He was the long-time manager of the Pittsburgh Pirates from 1986 to 1996. It was in Pittsburgh that Leyland became what many regard as one of the best modern-day managers in baseball, along with Tom Kelly and Tony LaRussa. He won two manager of the year trophies with the Pirates in 1990 and 1992 and developed such all-stars as Bobby Bonilla, Jay Bell, Tim Wakefield and Barry Bonds in Pittsburgh before a fire-sale in the mid-1990s soured him with local management. Under Leyland, the Pirates went to the National League Championship Series in three straight seasons (1990, 1991, and 1992). Unfortunately, Leyland's Pirates lost all three of those NLCS, with the latter two going to the full seven games. Although he has moved on in his career he still keeps his home in Pittsburgh.
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. The Marlins, in only their fifth year of existence, became the fastest expansion franchise to win a World Series (a feat that has since been broken by the 2001 Arizona Diamondbacks) In the offseason, Huizenga dismantled the team in what became known as "the fire sale." Leyland remained as the manager, but resigned after the disastrous 1998 season. At his press conference, Leyland remarked that he 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. When he left managing after the 1999 season, he became a Pittsburgh-based scout for the St. Louis Cardinals; he was often 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 contender 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 then-60-year-old Leyland said in September 2005. He was announced as the new Tigers manager just one day later.
As of July 4th, Leyland has guided the Tigers to a 56-28 record, currently the best in the majors and the Tigers best start since 1984.