Willie Shoemaker

As the only jockey to win two Triple Crowns, Eddie Arcaro is one of the finest riders in racing history. He began riding thoroughbreds at age fourteen and entered his first race in 1931. Arcaro's career took off after his contract was sold to Calumet Farms, which provided his first Derby winner, Larwin, in 1938. He would become known as a strong, instinctual rider who credited his horses in his wins and earned himself the nickname "The Master."

Arcaro had seventeen wins in the legs of the Triple Crown—the Kentucky Derby, Belmont Stakes, and Preakness—including a tie with Bill Hartack for a record five Derby victories. He captured all three in one year for the first time in 1941 with Whirlaway, and then again in 1948 on Citation. When Arcaro rode Nashua in the Derby in 1955, the now senior rider placed second behind Shoemaker on Swaps. A rivalry was made despite the fact that Swaps would not appear in the subsequent Belmont or Preakness, both of which Arcaro would win on Nashua, so a special $100,000 match race was held. In this competition, Arcaro won easily.

The horse that Arcaro admired most was Kelso, with whom he paired to win twelve out of fourteen races at the end of his career. He retired at age forty-five in 1961. His record 554 stakes wins would stand until Shoemaker passed this mark in 1972. After he retired from racing, Arcaro worked as a sportscaster on radio and television. He died at age eighty-one in 1997.