Free agent outfielder Aaron Judge Robert Deutsch-USA TODAY Sports

The Yankees wasted little time in making a new offer to Aaron Judge following the commencement of the offseason, with general manager Brian Cashman revealing two weeks ago that the team had made an updated offer to the reigning American League MVP. Judge has since met with the Giants, who were also reported to be preparing an offer. The Dodgers are also a reported suitor. Details surrounding Judge’s free agency have been sparse thus far, but ESPN’s Jeff Passan reports that the Yankees’ most recent offer was “in the neighborhood of eight years and $300 million.” That’s not a final offer, and the Yankees could increase their numbers if the market necessitates, per the report.

It’s still a ballpark figure, but that general range could potentially give Judge the largest annual value ever secured by a position player. Mike Trout, who inked a 10-year, $360M extension on top of a standing two-year, $66.5M commitment with the Angels — currently holds that distinction at $36M. (Max Scherzer’s $43.3M AAV is the top mark overall.) Establishing a new AAV record among position players would surely be of interest to Judge, and if the Yankees are truly already in the $300M ballpark, he’d at least be within striking distance of Bryce Harper’s record for the largest free-agent contract in history ($330M).

As far as the timing of a potential deal for Judge, it seems as though one could come together in relatively quick fashion. Passan indicates that there’s an expectation a deal could be completed by the end of next week’s Winter Meetings, which take place in San Diego from Dec. 4-7. That meshes with previous reporting from MLB.com’s Jon Morosi, who made similar suggestions on MLB Network when discussing Judge’s meeting with the Giants. SNY’s Andy Martino, meanwhile, writes that it would “be a mild surprise” if Judge doesn’t come away from next week’s meetings with an agreement in hand.

Wherever the present numbers stand, it’s long been clear that Judge’s bold bet on himself this past spring has paid off. Judge declined the Yankees’ best extension offer prior to the season, after which Cashman took the virtually unprecedented step of announcing the terms of the offer: seven years and $213.5M. That contract would’ve begun with the 2023 season, so Judge appears to have already secured an extra year and upwards of $80-90M in additional guarantees.

Roster Resource currently projects the Yankees at a bit more than $222M in luxury obligations. An AAV in the $36-37M range would bump that number to $258-259M, setting the stage for a second consecutive season of paying CBT penalties.

As a second-time offender, the Yankees would owe a 30% tax on the first $20M by which they exceed the first threshold of $233M, a 42% tax on the next $20M spent, a 75% tax on the next $20M and a 90% tax on any dollars spent thereafter. Judge alone would put them into the second tier and come with a penalty of around $8-9M, and any subsequent moves would be taxed heavily. The Yankees could change that calculus by finding a taker for Josh Donaldson, Aaron Hicks or a member (or members) of their arbitration class, but the team knows full well that the cost of an improved offer to Judge stretches well beyond the bottom-line numbers on the contract itself.

That improved offer, of course, comes on the heels of a historic season that saw Judge seamlessly deal with not only the pressure of the expectations set by rejecting more than $200M but also the pressure of chasing down Roger Maris’ longstanding mark of 61 home runs. Judge indeed set a new American League and Yankee standard when he belted his 62nd round-tripper of the season on Oct. 4. He finished off his MVP-winning campaign with a stunning .311/.425/.686 batting line — good for a 207 wRC+ that stands as the best offensive season in recent history. Barry Bonds was the last player to match or exceed that level, and prior to him, no qualified hitter had done so since Ted Williams in 1957. MLBTR predicted an eight-year, $332M contract for Judge when ranking him atop our annual Top 50 free agent list.

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