The Phillies’ offseason began with a proclamation from team owner John Middleton. “We’re going into this expecting to spend money,” he told USA Today. “And maybe even be a little bit stupid about it.”
Taken at face value, the statement might feel silly. The easiest and quickest way to win is to spend money, after all. If you want to win—any team owner’s goal, ostensibly—it should be stupid not to enter free agency expecting to spend money. But “stupid” is flexible, shifting relative to baseball’s definition of “smart.” These judgments tend to rely on process rather than outcome, and a smart process is one that displays innovation and good timing.