Aaron Judge looms over everything as Yankees enter MLB Winter Meetings

At this year’s Winter Meetings, the New York Yankees will be open for business on several fronts – examining pitching upgrades, entertaining trade ideas, and looking for additional left-handed hitting.

Of course, Aaron Judge’s free agency dominates everything in San Diego, where the meetings are being held beginning Monday.

If the reigning American League MVP locks in his 2023 address sooner than later, that provides a lot more clarity towards Yankees GM Brian Cashman’s winter plan – although losing Judge would plunge the Yanks into less desirable Plan B scenarios.

Earlier this week, ESPN’s Jeff Passan reported that the Yankees’ latest offer to Judge is in the $300 million range over eight years.

Here’s what we know, and what to watch for as the meetings progress:

Yankees’ key free agents

OF Aaron Judge, OF Andrew Benintendi, OF-IF-DH Matt Carpenter, LHP Zack Britton, RHP Chad Green, LHP Aroldis Chapman.

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Anthony Rizzo already on board

1B Anthony Rizzo agreed to a two-year, $40 million guaranteed contract with a club option for 2025.

Don Mattingly Hall of Fame watch

Don Mattingly has a chance to get to Cooperstown. On Sunday at 8 pm, the Hall of Fame’s Contemporary Baseball Era Committee will announce its results from a ballot that includes Mattingly, Fred McGriff, Dale Murphy, Albert Belle, Curt Schilling, Barry Bonds, Roger Clemens and Rafael Palmeiro.

Yankees’ Winter Meetings goals

Outfield improvements

Clearly, this begins with Judge, 30, who indicated he’d rather sign somewhere earlier to allow his club a better chance to improve around him.

And right now, it looks like a match race between the Yanks and San Francisco Giants, who hosted Judge for a visit right before Thanksgiving.

Aside from putting Judge back in right field, the Yankees are motivated to pursue a reunion with lefty-hitting Andrew Benintendi, 28, in left field.