In a season four episode of “Mad Men,” the principal characters’ firm is about to go under thanks to the exit of a big account. When confronted with this, they have to put up a personal stake as collateral for the bank. Upon telling this to his wife, Pete (played by Vincent Kartheiser) gets the following response from his wife, Trudy (played by Alison Brie), “You bet big and lose, you don’t double down.” It’s likely sound advice, but, just for today, I’m proposing the Yankees go against it and making a case for keeping Sonny Gray around.
The Yankees bet (fairly) big to bring Gray to the Bronx at the trade deadline in 2017, trading away prospects Dustin Fowler, Jorge Mateo, and James Kaprielian to the A’s.