Despite a second-place finish in the Norfolk Stakes at Santa Anita in late September, Darley Stable privately purchased Midshipman from Stonerside Stable, and the son of Unbridled’s Song paid quick dividends by winning the 2008 Breeders’ Cup Juvenile less than a month later. Among his victims that afternoon at Santa Anita was future Kentucky Derby winner Mine That Bird, who finished last of 12 in the field. Midshipman dueled with lukewarm favorite Square Eddie before finally shaking that one off and pulling away to a1 1/4-length score. He covered the 1 1/16 miles in 1:40.95 under Garrett Gomez as the $3.60-1 second choice in the field of 12 for trainer Bob Baffert.
Midshipman would go on to win the Eclipse Award as top 2-Year-old Male, but a soft tissue injury kept him out of the Triple Crown the following spring. He recovered to finish third in the Breeders’ Cup Dirt Mile the next fall before eventually being retired to stud by Darley in 2010 with five wins from eight career starts.