Brian Cashman has been general manager of the New York Yankees since 1998. That credential alone virtually ensures Cashman’s enshrinement. By the time his current contract expires in 2028, he will have served as the chief executive of one team longer than anyone in the game’s history who didn’t also own the team.
In 2021 Cashman eclipsed the record of 22 years held by the prototype of Yankee general managers, Hall of Famer Ed Barrow (1921-1943).
Under Cashman, the Yankees have a .587 winning percentage with World Series wins in 1998, 1999, 2000 and 2009, and American League pennants in 2001 and 2003.
It was noted above that Cashman will set the record for consecutive seasons running one team, but that statement comes with a two-word qualifier: Billy Beane. He was also hired in 1998 as GM of the Oakland so either Beane and Cashman will hold the record at the moment the other retires.
Beane’s contribution, of course, is not just his team’s success but his enduring role in changing the way front offices operate. He was the father of the shift from pure scouting to analytics as an evaluative tool, a change motivated by the need to overcome his franchise’s persistent small-market status. Promoted to team president in 2016, Beane’s Athletics have won 11 postseason berths, although that success has not translated to any World Series appearances.