When Brian Cashman began his internship with the Yankees in 1987, he saw then GM Woody Woodward buckle under The Boss. Nicknamed The Pharmacist because of his trove of stress-relieving medication, Woodward resigned after one year. Being the General Manager for the Yankees under George Steinbrenner was just as good as an internship it seemed like.
Cashman was almost 20 then, and was just hoping the Yankees would win while he was passing through so he’d have some stories to take with him. He worked in the minor league scouting department by day, and the security office by night, trying to earn a few extra bucks. Little did he know the journey he was about to go on.
Cashman landed the summer intern job through a friend who worked at a Florida racetrack which was affiliated with the standardbred farm Cashman’s father, John, had in Kentucky. This friend happened to know a guy by the name of George M. Steinbrenner III.
Cashman attended the Catholic University of America, and was a four-y...