When you consider that the Yankees' inability to translate regular-season dominance into a pennant over the past three years is largely a product of running into the Astros in October, that simple observation tells you why Brian Cashman and the Steinbrenners were willing to go all-in on Cole with a nine-year, $324 million contract that is the richest ever given to a pitcher.
Of course there is risk. Even for the Yankees, in a luxury-tax world, one that will change when the next collective bargaining agreement is eventually figured out, $324 million is a hell of a lot of money. And Cole is a pitcher, a word that by itself almost serves as a cautionary tale. But in this case, the risk was worth taking.