Matt Winn

He was asked by one of his clients, William E. Applegate, (who, at that time, owned over eighty percent of the New Louisville Jockey Club) to become involved in the reorganization and management of Churchill Downs.

Winn came on board as vice president to run the catering operation and summer entertainment and in 1914 he was listed as general manager of the new Louisville Jockey Club.

[3] A skilled marketer, in his first year running the racetrack, his promotions for the event saw the business make its first-ever annual profit.

In 1915, he convinced the multimillionaire sportsman Harry Payne Whitney to ship his highly rated filly Regret from New Jersey to Louisville to compete in the Derby.

Whitney agreed, and Winn's effort paid off with nationwide publicity surrounding the first filly to ever win the Derby.

Matt Winn's picture appeared on the official 1949 Kentucky Derby Mint Julep Glass with the caption "He Has Seen Them All." He had seen every derby run, since the first derby in 1875, when he was 14 years old.