In 1998, all the pieces came together for Cheever when he took the biggest win of his career. He started from 17th position and led 76 of 200 laps to win the 82nd Indianapolis 500, despite sliding in the first turn of the race's first lap, helping bring out the race's first caution period. He was the first owner/driver to win the race since A. J. Foyt (one of Cheever's former bosses) in 1977.