The New York Yankees general manager Brian Cashman is the longest-tenured general manager in all of baseball. He has made some amazing acquisitions and trades over his time with the Yankees, but he has also had some terrible misses. To refresh your memory before the 2019 season, he acquired DJ LeMahieu from the Colorado Rockies for one of his best successes ever.
Cashman started with the Yankees as a humble intern in 1986, he impressed George M Steinbrenner, and six years later, he was promoted to the Assistant General Manager. From that time, he worked hand and hand with then-manager Buck Showalter and “Stick Michael,” building the Yankee dynasty of the late ’90s.