The Yankees and Brian Cashman have a long offseason ahead of them.
After several key agents left in free agency, Cashman will look to retool his outfield and bullpen — and perhaps add another starter — before the start of the 2026 season. One chip that has fallen the Yankees’ way is the return of Trent Grisham.
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The veteran outfielder accepted his qualifying offer and gives Cashman another outfielder alongside Aaron Judge. However, Cashman isn’t necessarily content with just bringing in Grisham. He’s been in contact with agents for the top two outfielders in the free agent market: Cody Bellinger and Kyle Tucker.
“We’d love to have Bellinger come back,” Cashman told the media Thursday night at his annual Covenant House Sleep Out in NYC. “Talked to [agent Scott] Boras yesterday about Belli and other free agents of his. Talked to Casey Close about his free agents; he’s got Kyle Tucker, amongst others. That’s the nature of the beast in the winter. Had several conversations with teams today, try to find a way to make a trade or add a free agent and keep going and going and going.”
Close also represents Paul Goldschmidt, Michael King and Kyle Schwarber.
Bellinger was the team’s second-best hitter behind Judge this past season. The versatile outfielder hit 29 home runs to go along with .272 batting average and 98 RBI, all while playing a Gold Glove-level left field.
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The 30-year-old opted out of his contract this offseason and will likely look to get a big payday after doing so well in the Bronx. The Yankees aren’t the only team vying for Bellinger’s services, as the Blue Jays, Mets and even Bellinger’s old team, the Dodgers, have shown interest.
And then there’s Tucker. Arguably the best free agent hitter on the market, regardless of position, Tucker will enter free agency for the first time after being traded from the Astros to the Cubs last offseason.
The 28-year-old had a solid year, blasting 22 home runs and driving in 73 runs while hitting .266 on the North Side. He made his fourth All-Star team in 2025 and won his second Silver Slugger this offseason.
Whether Cashman can pull off that signing is yet to be known, but the veteran GM is doing his due diligence to try and get the Yankees their first World Series win since 2009. And Cashman knows he needs to make his team better, and he hopes to do that this winter.
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“The team that we had last year, which was really good on paper, but fell short of our ultimate goal, is now depleted because of free agency,” Cashman said. “We have to at least get back to where we were, but the ultimate goal is to make it better. Got a lot more work to do and the whole winter to do it.”
