The history of horse racing is filled with stories of improbable, against-the-odds triumphs and legendary heroes who made the seemingly impossible, possible.

Nowadays, it’s difficult to imagine that the Kentucky Derby – as iconic a sporting event as you’ll find – was once in danger of fading into history due to financial difficulties. Fortunately, a businessman and racing fan named Martin Joseph Winn, better known as “Col. Matt Winn,” was determined to keep the Derby alive. More than a century later, it’s not a stretch to say that Matt Winn saved the Kentucky Derby and made it what it is today.

In retrospect, there very likely was no person better-suited than Winn to embrace the challenge of resurrecting Churchill Downs and the Derby. Born on June 30, 1861 in Louisville, Ky. – home of Churchill Downs – the young Winn was in attendance when the first Derby was held in 1875. Throughout the remainder of the century, he continued to attend the Derby while working a variety of jobs, including a stint as a traveling salesman and, eventually, a longer-term job as a tailor.

James Butler with Matt Winn (George D. Widener Collection/BloodHorse Library)

But by the end of 1902, Churchill Downs and the Derby were in danger of disappearing from the sport. By some accounts, the track was suffering severe financial difficulties, and even the Derby itself seemed to be losing some of its luster – only four horses turned out to contest the 1902 Kentucky Derby, one year after a field of five had faced the starter for the 1901 renewal.

According to Winn’s autobiography “Down the Stretch: The Story of Colonel Matt J. Winn,” he was approached in 1902 by his friend, Churchill Downs secretary Charlie Price, with news that the track needed help and could be purchased for $40,000. Aside from being a racing fan, Winn had no experience in the sport and wasn’t terribly enthusiastic about jumping in on the business end, but with the Derby at stake he couldn’t turn away. Winn told Price, “I’d say no and make it stick for a thousand years if it involved anything but the Derby. But they mustn’t stop running that race.”

Thus, Winn joined a partnership that purchased Churchill Downs and set about renovating the facility. Officially, Winn became vice president and general manager of Churchill Downs, though unofficially, it could be argued that Winn was still a salesman – only now, he was selling something intangible; he was selling the Derby as an experience, a can’t-miss sporting event unlike any other.

Winn pulled out all the stops to help the Derby grow from a regional event to a race of national stature. He knew that publicity and press could go a long way to help the race gain traction, so he tried to be accommodating to those in the position to promote the Derby. In the book “The Kentucky Derby: How the Run for the Roses Became America’s Premier Sporting Event,” author James C. Nicholson writes of Winn’s “friendly relationship with members of the press. Winn spent much of his winter ‘off season’ in New York at the Waldorf-Astoria [Hotel], where he often entertained sportswriters and picked up their tabs. He encouraged top sports journalists to come to the Derby, and made sure they were well treated while in Louisville.”

Winn’s courtesy also extended to prominent Thoroughbred owners based in New York, the epicenter of top-quality racing in the United States at the time. A particularly significant moment occurred when the socially prominent Harry Payne Whitney agreed to send his unbeaten filly Regret to contest the 1915 Kentucky Derby; according to the book “Horse Racing’s Top 100 Moments,” published by BloodHorse Publications, “Winn went so far as sending a letter to Algernon Daingerfield of The Jockey Club in New York City imploring him to persuade Regret’s owner to include the Whitney horses in the Kentucky Derby ... ”

Matt Winn (BloodHorse Library)

In a historic moment, Regret won the Derby in decisive fashion, becoming the first filly to prevail in the race. The Daily Racing Form of May 9, 1915, quoted Whitney as saying, “I do not care if she never wins another race, nor if she never starts in another race, she has won the greatest race in America and I am satisfied.”

Suddenly, the Kentucky Derby was on the rise again.

But for all of his forward-thinking ideas and promotions, arguably Winn’s greatest contribution to the Kentucky Derby – and the entire sport – was a last-minute change to the form of wagering offered at Churchill Downs, a move driven by desperation during the early years of Winn’s career at the track. In 1908, bookmaking was outlawed in Kentucky, a move that threatened the ability of Churchill Downs to generate purse money for their races. Without wagering, Churchill Downs and the Derby could not survive.

Fortunately, the quick-thinking Winn remembered an occasion three decades earlier when the track had experimented with pari-mutuel wagering run by machines, allowing racing fans to bet among themselves while leaving bookmakers out of the equation. After discovering an obscure statute that exempted the pari-mutuel machines from Kentucky’s anti-gambling laws, Winn orchestrated a cross-country search to find machines that could serve at Churchill Downs on the day of the rapidly approaching 1908 Derby. Amazingly, six machines were found, and the Derby went off as scheduled, with longshot Stone Street prevailing and paying $123.60 for every $5 win bet, the minimum at the time.

From that point on, the Derby grew quickly in prestige. Huge crowds turned out every year, and the purse of the race climbed from $6,000 in 1912 to more than $50,000 by 1921, the same year that Winn introduced the tradition of awarding a valuable gold cup to the winner. Horses came from all over to compete in the race; Triple Crown winners Sir Barton, Gallant Fox, and Omaha all stamped their legacies with Kentucky Derby victories. Travel restrictions during World War II threatened the Derby, but Winn managed to keep the race afloat, even holding the race a month later than usual in 1945 to ensure that its uninterrupted history continued. Radio and television broadcasts of the race were also implemented during Winn’s tenure at the track.

Fittingly, Winn lived to the age of 88, just long enough to witness his 75th consecutive Kentucky Derby. Without his efforts, it’s unlikely that the race would have ever survived to that milestone; now, the race in 2024 will be twice that old and continues to break wagering and attendance records with regularity.

We can thank Matt Winn for saving the run for the roses.

Note: This story was originally published in 2017 and has been updated.

Fun Facts

• In 2017, Matt Winn was inducted into the Racing Hall of Fame as a “Pillar of the Turf.”
• Winn’s memory is honored each year with the running of the Grade 3 Matt Winn Stakes at Churchill Downs.
• Winn is widely credited with convincing owner Willis Kilmer to run longshot Exterminator in the 1918 Kentucky Derby, a fortunate turn of events since Exterminator won the race convincingly on his way to becoming one of the sport’s most legendary racehorses.
• The tradition of playing “My Old Kentucky Home” prior to the Kentucky Derby was started by Winn.
• Winn was a member of the Royal Order of Kentucky Colonels, hence the “Colonel” title that usually preceded his name.