The future of secretive Aaron Judge will be the focus as winter meetings begin

Aaron Judge commanded much of the attention paid to Major League Baseball during the 2022 regular season, hitting an American League-record 62 homers and breaking a record that had been set by Roger Maris 61 years earlier.

Judge’s free agency is likely to do the same at baseball’s annual winter meetings this week in San Diego.

As Astros third baseman Alex Bregman put it to Newsday during this year’s World Series: “I think the whole league will be following it. He’s the MVP of the league and he’s a free agent, and not often the MVP is a free agent.”

After hitting .311 and leading MLB in homers, RBIs (131), runs (133), on-base percentage (.425), slugging percentage (.686), OPS (1.111) and total bases (391), Judge won his first AL MVP in a landslide, capturing 28 out of a possible 30 first-place votes.

Though there has been heavy speculation that Judge will sign before the end of this year’s winter meetings (the Yankees   remain the favorite), that is far from a universal thought in the game.

“I’m not so sure about that,” one National League executive said of Judge signing during the meetings. “I could see it taking a little while.”

That, of course, isn’t a universal industry thought, either, and Judge’s handling of his free agency to this point is the primary reason for such disparate opinions.

The outfielder is fiercely private and thought contract negotiations would be conducted that way, the reason he was irritated when on Opening Day, the Yankees publicized the seven-year, $213.5 million extension offer he turned down.

What is known isn’t much, and it amounts to this: Judge has met with the Giants, the team the California native grew up rooting for and a team that has signaled its intent to spend big this offseason, and he has a significant offer from the Yankees, one “in the neighborhood of eight years and $300 million,” according to an ESPN report this past week.

Those kinds of numbers — both the years and dollar amount — are in line with what most in the sport predicted Judge would be looking at as the regular season unfolded.

As another NL executive said, however, eight years and $300 million “may well be a starting point.”

“I would think he’ll be able to do better than that; [maybe not] the years but certainly the money,” the executive said.

He added: “But no one seems to really know what [Judge] is thinking." 

That's exactly how Judge and his representation prefer it. Dating to spring training, they wanted all contract talk kept as secret as possible.

That is why the Yankees' offseason comments regarding Judge  have consisted of statements of praise and  expressions of desire to keep him.

The Giants have said — and leaked — little about their meeting with him. There are a handful of other teams — a group that includes the Dodgers, Mets, Red Sox, Cubs and Cardinals — that are considered realistic landing spots because of their potential financial muscle, but their interest, or any other team’s, in Judge is not yet known or has not yet become public.

"There's still work to be done, and we'd like to do that together with him,'' Yankees general manager Brian Cashman recently said regarding his overall roster. "He's put himself in a great position to have a lot of choices, so we've got to give him the time to play that out. He'll do what's best for him and for his family."

To a degree, the Yankees are in a holding pattern while waiting to see what Judge does — if he goes elsewhere, they will need to pivot in terms of how some of the money Judge turned down is allocated — but not completely. They’ve already re-signed first baseman Anthony Rizzo, who is close to Judge, to a two-year, $34 million deal with a $17 million club option in the third year that includes a $6 million buyout. They have needs in the outfield, bullpen and starting rotation (lefthander Carlos Rodon, whom the Yankees have long liked, is among the targets in that department).

Bringing Judge back, however, is priority No. 1 for the organization, a sentiment managing general partner Hal Steinbrenner has relayed to Judge multiple times this offseason, including during an in-person meeting. 

"I just want him to know how I felt in case there was any lack of clarity or ambiguity," Steinbrenner said at last month’s owners’ meetings in New York.  "We have plenty of ability to, and Aaron and I talked about this, to make this happen and still have money to make other things happen.”