Oliver was born in the year 1856, on Fayette County, Kentucky, to peasant parents, Goodson and Eleanor Lewis.
Along the line, he was also blessed with siblings named Isaac E. Lewis and George Garrett Lewis, all on Fayette County.
Oliver was just a nineteen year old when he was tucked into his first ever Kentucky jockey race; it was held at what was known as the Louisville Jockey Club.
About a ten thousand spectators watched this race, at a time whereby the horses were given names for identification.
Moreover, Oliver Lewis was not, actually, a part of the race, but he was instructed to lead the race and tire out the other horses, so that attention will not be on William Henry’s horse Chesapeake; this was a stunt pulled so that this horse could win the $2,850 prize.
Unfortunately, the special horse couldn’t make it to the finish line while Lewis and his horse, Aristide, managed to win by crossing the finish line, winning by two lengths.
This was not the last to be heard of Lewis; he came second in another jockey race in the New York’s Belmont Stakes and won three other races at the Louisville Jockey Club, with the same horse named Aristide.
Oliver Lewis gave up the ghost at sixty-eight years of age in the year 1924, after a life well lived through sports.
Currently, the Louisville Jockey Club is known as the Churchill Downs in Kentucky.