As a boy of 14 Matt Winn saw the first Derby from the back of his father's wagon and dreamed that some day he might run the race himself. Twenty-seven years later he was general manager of Churchill Downs, brought it to new eminence and never missed a Derby until he died in 1949.
Vagrant won the second Derby and continued to race until he was 10; yet his reward on retirement was to pull a cart through the streets of Lexington.
Bookmakers were allowed at Churchill Downs for the first time, and they made Runnymeade a 4-to-5 favorite with no place betting. Apollo, at 10 to 1, won, and Runnymeade ran second.
Jockey Billy Donohue bet his life savings on his mount, Leonatus, and won easily. Donohue was a good judge of horses, apparently, for Leonatus never again lost a race.
In the slowest Derby ever run, all four jockeys were told to hold back for a mile, and the Negro rider Isaac Murphy pulled away in the last half mile to win his third Derby.
Only three starters went to the post, and Huron raced to a six-length lead, to be beaten a nose on the post by Azra.
A local sheriff threatened to destroy the Derby if bookmakers were permitted on the course, so Matt Winn, bless him, found a statute that allowed parimutuel betting.
Regret, the only one of 28 fillies to start in history of race to date, won her Derby handily.
Man o' War didn't make his Derby because his owner thought a mile and a quarter in May was too far for a 3-year-old to run, thus depriving the "mostest hoss" of the "mostest race."
Sunny Jim Fitzsimmons urged Earle Sande out of retirement to handle Gallant Fox, giving Sande his third winner. Upon seeing Sande cross the finish line, Damon Runyon wrote: "Roll back the years! Yea, roll 'em!/ Say, but I'm young agin,/ Watchin' that handy/Guy named Sande,/Bootin' a winner in !"