In 1997, he was hired by Wayne Huizenga, to manage the Florida Marlins. Leyland led the team to their first championship later that same year. In the offseason, Huizenga dismantled the team in what became known as "the fire sale." Leyland remained as the manager, but resigned after the the disasterous 1998 season. At his press conference, Leyland remarked that his thought his job was to win championships, but that apparently wasn't what Huizenga wanted. Leyland was subsequently hired by the Colorado Rockies for 1999 season..
His career managerial record is 1069-1131, a .486 winning percentage. He led the Pirates to three straight division titles from 1990-1992. He won two Manager of the Year Awards with the Pirates in 1990 and 1992. When he left managing after the 1999 season, he became a Pittsburgh-based scout for the St. Louis Cardinals; he can often be seen sitting in the stands at PNC Park with fellow ex-Pirates manager Chuck Tanner.
Following the release of Alan Trammell as the manager of the Detroit Tigers on October 3, 2005, Leyland was immediately named a top contendor to replace him for the 2006 season. "It's well known that I interviewed with Philadelphia last winter, and I'd like to manage again," the 60-year-old Leyland said in September 2005.
He was announced as the new Tigers manager just one day later.