In the storied history of Churchill Downs, there has never been a leader that was both as innovative and colorful as the legendary Colonel Matt J. Winn. Although his arrival at the Downs was 100 years ago, his impact serves as an indelible signature that he left on Churchill and the famed Kentucky Derby.

In his final year as Churchill Downs president, the 1949 Diamond Jubilee Kentucky Derby souvenir glass featured a picture of Matt Winn with the legend “He has seen them all!.” The glass was a fitting tribute to Winn, the Kentucky Derby’s tireless promoter, who made the race his lifelong passion.

It began with the first running of the Derby in 1875. As a teenager, Winn watched the event from an infield seat on his father’s grocery wagon. Winn’s excitement and thrill of the Derby grew deeper as he bought his first pari-mutuel ticket and won in 1886. Winn was a skilled handicapper and he never forgot the experience of being a fan and winning a race.

By the early 1890s Churchill Downs was in financial trouble. A full house on Derby Day did not support the track all year long. In 1894, it was sold to a group of investors who spent $100,000 to build a new grandstand, topped by twin spires on the north side of the track.

In spite of the improvements, by 1902 Churchill Downs was on its last legs. Derby fields were small due to the depressed economy and a boycott by eastern racing interests.

Winn, meanwhile, was a successful middle-aged businessman and a partner in a men’s custom clothing store where he developed a national clientele as a sales representative. His motto, and his lifelong advice to others on how to succeed, he could put in three words: “Always be polite.”

After the 1902 Spring Meet, Charlie Price, Winn’s friend and Churchill Downs Secretary, begged him to buy the operation. Without new management, the track was dead. Winn called friends, among them hotelman Louis Seelbach and Louisville Mayor Charles Grainger, and formed a new corporation to save the Derby.

By early 1903 they had sold 200 “Jockey Club” memberships at $100 each. A new $20,000 clubhouse was built with that money for the Spring Meet, the first profitable meet in Downs’ history.

A year later, Winn, a devoted father of a large family, took the biggest risk of his life. He sold his business and was named Vice President and General Manager of Churchill Downs. Due to his sense of ethics, from that day on he never placed another bet. Racing became his life.

In a decade-long struggle, he faced and outwitted the Downs’ biggest rival, nearby Douglas Park, in the “turf wars.” When Louisville barred bookmakers from operating within the city limits in 1908, Winn resurrected the long-abandoned pari-mutuel machines for the tack’s wagering patrons.

During the pre-war years when “reform” movements shut down tracks nationwide, Winn opened tracks in Mexico to keep racing alive. He made Churchill Downs a community landmark with concerts and fairs in the infield, where he also grew potatoes during World War I.

In 1919, Winn formed the Kentucky Jockey Club as a holding company for Churchill and three other Kentucky tracks: Latonia, the Kentucky Association in Lexington and Douglas Park, also in Louisville. Over the next 10 years the operation grew to include Fairmount Park in East St. Louis, Ill. And Lincoln Fields in Crete, Ill.

The Kentucky Jockey Club reorganized with the creation of the American Turf Association in 1928. The Association served as a holding company for the various tracks and also included Washington Park in Illinois that was purchased that year. Although the American Turf Association was later disbanded, Winn is credited with the creation of the most powerful racing organization of the period.

Winn created several of the Kentucky Derby traditions that have become synonymous with the event. The playing of “My Old Kentucky Home,” the intricate garland of roses presented the winner and even the Kentucky Derby glasses were developed by Winn. For the Kentucky Derby’s 50th anniversary in 1924, he commissioned a unique gold cup to be presented to the winner. One just like it has been presented each year since that time.

Under his guidance the Derby continued, uninterrupted by the Great Depression and World War II, during which time he set up Camp Winn in the infield. In 1945, the Derby was postponed until June 9, but it was run. No war was going to stop Winn. His visionary focus made the Derby “The greatest two minutes in sports.”

Winn’s death in the fall of 1949 capped a lifetime of devotion to his family, his home and his beloved race.