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As a teenager in 1875, Matt Winn saw the race from an infield seat on his father’s grocery wagon. In 1886 he bought his first pari-mutual ticket and won. By the early 1890s Churchill Downs was in financial trouble. A full house on Derby Day could not support the rest of the year. After the Spring Meet in 1902, Churchill Downs on its last legs was purchased by Winn and others. They raised $20,000 and the next Spring Meet was the first profitable in meet in Down’s history. A year later Winn a devoted father of a large family took his biggest risk and became the GM of Churchill Downs. Such was his ethics, that from that day on he never placed a bet again. Racing became his life. He made Churchill Downs a community landmark with concerts and fairs and even grew potatoes in the infield during WW I. Winn commissioned the unique Gold Cup trophy for the winners in 1924 and welcomed technical innovation and the media who made the Derby “the greatest two minutes in sports”. Winn passed away in the fall of 1949 capping a lifetime of devotion to his family, his home and his beloved race.