Who Was the Greatest Jockey?

Eddie Arcaro, Bill Hartack, and "Willie" Shoemaker topped the Sport of Kings beginning in the 1930s, through the 1980s, as sought after jockeys. Who was the best?

Who was the best jockey of all time? Eddie Arcaro won five Kentucky Derbies, matched only by Bill Hartack's five victories in the Run for the Roses. Bill "Willie" Shoemaker won four Derbies.

In a different era of Thoroughbred racing, Arcaro, Hartack, and Bill "Willie" ruled the roost as the top jockeys of the Sport of Kings. Over several different decades they battled with each other. From the 1930s, beginning with Arcaro, through the 1980s, ending with Shoemaker, their names showed up over and over again in the Kentucky Derby lineups.

I was about seven when I began to watch and to read up on Thoroughbred racing, so I can remember the earlier years of Hartack and Shoemaker. Arcaro's beginnings I learned about second hand from the library. (Yes, this was before cable stations and Sports Center.)

On the surface, the answer to our who is the best question would seem to be Arcaro. He rode two (of eleven all time)Triple Crown champions in Whirlaway (1941) and Citation (1948). No other jockey - ever - has done that. Unreal!

But, if we count longevity, I can make a real good case for my man, The Shoe, as he was called. Willie Bill won his first Kentucky Derby in 1955 on Swaps, beating Arcaro on Nashua. Thirty-one years later, in 1986, Willie rode Ferdinand to the Derby winner's circle, his last Derby victory, but not his last Derby ride.

Throughout the 1980s, owners and trainers still went to The Shoe to ride their Derby hopefuls. He rode in 1981, '82, '84, '86, '87, and '88 while in his fifties. He won a total of 8,833 races, to Arcaro's 4,779, and Hartack's 4,272.

Gotta go with The Shoe.