Brian Cashman is the longest-tenured GM in baseball. He started as an intern in 1986 and was promoted to assistant GM in 1992 before being named the General Manager prior to the 1998 season. However, Cashman was reluctant to take the job. He knew that George Steinbrenner had a history of firing people in power positions any given moment. Luckily for Cashman, the Yankees went on to win the World Series in his first three seasons at the helm.
In the twenty seasons since the Yankees’ 2000 World Series victory, Cashman’s teams have experienced multiple phases with varying levels of success.