Leyland was the manager of the Pittsburgh Pirates from 1986 to 1996. He won two Manager of the Year trophies with the Pirates in 1990 and 1992, and finished as runner-up in 1988 and 1991. Leyland helped develop such All-Stars as Barry Bonds, Jay Bell, Tim Wakefield, Andy Van Slyke and Bobby Bonilla in Pittsburgh before a fire sale in the mid-1990s soured him with new ownership. Under Leyland, the Pirates captured the National League Eastern Division title and went to the National League Championship Series in three straight seasons (1990, 1991, and 1992). Pittsburgh averaged 96 regular season victories those three years, but lost all three times in the NLCS with the latter two going the full seven games against the Atlanta Braves. The Pirates lost to the Cincinnati Reds (four games to two) in the 1990 NLCS.