Kammala wannan jumla: Leyland ya kasance manajan Pittsburgh Pirates daga 1986 zuwa 1996. Ya lashe kofuna biyu na Manajan Shekara tare da Pirates a 1990 da 1992, kuma ya gama a matsayin na biyu a 1988 da 1991. Leyland ya taimaka wajen haɓaka irin waɗannan All-Stars kamar Barry Bonds, Jay Bell, Tim Wakefield, Andy Van Slyke da Bobby Bonilla a Pittsburgh kafin sayar da wuta a tsakiyar shekarun 1990 ya ba shi sabon mallaka. A karkashin Leyland, Pirates sun kama taken National League Eastern Division kuma sun tafi Wasannin Gasar Wasannin Wasannin Kasa a cikin yanayi uku a jere (1990, 1991, da 1992).
1992) da kuma Pittsburgh ta samu nasarar cin nasara sau 96 a cikin waɗannan shekaru uku, amma ta yi rashin nasara sau uku a cikin NLCS tare da na biyun da suka ci gaba da wasanni bakwai a kan Atlanta Braves. Pirates sun yi rashin nasara ga Cincinnati Reds (wasa hudu zuwa biyu) a cikin 1990 NLCS.