Crawford is a data point in their favor, absolutely. He was a similar player to Ellsbury, and he got a similar contract to Ellsbury, and it didn’t turn out to be a very good idea. Crawford is absolutely evidence that this contract could be a big mistake. Crawford is a reminder that big free agent deals often turn out badly. But if you’re going to use Carl Crawford as the sole data point in your belief that players like Ellsbury are bad investments, you’re simply ignoring the fact that history doesn’t actually agree with you. . . .
Carl Crawford’s production is not Jacoby Ellsbury’s fait accompli; it’s one possible path of many. Every player’s future is a probability distribution, bottoming out at completely and utterly useless. Every single player could turn into a total dud tomorrow. And every single player could actually play better in the future than they have in the past. There is no single example that represents the expected outcome for any other player, no matter how similar they might appear to be. . . .
The Yankees paid a lot of money for a very good player. That very good player is probably going to remain a very good player for the next few years, and then, like nearly every free agent, he’ll be an overpaid albatross in the last few years of the deal. For the price, the Yankees probably overpaid relative to the going market rate of wins. But because they’re the Yankees, the fact that they overpaid by $20 or $30 million doesn’t matter all that much.