5 Free Agents Yankees Should Pursue to Keep World Series Window Open in 2027

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After the New York Yankees were eliminated in the ALDS, Aaron Judge urged the front office to go "all-in" on assembling a World Series-caliber roster.
That may not be easy, though. Even if the Yankees get a fully healthy Judge as they did in 2024 and 2025, they aren't just one piece away from a pennant. Multiple areas of the roster need improvement, primarily to upgrade the offense.
Fortunately, the Yankees can turn to the free agent market for help. While the free-agent class seems thin on position players, it actually has several clear-cut options that address the Bronx Bombers' critical weaknesses. The possible introduction of a salary cap would make it harder to land some of these players, but that provides more reason for the Yankees to act quickly and bring in talent before the CBA expires on December 1.
Here are five free agents the Yankees should pursue to go all-in for 2027.
Ryan Jeffers, C

While Austin Wells turned things around after a miserable first half, the Yankees can't afford to rely so heavily on him with Ali Sanchez as his backup. Perhaps bringing in a proven starting catcher to share the job with Wells would help him maintain consistent production, and Ryan Jeffers is the best option available on the market.
Despite being limited to 92 games this season, Jeffers was very impressive at the plate with a .256/.353/.461 slash line and 14 home runs. The 29-year-old has also been great against left-handed pitching, logging a career .829 OPS. Given Wells' struggles against lefties in his career (.578 OPS), having someone like Jeffers platoon with him would be ideal.
Also, Jeffers worked with Yankees catching coordinator Tanner Swanson in the past, so perhaps that could help with improved defense and an easy transition to catching a new pitching staff. Nonetheless, Jeffers would significantly boost New York's lineup, especially if Wells regresses as he did in the first half of 2026.
Luis Arraez, 2B

This hinges on whether the Yankees choose to bring back Jazz Chisholm Jr., but it seems more than likely that they will let him walk. Regardless, the Bronx Bombers still need a player with good bat-to-ball skills to make the lineup less polarizing, and nobody makes contact more consistently than Luis Arraez.
Despite Arraez's production dipping after being traded at the deadline to the Philadelphia Phillies, the 29-year-old enjoyed a bounce-back year by hitting .310 with a solid .765 OPS. He did that while striking out just 28 times in 596 plate appearances. As a trade-off, Arraez also hit into 15 double plays. Arraez was labeled a poor defender in the past, but he bucked that trend with outstanding defense at second base in 2026, further bolstering his market value.
If the Yankees decide to pursue Arraez, they should look to help him improve his plate discipline. Getting Arraez to draw more walks would further complement his ability to avoid strikeouts and make him one of the toughest outs in baseball.
Teruaki Sato, 3B

Third base has been a disaster for the Bronx Bombers for a while, yet Ryan McMahon may be the worst third baseman they've had since Alex Rodriguez left the team. At the same time, making things more difficult for the Yankees is how thin third base is leading into free agency.
But that refers to MLB players on the open market. The best third base option is currently in Japan, as Teruaki Sato is expected to be posted after winning the Central League Triple Crown. Sato, 27, slashed a monstrous .306/.383/.609 with 40 doubles and 39 home runs in the NPB's pitching-friendly environment.
There are concerns about Sato's defense at third and his plate discipline, as he tends to chase a lot. However, Munetaka Murakami had similar concerns when transitioning to the majors and still enjoyed a tremendous rookie season with the Chicago White Sox. Sato will have an adjustment period, but taking a chance on him is a significantly better option for the Yankees than dealing with an aging McMahon for another year.
Seiya Suzuki, OF
Seiya Suzuki has been productive in his first five MLB seasons, but 2026 was when he put everything together. In addition to slashing .270/.368/.473 with 58 extra-base hits (including 26 homers), the 32-year-old emerged as a defensive asset with 14 Defensive Runs Saved in right field and an 8 Fielding Run Value, per Baseball Savant. Suzuki's 4.6 fWAR in 2026 was also the best in his career.
The Yankees would need to make quite a few moves to make this work, though. Because Suzuki is a full-time right fielder, Aaron Judge would become the everyday DH while Spencer Jones and Cody Bellinger play center and left field, respectively. It would also mean getting rid of both trade deadline additions (Luis Garcia Jr. and Heliot Ramos) and Giancarlo Stanton.
But after his injury-plagued season, Judge will inevitably be limited to DH duties in the future. And given how good Suzuki was in 2026, the Yankees' post-Judge outfield would be in very good shape if they sign the Japanese slugger.
Adrian Morejon, RP

One of the Yankees' priorities this winter will be to bring David Bednar back, as he looked like the team's long-term solution at closer. But even if Bednar returns, the bullpen still needs more depth, given how much the Yankees relied on Brent Headrick and Paul Blackburn.
Fortunately, electric setup man Adrian Morejon will be available in free agency. One of the most dominant setup men in baseball, the 27-year-old southpaw throws a triple-digit sinker that generates whiffs and easy ground balls.
That pitch is complemented by a devastating changeup to effortlessly put batters away. Morejon struck out 107 batters in just 86.0 innings and allowed just four home runs all season.
If the Yankees ultimately fail to re-sign Bednar, then they could take a chance on Morejon as their new closer. They could also consider this path even if Bednar returns. Regardless, Morejon would be a fantastic high-leverage addition that adds much-needed depth beyond the Bednar, Blackburn, and Headrick trio.
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Joe Najarian is a writer for Yankees On SI, having previously covered the Yankees both for SI and additional sites since 2023. He also served as Deputy Editor for the Yankees, Mets and Orioles On SI sites, and additionally contributes to Athlon Sports and Men’s Journal covering Major League Baseball and other trending sports news. Joe is a graduate of Rutgers University in 2022, earning a bachelor’s degree in Journalism and Media Studies.
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