And he won the Manager of the Year award three times.
Leyland’s chance came in 1982, when La Russa, then the new manager of the Chicago White Sox and a player he had played against in the minor leagues since 1979, offered Leyland the third base coaching job. Leyland spent four seasons on La Russa’s coaching staff and interviewed for several managerial positions, including with the Houston Astros, but was unsuccessful. In 1985, he got a call from Pirates general manager Sid Thrift asking permission to interview for the managerial position.
“I actually thought one of my brothers was joking,” Leyland says, “because they were always complaining that I was a bridesmaid and I didn’t get the job. So when he said, ‘This is Sid Thrift,’ I said, ‘Yes, I’m Casey Stengel.'”
Once Leyland was convinced it wasn’t a prank call and that the Pirates were serious about him taking the job, he took his first major league job and never looked back. After 11 seasons in Pittsburgh, Leyland joined the Florida Marlins and led them to a World Series victory in 1997. He moved to Colorado in 1999, but grew tired of trying to win at a mile-high altitude and abruptly left after the season.