This Should Be the Yankees' Biggest Priority After Signing Aaron Judge at Winter Meetings

New York should transition their focus to left field after re-signing Aaron Judge and wrapping up the Winter Meetings.

SAN DIEGO — Brian Cashman leaned back in his chair with his hands resting on his head on Wednesday at the Winter Meetings, apologizing for acting a little bit off.

The Yankees general manager hadn't slept, working through the night at the Manchester Grand Hyatt in San Diego as New York took care of some pressing business, finalizing a record-setting contract to keep Aaron Judge in pinstripes.

Retaining Judge was always the top item on New York's to-do list. Judge departing in free agency would've been a franchise-altering blow for New York, a subtraction that would've either sparked a spending spree of desperation or some sort of soft rebuild in the Bronx. 

In that sense, New York's trip to the Winter Meetings was a success. The reigning MVP and face of New York's franchise isn't going anywhere. That doesn't mean Cashman has time to catch up on sleep, though. The GM recognized that this organization is "on the clock," needing to address other parts of their roster if they want to contend for a championship in 2023.

"We have some [options] lined up to be brought down, but there's a lot more planes out there circling," Cashman said.

So, who else could be headed to the Bronx this winter? 

New York has shown significant interest in starting pitcher Carlos Rodón, a player they tried to acquire at the trade deadline and the best starter remaining on the open market. 

Adding another ace to New York's rotation—a staff that already includes Gerrit Cole, Nestor Cortes, Luis Severino and Frankie Montas—would set the Yankees up for success against any opponent, even those with high-octane lineups, next season. 

The same can be said about adding another arm in the bullpen. New York reportedly signed right-hander Tommy Kahnle to a two-year deal, bringing the reliever back to a unit that was one of the best in baseball in 2022. 

Teams can never have too much pitching, that adage is the truth. But those moves would be bolstering a part of New York's roster that was reliable and effective last season. It's the offense that failed to perform down the stretch, putting up pedestrian numbers as New York hung on to their division lead before vanishing completely in the postseason.

That in mind, the Yankees must prioritize their search for a left fielder now that they re-signed Judge. There aren't a surplus of options at the position either, so time is of the essence. 

Who do you think will be the #Yankees starting left fielder in 2023?

— Max Goodman (@MaxTGoodman) December 8, 2022

Cashman has made it clear this winter that he is interested in re-signing Andrew Benintendi. Why wouldn't he be. Benintendi was a strong fit after he was acquired by New York at the trade deadline last summer. He has plenty of postseason experience and brought balance to a righty-heavy lineup. New York missed him quite a bit when he suffered a season-ending injury and couldn't return for the playoffs. 

It'll be a challenge to get Benintendi back if he doesn't want to be a Yankee. Brendan Kuty of NJ.com reported that some within the organization believe Benintendi "didn't enjoy living in New York City and might prefer a smaller market nearer his St. Louis home." It would be an even more unfortunate if Benintendi signed with the Astros in free agency, a club that has been linked to the outfielder already this winter. 

Other available assets in free agency include Brandon Nimmo and Michael Conforto. Japanese star Masataka Yoshida could've been a fit for New York as well, but he came off the board on Wednesday, signing with the Boston Red Sox. 

A trade would be another way to make sure left field is taken care of this offseason. Bryan Reynolds has asked Pirates to trade him and the Yankees are still "very much" in on the switch-hitting outfielder, but Pittsburgh is under no pressure to agree to any deal before next season. 

Unless the Yankees are comfortable making Oswaldo Cabrera their full-time left fielder—the prospect showed he can perform at the position last summer, but he's better served in a utility role—this gaping hole will need to be addressed externally. The only other internal option at the moment is Aaron Hicks, who has been a disappointment since agreeing to a lucrative extension before the 2019 season. 

Signing another ace-caliber starting pitcher would be tremendous for the Yankees. More talented arms in the bullpen is never a bad thing. But figuring things out in left field should be this team's No. 1 priority going forward.

MORE:

• Rule 5 Draft Results: Yankees Lose Another Pitcher to Mets
• Yankees Tease More Moves After Re-Signing Aaron Judge: 'We're on the Clock'
• Will Aaron Judge Be Named Captain of Yankees? It's Up to Hal Steinbrenner

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