Has any jockey ever won the Triple Crown more than once? July 14, 2020September 25, 2011 by Pamela Landy Eddie (“Banana Nose”) Arcaro won the Triple Crown twice, in 1941 on Whirlaway and in 1948 on Citation. Related Answers What three horse races make up the Triple Crown? On what daytime TV drama did New York mayor Edward Koch once appear as himself? In what daytime soap operas did the following movie stars once act: On what daytime TV drama did the rock group the B-52s once perform? Who was the voice of the “Crazy Eddie” stereo stores? Has a woman ever won the U.S. Medal of Honor?