He was the winner of the Best Manager award three times.
Leland got his chance in 1982. La Russa, the new manager of the Chicago White Sox who had been managing games against Leland since 1979 in the minor leagues, offered Leland a job as his third-base coach. Leland remained on La Russa’s coaching staff for four seasons, interviewing for several managerial jobs, including with the Houston Astros, but never got a job. He got a call from the Pirates in 1985 from general manager Sid Thrift asking permission to interview him for a managerial position.
“I actually thought one of my brothers was playing a prank on me,” Leland said, “because they always blamed me for being a bridesmaid and never getting the job. So when he said, ‘This is Mr. Thrift,’ I said, ‘Yes, and I’m Casey Stengel.’”
Once Leyland was convinced that this was no joke and that the Pirates were serious about hiring him as manager, he took his first big-league job and never looked back. After 11 seasons in Pittsburgh, Leyland joined the Florida Marlins and led them to the 1997 World Series title. He left for Colorado in 1999, but abruptly resigned after the season, frustrated with trying to win at such a high altitude.
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