He was the winner of the 1927 Kentucky Derby after defeating Osmand by a nose in the stretch.
He was third in the 1927 Preakness Stakes and would be named American Champion Three-Year-Old Male Horse that year.
However, he proved to be sterile and was put back into training as a gelding.
Whiskery did not achieve his previous racing success and was finally shipped in 1931 to the Charles Stone's Morven Stud in Charlottesville, Virginia for use as a saddle horse.
[3][4] Whiskery's time of death was not officially reported to The Jockey Club, but it is assumed that he died around 1936 as the result of a catastrophic leg injury, either sustained by colliding with a tree while fulfilling his duty as the night watchman's horse or as a result of a track injury.