The Yankees’ failure to extend Aaron Judge is a huge mistake

I can’t quite believe I’m actually writing this article right now, but here we are. This winter, we sat by and watched as the Yankees front office passed up one of the most loaded free agent classes in recent memory despite glaring holes in the roster. The justification for this decision, we were told, was two-fold: (1) the Yankees have a crop of young talent that they didn’t want to block, and (2) the Yankees needed money to extend Aaron Judge. We can debate the tenets of the wealthiest franchise in the game banking their present success on prospects all we want—in fact, I’ve already done that in the past—but I’m far more concerned about the financials this time around, because they simply do not add up.

The logical first point of contention that has to be acknowledged from the jump is a lack of extension for Aaron Judge early on in his career. Josh already covered that a while back, and he did a much better job of explaining why it was a terrible decision than I could ever possibly do here, but it’s worth remembering before we get into the messiness of yesterday’s announcement that it did not have to be this way. Judge should have been locked up a long time ago.

In the context of the 2022 New York Yankees, I’m not entirely sure how you can look forward to the end of the season and not expect an extension to have been done. At the end of this year, Aroldis Chapman and Zack Britton are both free agents, meaning that, in all likelihood, $34 million is coming off the books. In addition to Britton and Chapman, there is also the possibility that Anthony Rizzo doesn’t pick up his player option ($16 million) and Jameson Taillon and Chad Green, who make a combined $9.8 million, will likely be hitting the free agent market as well. All told, that could add up to $59.8 million (or $43.8 million, should Rizzo pick up his option) coming off the books at the end of this season. For even the most frugal of teams, one would think that between $45 million and $60 million would be more than enough wiggle room to extend your fan-favorite superstar and still build out a roster around them.

On top of these contracts coming off the books, at the end of the season, there is also the fact that the team appears to be poised to hand over the reins to a new young core of talent—including Anthony Volpe and Oswald Peraza—as early as next year. If these prospects pan out the way we are all hoping they do, the Yankees will be getting a ton of production from at least one premium position for basically league minimum. From a financial standpoint, that is a staggering value that, theoretically, should free up even more cash to be circulated amongst other players. Like, you know, paying the current face of your franchise to stick around a little bit longer.

Speaking of value, though... Peter Brody, always extremely helpful, sent this chart to me right before I started writing this article:

This chart outlines fWAR/650 since 2017. Aside from the unexpected presence of Tyler Flowers at nine, one thing should stand out to you about this data: Aaron Judge has been the third-most productive player in baseball over the last five years. There is literally no argument that can be made against Judge being a top-tier superstar in this league, so it appears that the Yankees have undervalued his true market value. Brian Cashman went public with the fact that the Yankees offered Judge $213.5 million ($30.5 million per year, with a salary of roughly $17 million for 2021). This would pay the third-best hitter in baseball over the last five years less money per year than Max Scherzer, Gerrit Cole, Mike Trout (okay, fair), Stephen Strasburg, Anthony Rendon, Francisco Lindor, Trevor Bauer, Corey Seager, Nolan Arenado, Miguel Cabrera, and David Price.

Of course, this all comes with the very big caveat that not all hope is lost. Yes, there will be suitors for Judge’s services when free agency comes around and the Yankees will find themselves bargaining with a lot more than themselves this winter, but there is still hope that he’ll stick around to help usher in the next era of Yankees baseball. At risk of editorializing here, though, Cashman’s tone during his (incredibly poorly-timed) presser didn’t exactly instill a ton of confidence in me, and I could very easily see this being the second-coming of Robinson Canó’s free agency. The optimist in me hopes to see Aaron Judge in pinstripes for the rest of his career, but the pessimist in me, which is winning at present moment, is mentally preparing myself for someone other than Aaron Judge to be playing in right field next season.