Leyland led the Florida Marlins to the 1997 World Series championship over the Cleveland Indians, and previously won three straight division titles (1990, 1991, and 1992) with the Pittsburgh Pirates.

He spent seven seasons as a minor leaguer in the Tigers organization (1964–1970), but mainly served as a coach with the Montgomery Rebels in 1970 while playing in just two games for the team.

Leyland left the Tigers organization for the first time in 1982 when he became Tony La Russa's third base coach for four seasons (1982–85) with the Chicago White Sox, including the team's 1983 AL West division title.

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.

Pittsburgh averaged 96 regular season victories over those three years, although lost all three times in the NLCS with the latter two going the full seven games against the Atlanta Braves.

[3][4][5] In 1997, Leyland was hired by Wayne Huizenga to manage the Florida Marlins and promptly led them to the franchise's first World Championship that year, defeating the Cleveland Indians—four games to three—in the Fall Classic.

After Game 7, when asked about rumors that he might retire if Huizenga sold the franchise, Leyland quipped, "My wife doesn't like me that much.

The Tigers entered the playoffs as a wild card, and went on to defeat the New York Yankees and sweep the Oakland Athletics to win the American League pennant before falling to the St. Louis Cardinals in the 2006 World Series.

On May 1, 2012, Leyland gained his 1,600th victory as a major league manager, passing Tommy Lasorda on the all-time wins list.

[15] In 2012, Leyland led the Tigers to an 88–74 regular season record, winning the American League Central Division.

[16] Leyland joined former coach Tony La Russa as the only managers who have led two different MLB franchises to three consecutive division titles.

The United States won the 2017 tournament under his leadership, making Leyland the only manager to win a World Series and a WBC title.

[23] Leyland still keeps his home in the Pittsburgh suburb of Thornburg, Pennsylvania, where he has raised two children, Patrick[25] and Kellie with his wife Katie.

His son, Pat, a catcher/first baseman, was drafted by the Tigers in 2010 and also played in the Seattle Mariners and Baltimore Orioles organizations through 2015.

[27] His brother Tom Leyland was a priest of the Roman Catholic Diocese of Toledo for 55 years until his death in 2020, and two of his aunts were Ursuline nuns.