Menifee won a come-from-behind victory in the Blue Grass Stakes at Keeneland in his last Triple Crown prep over the highly regarded Cat Thief, Vicar, Kimberlite Pipe and Wondertross.
Two weeks later, in the 1999 Preakness Stakes, he garnered a great deal of support, being sent off as the morning line favorite at 2–1 in a full field of 13 colts and 1 filly (Silverbulletday).
In the race, Cat Thief and Vicar took the lead early while Menifee settled into mid-pack at eighth and Charismatic lagged behind in tenth.
Following the Triple Crown series in the summer of 1999, Menifee won the Grade I Haskell Invitational Handicap at Monmouth Park Racetrack, finished second in the Super Derby, and ran third in the Travers Stakes.
In October 2006, it was announced that he had been sold to the Korean Racing Association to continue his stallion career at Jeju Stud Farm.