3 free agents Yankees must sign before 2026 season to boost playoff chances, ft. Kyle Tucker

MLB: Playoffs-Milwaukee Brewers at Chicago Cubs - Source: Imagn
Kyle Tucker is expected to receive the biggest contract from the free agent pool (Source: Imagn)

The New York Yankees are swiftly approaching the mark for their longest World Series drought in franchise history. They haven't won a ring since 2009, when the team boasted of veterans like Derek Jeter and Alex Rodriguez.

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Currently, the team has little promise behind Aaron Judge and an above-average starting rotation, which will only be boosted with Gerrit Cole returning from injury. The team needs to get more new faces, and this offseason could be a perfect time for some handy additions.

Here's taking a look at three free agents who are a must-sign for the team to improve.

#3, Edwin Diaz

The Yankees are in need of relievers, and Edwin Diaz seems to be a perfect match for them. Their bullpen depth came under fire in 2025, as it pitched to a 4.37 collective ERA in 566.2 innings pitched. It was ranked 23rd among all MLB teams. Their closers had a 1.35 WHIP and a .242 opponents' batting average.

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Diaz opted out of his five-year $102 million contract with crosstown rivals, the New York Mets. He recorded a 3.0 bWAR in 2025, in 66.1 innings pitched in the regular season and is one of the biggest reliever names in the market.

#2, Kyle Tucker

The Yankees are in need of an offensive core that can give stability to the team as the season wears on. Aside from Aaron Judge, Giancarlo Stanton, Trent Grisham and Jazz Chisholm Jr. there are question marks over others' place in the side.

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Kyle Tucker will be the perfect addition to the Yankees to become Judge's deputy in the outfield and provide that power at-bat punch behind him in the lineup. The former Astros and Cubs slugger has recorded a 4.6 bWAR in each of his last five seasons, with four All-Star caps during that time.

#1, Cody Bellinger

The Yankees will look to re-sign Cody Bellinger to the team, not just for his offensive prowess at home, recording a .909 OPS at Yankee Stadium this past season, but also because of his versatility in the outfield. Bellinger's range and arm, coupled with his brisk at-bats, were crucial for New York.

While chances are the team will only be able to sign either Tucker or Bellinger, looking to make a splash for both free agents could fill the two vacant outfield spots that Cashman mentioned.

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Edited by R. Nikhil Parshy
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