All of what you say

All of what you say about the Pettitte situation makes sense from a financial standpoint. Yes, if Pettitte gets hurt then the Yankees look foolish (though we know that they aren’t out the full value of the contract because of insurance) but not that foolish because then they go out and sign someone to replace the hurt AP. Sure, Cashman has freedom now, but he’d have it even if Pettitte were signed, so don’t fool yourself. But for one thing it’s unlikely that they would have actually overpaid for him – particularly if they had gotten to him before his stellar second half. If they re-upped him during the season there would be no danger of him bolting to the Astros, initiating a necessary blowout signing of Colon or Millwood (which might happen anyhow) or worse, a trade of Johnson of Soriano for Vazquez. There was really very little downside to getting him on board before he was able to file, particularly not when there are no real financial constraints (the fact that the Yankees will willingly pay the luxury tax proves that point). Your argument makes tremendous sense if taken out of Yankeeland context. Pettitte has been a vital part of the last several years, and there is now a reasonable (not high, but modest) risk that the Yankees may not have him next year, no matter what they offer. Remember, he would not have had any opportunity to be seduced by the idea of playing near home if he hadn’t been given the opportunity to file in the first place. That is tautological, perhaps, but no less important. So, summarizing: Best possible upside: Pettitte re-signs, slightly overpaid, maybe underpaid, or, potentially at fair market, who the heck knows. Worst possible downside: Pettitte bolts, Yanks have to pay 40M to (fitness-happy) Bartolo Colon for 3 or 4 years or, even worse, trade one of their best youngsters (or, put in perspective, one of the best youngsters in all of baseball) for Vazquez, all to cover the fact that they lost one of the linchpins of their team, a true gamer. So, I understand your take, but I don’t necessarily see this as anything close to good risk management. (Disclaimer: These suppositions all depend, of course, on the Yankees’ brass having as high an opinion of Pettitte as I do. Perhaps I am missing something?)

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