Inside The Pinstripes

Yankees Might Have Hugely Disappointing Offseason

New York Yankees fans are not going to like what this insider had to say about the team's offseason plans.
Aug 28, 2025; Chicago, Illinois, USA;  New York Yankees outfielder Cody Bellinger (35) celebrates with  designated hitter Aaron Judge (99) after they score on Bellinger’s two run home run against the  Chicago White Sox during the first inning at Rate Field. Mandatory Credit: Matt Marton-Imagn Images
Aug 28, 2025; Chicago, Illinois, USA; New York Yankees outfielder Cody Bellinger (35) celebrates with designated hitter Aaron Judge (99) after they score on Bellinger’s two run home run against the Chicago White Sox during the first inning at Rate Field. Mandatory Credit: Matt Marton-Imagn Images | Matt Marton-Imagn Images

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The New York Yankees have some big needs this offseason that they're looking to address with trades or on the free agency market: or so we would hope. YES insider Jack Curry just threw a wet blanket onto fans' offseason fire by predicting the Bronx Bombers won't have the kind of major moves fans are expecting.

According to Curry, Trent Grisham accepting a qualifying offer is all but killing their chances of resigning Cody Bellinger or pursuing Chicago Cubs slugger Kyle Tucker. Bellinger's agent, Scott Boras, is a notorious tough negotiator who will likely try to get Bellinger on a huge contract that might be disastrous if he can't play well into his thirties. Plus, Curry goes on to say, prospect Spencer Jones and Jasson Dominguez should round out the outfield with Grisham.

“What is the Yankees appetite to pursue Bellinger knowing [Scott] Boras is his agent and they have [Jasson] Dominguez and [Spencer] Jones?” he said according to Everything Yankees on X.

New York Yankees center fielder Trent Grisham
Oct 1, 2025; Bronx, New York, USA; New York Yankees center fielder Trent Grisham (12) celebrates his double against the Boston Red Sox during the seventh inning of game two of the Wildcard round of the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

Curry also predicts that the Pinstripes won't make a huge deal for a new starting pitcher and will instead begin the season with a shakier rotation as they wait for Gerrit Cole and Carlos Rodón to get healthy again. Even when they are healthy, there's no clear option for a fifth starter and the role will probably bounce between Luis Gil and Will Warren.

Should Yankees Fans Worry About Quiet Offseason?

While previous Yankees offseasons have been quiet — last year, for example, they entered the season without a solid third baseman and added Ryan McMahon despite his poor offensive numbers — its not guarantee this year will be the same.

Jones is untested in the majors and Dominguez struggled defensively no matter what outfield position he played in 2025. It seems like the Yankees, who have a reputation for sending away top prospects, are more likely to deal Jones for a veteran player with skills the team needs now. Despite Curry's predictions, other insiders reported that the Yankees have been aggressively pursuing Bellinger, with Tucker as a backup option.

New York Yankees outfielder Spencer Jones
Mar 4, 2025; Clearwater, Florida, USA; New York Yankees outfielder Spencer Jones (78) celebrates after hitting a three-run home run against the Philadelphia Phillies in the third inning during spring training at BayCare Ballpark. Mandatory Credit: Nathan Ray Seebeck-Imagn Images | Nathan Ray Seebeck-Imagn Images

It's entirely possible the Pinstripes stay quiet this offseason, with no outfielder, starter or even a relief pitcher to speak of. However, Yankees fans shouldn't just panic yet. There's several months left before the beginning of spring training, and some signs are pointing towards a Bellinger reunion, though only team leadership can know how close they are to a deal.

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Delilah Bourque
DELILAH BOURQUE

Delilah Bourque is a writer and copyeditor based out of Pittsburgh, PA. She received her Bachelor's degree from the University of Pittsburgh in 2021. After a few years in corporate marketing, she joined On SI as a full-time copyeditor and contributor to the New York Yankees On SI, as well as occasional contributions across the Pittsburgh Pirates and Pittsburgh Steelers on SI.