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Inside The Pinstripes

Ranking the Yankees' Biggest Offseason Needs

The Yankees have a lot of holes to fill if they want to finally win a World Series. Which one is the biggest?
Oct 28, 2024; New York, New York, USA; New York Yankees general manager Brian Cashman walks on the field before game three of the 2024 MLB World Series between the New York Yankees and the Los Angeles Dodgers at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images
Oct 28, 2024; New York, New York, USA; New York Yankees general manager Brian Cashman walks on the field before game three of the 2024 MLB World Series between the New York Yankees and the Los Angeles Dodgers at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | USA TODAY Sports via Reuters Connect

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The New York Yankees' goal for 2027 will not change: to finally win another World Series.

Yet their embarrassing ALDS exit this year showed that the Bronx Bombers aren't as close to accomplishing that goal as they hoped. Even with a healthy Aaron Judge and that loaded rotation led by Cam Schlittler, the Yankees still need a few more pieces to push themselves over the top.

The impending MLB lockout this winter may force general manager Brian Cashman to either act quickly or find creative solutions, especially if a salary cap is implemented. But he can't afford to "run it back" like he did last winter.

Here is the Yankees' list of needs to address, ranked accordingly by urgency.

4. Bullpen

This could become a much larger need to address if the Yankees aren't able to bring back David Bednar and Paul Blackburn, both of whom will become free agents during the winter. But even if they re-sign these key arms, the team still needs to add more depth to the bullpen.

After failing to bolster the unit at the trade deadline, the Yankees had to lean even more on Bednar, Blackburn and especially Brent Headrick over the course of the stretch run. Headrick in particular led MLB with 81 pitching appearances, and fatigue gradually began to set in for him.

The good news for the Yankees is there are plenty of routes to improve the unit. Adrian Morejon of the San Diego Padres would be a fantastic addition in free agency, while arms like Raisel Iglesias, Alex Vesia and old friend Jonathan Loaisiga may also be available on the open market.

And of course, the team can look at reclamation projects (much like Headrick and Blackburn) or internal options for Matt Blake to work with (assuming he returns as pitching coach). Ben Hess could possibly be called up during the 2027 season, while Elmer Rodriguez and Carlos Lagrange could see use as relievers if they don't quite cut it as starters.

3. Second Base

It's very unlikely that the Yankees bring back Jazz Chisholm Jr. at this point. The talent is there and Chisholm expressed his desire to stay in the Bronx, but his inconsistent play in 2026 and polarizing attitude make it difficult to give him what he'd want for a long-term deal unless he accepts a qualifying offer or a short-term platform deal.

The Yankees have also plugged Anthony Volpe at second base to solid results, but the sample size is too small to immediately give him the job. Volpe is also a candidate to play another position that is an even bigger need for the Bronx Bombers.

Interestingly, the second base market in free agency is deeper compared to other positions this winter. Luis Arraez and Brandon Lowe bring in two completely different skillsets that would both be effective in New York's lineup, while both showed tremendous improvement defensively. There's also Gleyber Torres, who still has defensive concerns but maintains strong on-base skills that the Yankees desperately need.

This all depends on what the Yankees decide to do with Chisholm, as he arguably has the highest ceiling of all second basemen on the market. If New York lets him go, which seems more likely, then they could look at those free agent options or give Volpe an extended look.

2. Catcher

This is a need that changed in scope for the Yankees since the trade deadline. At first, they needed any catcher because of Austin Wells' stunning fall from grace and the ineffectiveness of J.C. Escarra/Ali Sanchez. After the second half, Wells managed to reward the Yankees' continued faith in him with substantial improvement, but he can't be expected to anchor catching duties with little depth behind him, which may have contributed to that brutal first half.

Free agency has plenty of good right-handed hitting catchers, with the most notable being Ryan Jeffers. Carson Kelly is another solid backstop who crushes southpaws, while former Yankees Kyle Higashioka and Gary Sanchez fill two different needs; Higashioka is that unspectacular but serviceable backup to Wells, while Sanchez would be the more offense-oriented catcher compared to Wells' defensive prowess.

At the very least, the Yankees need to have better backup options than Escarra and Ali Sanchez, both of whom are below replacement level. Having even a serviceable backup to Wells, let alone another catcher who can start regularly, would take both offensive and defensive pressure off of him, on top of taking less of a beating behind the dish.

1. Third Base

Since Alex Rodriguez retired, the Yankees have gotten little production from third base outside of Miguel Andjuar in 2018 and Gio Urshela in 2019. Those two eventually lost their luster, Oswald Peraza eventually fizzled into uselessness, and the Josh Donaldson trade was a notorious bust.

Yet there's an argument that Ryan McMahon has been the worst to come through the Yankees' revolving door at the hot corner. His bat remains just as bad as it was in Colorado (if not worse), while his defense, which was supposed to be Gold Glove-caliber, hasn't come anywhere close to expectations. McMahon has been so bad that the Yankees might outright eat the remaining $16 million on his contract just to get rid of him.

To make things even worse, there aren't any appealing options at third base in free agency. Arguably the best one would be Bo Bichette, and it's unlikely he opts out of the extremely high AAV deal he signed with the Mets after a down year. After that is Eugenio Suarez and Alec Bohm, with the former having regressed significantly since the first half of 2025 and the latter having shown no form of consistency in his career.

This is where Cashman needs to get creative and swing a surprise blockbuster deal for a third baseman, much like he did with Donaldson (even if that failed to work out). Right now, the Yankees' best options at third are Jose Caballero, who didn't see good results there in 2026, and Anthony Volpe, who is still learning the position and doesn't have the ideal arm strength to handle it.

The fact that McMahon has become unplayable is extremely unfortunate, because there aren't any ways for the Yankees to solve their third base problems without taking a massive risk or getting very little reward.

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Joe Najarian
JOE NAJARIAN

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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