Yankees winter to-do list: Juan Soto, Aaron Boone and where New York goes from here

The New York Yankees’ season was World Series or bust. Those are the expectations that come with acquiring a player of Juan Soto’s caliber.

So while the Yankees advanced to the World Series, they got pummeled by the Los Angeles Dodgers. The series ended in five games, with the Dodgers dominating the Yankees in every facet, and leading New York into a winter filled with extreme uncertainty. 

The most pressing question, of course, is the future of Soto. The superstar outfielder is a pending free agent and will draw interest from many teams, including the Yankees, New York Mets, Philadelphia Phillies, Los Angeles Dodgers and others. The Yankees are considered one of the favorites to sign Soto long-term – he likes New York and they have the financial wherewithal to sign him – but there are no guarantees, especially with Mets owner Steve Cohen lurking.

Here’s an offseason preview for the Yankees.

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Yankees’ free-agent targets

This list obviously starts with Soto and, really, their offseason is Soto or bust. If they lose Soto in free agency, especially to the Mets, people in New York will be calling for general manager Brian Cashman’s job – fair or not. That’s just the reality. 

With Soto, the Yankees are an entirely different team. This postseason, he has been their best player, and he has long been one of the best players in major-league baseball. Soto, 26, hit .288/.419/.569 with 41 home runs and 109 RBI this season. In seven career seasons, he’s hit .285/.421/.532 with 201 home runs and 592 RBI. 

Signing Soto will be expensive - it’ll be one of the richest deals in baseball history – and should land between $500-600 million.

Besides Soto, the Yankees’ roster will need to be significantly addressed. They have seven pending free agents and Gerrit Cole, the team’s star right-hander, has a $36 million option that he could opt out of to become a free agent. Look for the Yankees to be active in addressing almost every part of the roster: first base, outfield, infield, starting pitching and bullpen.

This will be one of the most active, and perhaps even the most important offseason, in Brian Cashman’s tenure. Getting this right is crucial.

Will the Yankees be active in the trade market?

They have to be. Really, they have to be active in exploring every avenue to upgrade this roster because of how it’s constructed in 2025 and going forward.

Cashman and Co. cannot fill this roster just through free agency. It will come internally, in the form of young players stepping into key roles. It will come through free agency. And it will come via trade conversations that will begin at next week’s General Managers meetings in San Antonio, Texas.

What free agents should the Yankees keep?

This obviously starts with Juan Soto. After all, how could it not? Besides Soto, the other Yankees’ free agents include Gleyber Torres, Alex Verdugo, Clay Holmes, Tommy Kahnle, Jonathan Loasiga and Tim Hill. Cole has a $36 million player option for next season while Luke Weaver has a $2.5 million club option and Lou Trivino has a $5 million club option.

Torres seems like the second priority for the Yankees. Torres, 27, has improved since moving to the leadoff spot, hitting .257/.330/.378 with a .709 OPS, 15 home runs and 63 RBI. In his seven-year career, he’s hitting .265/.334/.441 with 138 home runs and 441 RBI. He’s a candidate for the qualifying offer and it’s possible that he accepts it. Surely, he’s one to watch, and a player that the Yankees should seriously consider bringing back.

Cole, if he opts out, will be another huge priority. Weaver is a player that the Yankees should absolutely keep on a $2.5 million option. Kahnle, who posted a 2.11 ERA in 50 innings, should draw significant interest in free agency and is someone Cashman should attempt to bring back.