The Preakness Stakes has long been a proving ground for the toughest and most talented 3-year-olds each year. Run two weeks after the Kentucky Derby, colts have traditionally dominated this middle jewel of the Triple Crown, but its 150-year history has seen a few fillies rise to the challenge and etch their names into history.

Real Quiet did not look or act the part of a champion early in his career. He was so crooked up front that he sold to Michael Pegram for only $17,000 as a yearling in 1996. He was so lacking in girth that his trainer, Bob Baffert, jokingly nicknamed him “The Fish.”