There have been many great horses to win the Kentucky Derby and many arguments over who is the best. This list uses the criteria of most year end honors won in their 3-year-old season to select the best horses to ever win the Kentucky Derby. Only those who were both 3-year-old champion and Horse of the Year as well as the Derby winner are included and they are presented in chronological order.
War Admiral was the fourth horse to sweep the Triple Crown and he won his Kentucky Derby by 8 lengths. He went on to be champion 3-year-old colt and Horse of the Year for 1937 with 8 wins in 8 starts that year. He may be best remembered for his famous match race with Seabiscuit in 1938 where he lost. His lifetime record was 26 starts with 21 wins, 3 seconds, and 1 third with $273,240 in earnings.
Calumet Farm's Whirlaway kept a busy schedule during his racing career and raced until he was 5-years-old. He was known to be erratic and have a tendency to bolt, so he wore special blinkers to try and correct that. He was named 3-year-old champion and Horse of the Year in 1941 and also champion handicap horse and Horse of the Year in 1942. In his career he started 60 times with 32 wins, 15 seconds, and 9 thirds with $561,161 in earnings.
Count Fleet only raced at age 2 and 3, but was never out of the money, with 21 starts, 16 wins, 4 seconds, and a third with earnings of $250,300. He won all three of his Triple Crown races easily, the Derby by 3 lengths, the Preakness by 8, and the Belmont by 25. He was named champion 2-year-old for 1942, and champion 3-year-old and Horse of the Year for 1943.
Citation is often brought up as a top candidate in any argument over the best thoroughbred of all time. Only out of the money once in 44 starts lifetime, he won multiple championships including: champion 2-year-old colt of 1947, champion 3-year-old colt of 1948, champion Handicap Horse of 1948, and Horse of the Year for 1948. He still holds the record for most stakes wins in a year, 17 in 1948. He started 45 times with 32 wins, 10 seconds, and 2 thirds with $1,085,760 in lifetime earnings.
Secretariat was the next horse to win the Triple Crown after Citation, breaking a 25 year drought. He is one of the few horses to win Horse of the Year honors at age 2 and the only to repeat it at age 3. He was also named champion 2-year-old for 1972, champion 3-year-old for 1973, and champion Grass Horse for 1973. He still holds the track record for both the Kentucky Derby and Belmont Stakes. He retired with a lifetime record of 21 starts, 16 wins, 3 seconds, 1 third, and $1,316,808 in earnings.
Seattle Slew was a champion at ages 2, 3, and 4 winning champion 2-year-old colt for 1976, champion 3-year-old colt for 1977, champion older horse for 1978, and Horse of the Year for 1977. He was undefeated at age 2 and remained undefeated all the way through the Belmont Stakes. His lifetime record was 17 starts, 14 wins, 2 second, no thirds, and $1,208,726 in earnings. After he retired, he stood at stud at Three Chimneys Farm and sired many stakes winners including Slew o'Gold, Swale, and Landaluce.
Affirmed in 1978 was the last horse to win the Triple Crown. He had a frequent rivalry with Alydar who ran second to him in all three Triple Crown races. He won championships each year he raced, being named champion 2-year-old colt for 1977, champion 3-year-old colt for 1978, champion older horse for 1979, and Horse of the Year in both 1978 and 1979. He retired with a record of 29 starts, 22 wins, 5 seconds, and 1 third with $2,393,818 in earnings.
Sunday Silence was never worse than second in his 14 lifetime starts, with 9 wins and $4,968,554 in earnings. He is often remembered for his rivalry with Easy Goer who stopped him from being a Triple Crown winner by beating him in the Belmont Stakes, although Sunday Silence won their other 3 meetings including the Breeders' Cup Classic. He was named champion 3-year-old colt for 1989 and Horse of the Year for 1989. He was injured early in his 4-year-old season and retired to stud in Japan where he became one of their best sires ever. He died in 2002 after a long battle with laminitis.
Charismatic was a long shot winner of the Kentucky Derby, but he still went on to win the Preakness and was 3rd in the Belmont where he broke his leg after the finish. Jockey Chris Antley pulled him up and kept the leg off the ground until the vet arrived. He had surgery the next day to repair the leg and is currently standing at stud in Japan at Iburi Stallion Station. His final career record was 17 starts, 5 wins, 2 seconds, and 4 thirds with $2,038,064 in earnings. He was named champion 3-year-old colt and Horse of the Year for 1999.