In longevity, Bill "Willie" Shoemaker had few rivals. He was still riding mounts in the Kentucky Derby (23 in all) in the 1980s when he was in his fifties, while his chief contemporary, Bill Hartack, had worn out his potential employers with his chronic irascibility and Eddie Arcaro, the great, had wound down his career in the 1960s.
Shoemaker's Derby wins were in 1955, aboard Swaps; in 1959 with Tomy Lee; on Lucky Debonair in 1965; and in 1986 with Ferdinand.
In the 1950s, Shoemaker rode in six other Derbies: 1952 on Count Flame, finishing 5th; 1953, Invigorator, 3rd; 1954, Correlation, 6th; 1956, Terrango, 12th; 1957, Gallant Man, 2nd; 1958, Silky Sullivan, 12th.
The Shoe's other rides in the 1960s included Dr. Miller, 1961, 4th; Candy Spots, 1963, 3rd; Abe's Hope, 1966, 5th; Damascus, 1967, 3rd.
In the 1970s, Shoemaker saddled four Derby hopefuls without getting a win. They were Terlago, 1970, 11th; Agitate, 1974, 3rd; Avatar, 1975, 2nd; and Get the Axe, 1977, 4th.
Shoemaker rode five other times in the Derby in the 1980s. Other than on Ferdinand in 1986, his best 1980s finish was aboard Gulch in 1987 when he came in 6th. In 1981 he rode Cure the Blues to 15th place. Star Gallant placed 7th in 1982. In 1984 he rode to ninth place aboard Silent King. And Lively One took him to a 12th place finish in 1988.
Bill Hartack, who opposed Shoemaker on almost every first Saturday in May of the 1950s and 1960s, won three of his five Derbies within five years. His first Derby victory was aboard Iron Liege in 1957. In 1960 he won with Venetian Way; in 1962 it was Decidedly; in 1964, the great Northern Dancer; and in 1969 Majestic Prince took him first to the wire.
Hartack's other Derby rides included Fabius, 1956, 2nd; Easy Spur, 1959, 13th; Bold Lad, 1965, 10th; George Lewis, 1970, 13th; Warbucks, 1973, 13th; and Sir Tristram, 1974, 11th.
Eddie Arcaro's career spanned four decades. He won his Derbies on Lawrin, 1938; Triple Crown Champion Whirlaway, 1941; Hoop Jr., 1945; Triple Crown Champion Citation, 1948; and Hill Gail, 1952.
Arcaro's Derby finishes in the 1930s included Nellie Flag, 1935, 3rd; and in the 1940s, Devil Diver, 1942, 6th; Stir Up, 1944, 3rd; Lord Boswell, 1946, 4th; Phalanx, 1947, 2nd; and Olympia, 1949, 6th.
In the 1950s Arcaro's other Derby rides were Hill Prince, 1950, 2nd; Battle Morn, 1951, 6th; Correspondent, 1953, 5th; Goyama, 1954, 4th; Nashua, 1955, 2nd; Head Man, 1956, 8th; Bold Ruler, 1957, 4th; Jewel's Reward, 1958, 4th; First Landing, 1959, 3rd.
Arcaro finished his Derby string on Sherluck in 1961. He was fifth behind The Shoe on Dr. Miller.