Baseball is a game of failure. Both on the field and in the front office. It's unavoidable. For as incredible a franchise as the New York Yankees are, fans in the modern era are all too familiar with the shortcomings as a result of parity, stale processes, and the overall changing landscape.
Look no further than the Los Angeles Dodgers, even. They just won back-to-back World Series, but they paid guys like Michael Conforto ($17 million), Tanner Scott ($16 million), Kirby Yates ($13 million), Blake Treinen ($13 million) and Tommy Edman ($12 million), all of whom contributed next to nothing.