Hall of Famer Eddie Arcaro is the winningest rider in Preakness Stakes history with six victories to his name. Arcaro’s first two winners in the race, Whirlaway in 1941 and Citation in 1948, would both go on to win the Triple Crown. He also won back-to-back editions in 1950 and ‘51 with Hill Prince and Bold, respectively, and won in ‘55 with Nashua and ‘57 with Bold Ruler.
Among more modern riders, Pat Day sits at the head of the pack with five victories, including a string of three consecutive wins in the Preakness from 1994-96.
Only two men have won more than three times but four riders have tasted victory on three occasions.
Eddie Arcaro has those wins (1941, 1948, 1950, 1951, 1955, 1957)
Pat Day's five wins in the span of 11 years shows what a great modern day jockey he is (1985, 1990, 1994, 1995, 1996)
George Barbee, Bill Hartack, Lloyd Hughes and Gary Stevens have all crossed the winning post first three times.