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

It’s hard 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 Colonel 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.

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.

It was then that 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 the head of Marketing. 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.

Winn spent much of his winter off season in New York at the Waldorf-Astoria, 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.

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.

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.

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 is nearly twice that old and continues to break wagering and attendance records with regularity.

Thank you Matt Winn for saving the Run For The Roses.