NEW YORK, NEW YORK – OCTOBER 08: Manager Aaron Boone #17 of the New York Yankees speaks to the media before game four of the American League Division Series against the Toronto Blue Jays at Yankee Stadium on October 08, 2025 in New York City.  (Photo by Ishika Samant/Getty Images)

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Jackson Roberts

By Jackson Roberts

Contributing Sports Writer

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After yet another season of playoff disappointment, the New York Yankees are back to answering questions about what needs to change.

Sixteen straight seasons without a championship is a disaster for the Yankees franchise, as it’s now tied the second-longest drought in franchise history. (The longest was 19, from 1903 to 1922.) The Yankees just haven't built the roster to secure that first title since 2009, and this will be another offseason of trying to construct the right mix.

The outfield will be an X-factor in this Yankees offseason, as no other part of the roster stands to lose more talent in free agency. But there's also plenty more talent left behind even if both main free agents depart.

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NEW YORK, NEW YORK - OCTOBER 08: Manager Aaron Boone #17 of the New York Yankees speaks to the media before game four of the American League Division Series against the Toronto Blue Jays at Yankee Stadium on October 08, 2025 in New York City.  (Photo by Ishika Samant/Getty Images)

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The free agents in question are Cody Bellinger, who was the Yankees' second-most consistent position player behind Aaron Judge this season, and Trent Grisham, whose 34 home runs were second behind Judge for the team lead. Will either or both be back in pinstripes on opening day?

As the dust settles on the Yankees' playoff loss to the Toronto Blue Jays, it will be a while before we know those answers. But if manager Aaron Boone had his way, both outfielders would be back in New York.

"They're a big reason why I was so excited about this club down the stretch," Boone said Wednesday night, via YES Network. "Just really proud of who those guys were and are, and what they became as players, as driving forces for our team.

"What they brought to the table as teammates every single day, I appreciate that. I'm grateful to get to have managed those two guys. Hopefully in both cases I get to keep doing it."

With former top prospect Jasson Domínguez spending most of the second half of the season on the bench, it would make sense for the Yankees to let one of the two go. Grisham seems like the more likely option, as the Yankees can tender him a qualifying offer and then collect an extra draft pick if he rejects that offer and signs elsewhere in free agency.

Fittingly enough, Grisham and Bellinger made the last two outs of the season. Now, we wait to see if those were their last at-bats in pinstripes.

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