2022 Winter Meetings Primer: Where Do the Yankees Stand?

The Winter Meetings begin Sunday. Here’s a look at New York’s list of free agents, areas of need and more.

The Winter Meetings begin Sunday in San Diego, where the hot stove could ignite.

Fresh off a historic MVP season, Aaron Judge will command a good chunk of the spotlight as the Yankees try to re-sign him. But the hulking outfielder is not New York’s only free agent still on the market, and the team still has a few other areas to address after retaining first baseman Anthony Rizzo earlier this offseason.

Here's a look at where New York stands before the baseball world convenes on the California coast.

Remaining In-House Free Agents

• OF Aaron Judge
• LHP Aroldis Chapman
• LHP Zack Britton
• RHP Chad Green
• OF Andrew Benintendi
• RHP Jameson Taillon
• RHP Miguel Castro
• DH Matt Carpenter
• UT Marwin Gonzalez
• OF Tim Locastro

Top Priorities

Re-sign Aaron Judge: On Wednesday, ESPN’s Jeff Passan reported that the Yankees have made an offer to Judge in the neighborhood of eight years and $300 million. Such a deal would break the $35.5 million annual average value Mike Trout got from the Angels, a record for position players. Passan added that the Yankees could increase their offer if the Giants or Dodgers try to woo the right fielder away.

Find a left fielder: Even if the Yankees retain Judge, they still have another outfield position to fill. Benintendi was acquired over the summer to play left field, but he’s also a free agent. The Yankees could re-sign him, as Benintendi’s knack for contact still fits New York’s needs, or they could pursue an alternative on the open market or via trade. In-house left field choices include Aaron Hicks, who struggled last year, and Oswaldo Cabrera, who can play the outfield but does not have much experience there.

Add an elite starter: The Yankees don’t necessarily need another starting pitcher, but there are a few elite arms available: Justin Verlander, Jacob deGrom and Carlos Rodón. If one of those hurlers can be had, you find room. Even if they’re not attainable, re-signing Taillon or adding someone like Chris Bassitt, Taijuan Walker, José Quintana or Japanese star Kodai Senga creates more room for comfort than letting Domingo Germán or Clarke Schmidt battle for the fifth rotation spot.

Burning Questions

How far will other Judge suitors push the Yankees? The Yankees aren’t the only high rollers after Judge. The Giants, his childhood team, have already boasted about their ability to spend and met with the slugger, while it’s no secret the Dodgers can throw money around. Los Angeles loves to offer short-term deals with exorbitant yearly salaries, and the Giants have a hometown angle working in their favor. At the very least, the presence of these two N.L. West clubs gives Judge leverage, if not serious options to consider.

Just how much are the Yankees willing to spend? Let’s assume the Yankees re-sign Judge for more than $300 million. Then what? Adding a left fielder and a starter won’t cost chump change, especially if New York wants one of the aforementioned aces. There are also other holes to fill, including the bullpen. With the Yankees falling short in the postseason again, to the Astros no less, now is no time to be worrying about luxury tax thresholds.

What if Judge signs elsewhere? If the Yankees’ worst nightmare comes true, Plan B could involve an all-out pursuit of those frontline starters. It could also mean pivoting to one of the top free agent shortstops available, though that would abandon the expected youth movement at the position, which New York committed to last offseason when Isiah Kiner-Falefa was acquired to be a stopgap for prospects Oswald Peraza and Anthony Volpe.

Can the Yankees get rid of any costly underachievers? Regardless of what happens with Judge, the Yankees would love to create some financial flexibility by ridding themselves of players like Hicks and Josh Donaldson. But that will be easier said than done given their high salaries, poor 2022 seasons and recent injury histories. If the Yankees have any shot at moving those two, they may have to attach some prospects in a trade.

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• Yankees Great Don Mattingly Joins Blue Jays Coaching Staff

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