountered legal issues, especially those pertaining to MiddleGround Capital, his private equity firm. Stewart and MiddleGround were sued for $22 million in 2024, claiming that the company had not fulfilled its end of the bargain. Stewart, however, refused to back down, claiming that the lawsuit was an attempt to coerce the company into making an unjust agreement. Stewart remained committed to expanding his horse racing business and making sure Resolute Racing remained successful as the case approached settlement in early 2025.
Stewart’s love for the game has not diminished despite his legal troubles. Instead, they appear to have strengthened his dedication to the racing world. His long-term vision for the sport is evident in his continued investments in top-notch horses and his dedication to turning Resolute Racing into a world-class breeding and training facility. His desire to succeed and rule in a field that rewards the brave is reflected in his aggressive approach to purchasing yearlings and stocking his stable with elite horses.
John Stewart’s rise to prominence in horse racing is a result of a larger trend in which private equity investors are becoming more interested in the sport. Stewart sees horse racing as a high-reward endeavor that combines the excitement of competition with the astute investor’s strategic thinking.
Stewart’s net worth is probably going to increase even more as he builds his reputation in the horse racing sector. He is one of the most important people in racing today because of his ability to spot and develop racing talent as well as his extensive knowledge of finance. Resolute Racing appears to have a bright future, and Stewart’s success in racing is virtually guaranteed given his history of success in a variety of industries.
