The record for most wins in the Preakness by a trainer is shared jointly by R. Wyndham Walden and Bob Baffert with seven apiece. While Walden dominated the race’s early history, winning the Preakness seven times between 1875 and 1888, Baffert has ruled the middle leg of the Triple Crown in the modern era.
Baffert’s first Preakness Stakes victory came in 1997 with Silver Charm, and he won it again in three of the next five years. It would be another eight years after that until he’d again taste Preakness glory, in 2010 with Lookin At Lucky, and in recent years he’s sent out unquestionably his two most famous Preakness winners, American Pharoah in 2015 and Justify in 2018, both of whom won the Triple Crown.
The following is a list of the most successful trainers of all time and the years they won the race:
R. Wyndham Walden has won the race seven times (1875, 1878, 1879, 1880, 1881, 1882, 1888)
D. Wayne Lukas has won the race six times (1980, 1985, 1994, 1995, 1999, 2013)
Thomas J. Healey has won the race five times (1901, 1922, 1923, 1926, 1929)
Bob Baffert has won the race five times (1997, 1998, 2001, 2002, 2010)
Jim Fitzsimons has won the race four times (1930, 1935, 1955, 1957)
Jimmy Jones has won the race four times (1947, 1948, 1956, 1958)