There are a bunch of ways to analyze this. One is to compare the most similar players to Sabathia at the same age. The most similar is Dave McNally, who at the same point in his career had 70 wins left in his arm. So that would be about $2.4 million per win. But that’s actually one of the most optimistic comparisons for Sabathia’s hypothetical future. The most similar pitcher to Sabathia overall, without regard to age, is Freddy Garcia. The first eight years of Garcia’s career look uncannily like the first eight years of Sabathia’s. Garcia has won two games in the last two years and it’s unclear whether his career will continue. So that would be $85 million per win.
Another very similar pitcher is John Tudor: he had 22 wins left when he had thrown a similar number of innings. So that’s $8 million per win. Then there’s Alex Fernandez: he had 11 wins left in his arm. The list goes on: Denny McClain, Teddy Higuera, Jack McDowell . . . it’s a pretty grim set of stat lines for sinking $170 million into one player (the one really similar pitcher who would have been “worth” this kind of contract in current dollars is/was Greg Maddux).
Sabathia’s future is also clouded by the closely related “pitching 1000 MLB innings before you’re 25 rule” (the rule is that this is generally a very negative indicator for what a pitcher will end up doing once he starts approaching 30).
But hey it’s only money . . .