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Yankees Mailbag: Looking for optimism, Judge’s legacy, and Josh Donaldson

The mailbag is in a reflective mood this week.

Aaron Judge after the Final Out in Game 4 of the 2022 ALCS Against the Houston Astros Photo by J. Conrad Williams Jr,/Newsday RM via Getty Images

Good morning everyone, it’s time for another edition of the mailbag. Remember to send in your questions for our weekly call by e-mail to pinstripealleyblog [at] gmail [dot] com.

Mumble1 asks: My question as a lifelong Yankees fan is why should I have any optimism for next year at all when you have a stubborn general manager who continues to try to defy Einstein‘s theory of insanity. Doing the same thing over and over and expecting different results.

I’m not going to defend Brian Cashman’s recent work, partially because I’ve personally critiqued it in the past and partially because it’s been done ad nauseum at this point. The future is the focus of this discussion, and while the restraints that the Yankees impose on themselves are frustrating, they’ve shown that they can still compete with them in place. Everything crashed and burned in the ALCS this year, but outside of a total offensive blackout this team should be in the conversation to win it all regardless of what they do in the offseason.

Could they make better moves to go all-in or at least move closer to being dominant? Sure, and I would love it if they did — but they won’t. They’ve drawn that line in the sand and made it completely clear, so if you care about this team you unfortunately have to go in accepting that. From there, MLB is certainly doing their part to make the randomness of the postseason a feature and not a bug. While I disagree with their methods and the degree to which they operate around that, I can’t fault the Yankees for recognizing this fact. Now they just need all of their luck to not abandon them in critical moments time after time.

Stephen M. asks: If Judge signs elsewhere this offseason, do you think that the Yankees retire his number? Maris wasn’t one of the all-time Yankee greats, but the record cemented his number being retired. Curious if you think Judge gets the same?

Since we’re in the offseason proper now, and it’s at least a somewhat reasonable possibility, I suppose we could entertain this world for a moment. If Judge were to have played his last inning in pinstripes, I do think that the Yankees would retire his jersey eventually. He’s made his mark on this franchise in so many ways, with last season definitely putting the bow on the entire package, and while he doesn’t have a ring like Maris does he already has altered the franchise in other ways. They were willing to carve out a section of the stadium itself purely to honor him in his first full season as an MLB player after all — I don’t see a world where they wouldn’t give him that recognition.

jmack175 asks: What are the chances The Yankees will be able to off-load Josh Donaldson prior to next season? Or will we have to listen to the Yankees PR machine continue the Josh Donaldson apology tour next year?

Our own Peter Brody took a stab at this scenario earlier in the day, but I do think the odds are quite low currently. The Yankees have well and truly stabbed themselves in the foot with the Donaldson-IKF trade, and there’s a good chance that they ride out the downside of it. Donaldson’s deal lasting for just one more year gives the slightest chance that he could be moved, either with prospects to eat the money or with a partial payment and lesser prospects, but it also enables the team to simply wait out his deal and start over fresh next year.

It would be one thing if it was just underperformance — a poor bat with noticeably-excellent fielding could still earn a starting spot on plenty of teams in the right deal. Donaldson’s past complicates the process significantly, however, as most teams were only willing to put up with him when he was an All-Star level talent with MVP upside. He’s burned plenty of bridges in the time since he was at that peak, and had his fair share of controversies with his current employers to warrant a do-not-approach level of caution from rival GMs. It’s not totally out of the picture, but I wouldn’t bet on Donaldson leaving anytime soon.