The tailor, the filly, and the gamble that created the modern Kentucky Derby

Matt Winn’s Rescue of the Failing Kentucky Derby

The Kentucky Derby was almost lost to history until a tailor stepped in.

Matt Winn first saw the race as a 13-year-old boy in 1875, then saved it from ruin in 1902 when he bought the bankrupt Churchill Downs for $40,000.

Soon after, he faced a crisis when betting laws changed, so he rushed to find old French gambling machines that kept the races legal.

Winn then cut bet costs from $5 to $2, letting working folks join the fun for the first time. He even got a famous filly named Regret to race in 1915, which put the Derby in newspapers across America.

The Derby Museum now showcases how this one man turned a failing local race into America’s greatest sporting tradition.

A Teenage Boy Witnessed Racing History That Would Shape His Life

Matt Winn watched the first Kentucky Derby in 1875 as a 13-year-old boy, sitting on his dad’s wagon near Churchill Downs.

Born in Louisville in 1861, he fell in love with horse racing that day and never missed a Derby afterward. He sold goods on the road before opening a tailor shop in Louisville.

His childhood love for the Derby stuck with him for decades, planting seeds for his future business choices.

The Once-Proud Track Faced Complete Financial Collapse

By 1902, Churchill Downs nearly went bankrupt, with the Kentucky Derby close to ending forever. The race lost its appeal, drawing just four horses that year, down from five in 1901.

The track struggled with money problems for years, hurt by horsemen boycotts over gambling disputes.

One of Winn’s tailor shop customers, William Applegate, asked him to join a group buying the failing track for $40,000 before it closed for good.

A Tailor With No Racing Experience Said Yes To Save The Derby

Winn wasn’t sure about helping save Churchill Downs. He knew nothing about running a racetrack beyond being a fan.

He told his friend Charlie Price he would say no to such an offer “for a thousand years if it involved anything but the Derby. ” His love for the race won out.

He led a group that bought Churchill Downs for $40,000 in 1902, becoming vice president and general manager. He quickly spent $20,000 fixing the clubhouse.

The Track Made Its First Profit After Decades Of Losses

Churchill Downs earned its first yearly profit in 1903 with Winn in charge. He fixed the grounds to attract better horses and bigger crowds to Louisville.

He sold the Derby as a complete experience rather than just another horse race.

Winn reached out to rich horse owners and newspaper writers from New York and other eastern cities, trying to grow the Derby beyond its small regional status.

City Officials Almost Killed Racing With Anti-Gambling Laws

In 1908, Louisville leaders started enforcing laws against bookmaking that put Churchill Downs in danger. The track needed money from betting fees to pay for race purses.

A nationwide reform movement wanted to stop all types of gambling across America. Without money from wagering, both the track and Derby faced shutdown, threatening everything Winn had built.

French Machines Arrived Just In Time To Save The Day

Winn remembered that pari-mutuel machines had been tried at Churchill Downs years earlier. He found an old Kentucky law that said pari-mutuel betting wasn’t covered by anti-gambling rules.

He sent people across the country to find old French betting machines from New York and Paris. Workers rushed to fix the equipment barely in time for the 1908 Derby, giving fans a legal way to bet on races.

Mud-Splattered Longshot Proved The New Betting System Worked

Stone Street won the 1908 Derby running through deep mud, finishing with the slowest time ever at 2:15. 20.

Even with rain pouring down, curious crowds showed up to try the new pari-mutuel betting system. A $5 bet on Stone Street at 24-1 odds paid $123.60, creating buzz around the track. The new wagering approach kept Kentucky racing alive when it seemed doomed.

The Two-Dollar Bet Brought Working People To The Races

Winn cut the minimum bet from $5 to $2 in 1911. This simple change opened Derby betting to regular working people for the first time.

He also noticed women’s growing buying power and made Churchill Downs more welcoming to female visitors.

By combining cheaper betting with celebrity marketing, he broadened who came to the Derby and who cared about its outcome.

A Filly Named Regret Turned The Derby Into A National Event

Winn talked rich New York horse owner Harry Payne Whitney into sending his unbeaten filly Regret to run in the 1915 Derby. Regret became the first female horse to win the Kentucky Derby, beating 15 male horses easily.

Whitney told reporters afterward that the Derby was “the greatest race in America,” giving Winn a perfect endorsement.

Newspapers across the country covered Regret’s historic win, helping make the Derby a major American sporting event.

A Song And Roses Created Lasting Derby Traditions

Winn started playing “My Old Kentucky Home” before the race in the early 1920s, creating an emotional connection with fans. He introduced a solid gold trophy in 1924 to make winning the Derby more prestigious.

The famous garland of roses became official in 1932, building on earlier traditions of draping the winner with flowers.

Winn created the first collectible mint julep glass in 1939, adding another souvenir fans could take home from their Derby experience.

The Man Who Never Missed A Derby Left A Permanent Mark

Winn served as Churchill Downs president and general manager for 47 years until he died in 1949. The New York Times wrote that “He alone made it what it is today.”

He stood firm when the government asked him to cancel the 1943 Derby during World War II, insisting the race must go on.

Today, Churchill Downs honors him with the Matt Winn Stakes race, a restaurant bearing his name, and a bronze statue overlooking the paddock where Derby winners are saddled.

Visiting Kentucky Derby Museum, Kentucky

The Kentucky Derby Museum at 704 Central Avenue in Louisville tells Matt Winn’s story of saving Churchill Downs from bankruptcy in 1902.

Your general admission ticket gets you a 30-minute guided walking tour of the racetrack, plus “The Greatest Race” 360-degree film and two floors of interactive exhibits.

The museum is open 8am-5pm Monday-Saturday and 11am-5pm Sunday. You can also book premium tours like Backside Training or Bourbon & Bridles experiences.

This article was created with AI assistance and human editing.

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