The Yankees are still winning games, but the road ahead is getting rocky. More than six everyday players can hit the open market after the season, and that can leave a team in a dangerous spot.

Names like Jazz Chisholm Jr., Trent Grisham, and David Bednar are part of that group, and that is where the fear starts, especially given MLB’s recent growing extension trend.

What's the trend? Young ballplayer looking for long-term financial security. On April 15, 2026, Kevin McGonigle of the Tigers inked an eight-year, $150 million contract extension, which will keep him in Detroit until 2034.

Just a few days prior, Pirates Konnor Griffin signed a nine-year, $140 million contract. The list only goes on with others like Samuel Basallo, Roman Anthony, Bobby Witt Jr., Julio Rodriguez, and Fernando Tatis Jr.

Reportedly, out of the 141 players projected to reach at least 7.0 WAR by the end of 2028, only 10 can become free agents after this season.

The trend leaves the free-agent market in limbo.

And as Kento Mizuno put it, "Where does all this leave the Yankees? In pretty dangerous territory, if you ask me…. Two up-the-middle positions, center field and second base, will be vacated at year’s end, when Grisham and Jazz Chisholm, Jr. are set to become free agents."

Fresh off a 30/30 season in 2025, Chisholm is reportedly seeking a historic payday.

CBS Sports’ Mike Axisa said Chisholm’s camp could be looking at Willy Adames’ seven-year, $182 million deal as a rough guide, but MLB reported that there have been no extension talks yet. Chisholm, however, said that he would love to remain in pinstripes.

The Yankees have already spent big to keep Cody Bellinger and Grisham last season. And given the record that they do not hand out major extensions frequently, a potential breakup feels very much possible.

So who can replace the production? Here again, Mizuno noted, "We’re looking at names like Brandon Marsh, Cedric Mullins, or Mickey Moniak at center field, or Gleyber Torres, Mauricio Dubón, and Brandon Lowe for second base. They might be fine stopgaps, but they’re not much more."

And the uncertainty does not stop there; the rotation is carrying its own set of questions.

The Gerrit Cole problem is part of the same story

Gerrit Cole is another big piece of this puzzle. He is still under contract through 2028 on the original nine-year, $324 million deal.

Cole missed the entire 2025 season after TJ surgery. During the 2024-25 offseason, Cole's agent, Scott Boras, attempted to leverage an opt-out clause to force an extension.

Boras asked the Yankees to add a $36 million option for the 2029 season to void the opt-out. But owner Hal Steinbrenner and GM Brian Cashman firmly declined, refusing to bet more money on an uncertain elbow.

That left the deal in place as it was, with $144 million still owed at the time.

Cole last pitched for the team in 2024. He posted 8-5 with a 3.41 ERA in the regular season and 1-0 with a 2.17 ERA in the postseason.

He is currently in the midst of a rehab assignment in the minor league and looking to return to the big leagues in mid-2026.

The future of Cole's tenure in New York likely hinges on how his elbow responds during the 2026 season.

And Cole is not the only clock ticking in the Bronx. Stanton’s deal runs through 2027, Ryan McMahon’s through 2027, Cole and Carlos Rodón through 2028, and Bellinger has opt-out chances after 2027 and 2028.

Do you think the Yankees can hold this roster together or is a rebuild quietly on the horizon? Drop your thoughts in the comments down below.

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Written by

Md Saife Fida

Edited by

Utsav Gupta