The Yankees’ winter checklist starts with the bullpen, and it might not stop there.
If New York wants to get back to its 2027 goal of finally winning another World Series, the relief corps needs more help - even if the club brings back David Bednar and Paul Blackburn, both of whom are set to hit free agency this winter. After the Yankees missed on bullpen upgrades at the trade deadline, they had to lean heavily on Bednar, Blackburn and especially Brent Headrick down the stretch. Headrick led MLB with 81 pitching appearances, and the wear started to show.
That leaves Brian Cashman with a wide range of options, but not much room for another winter of standing pat. The impending MLB lockout could force him to move fast or get creative, especially if a salary cap comes into play.
On the free-agent market, Adrian Morejon stands out as a strong fit, while Raisel Iglesias, Alex Vesia and Jonathan Loaisiga could also be in play. The Yankees can also look to reclamation arms or internal solutions for Matt Blake to mold, assuming Blake returns as pitching coach.
Ben Hess could surface during the 2027 season, and Elmer Rodriguez and Carlos Lagrange could be used out of the bullpen if they don’t stick as starters.
Third base looks like a much tougher puzzle.
Ryan McMahon has been a major disappointment, with a bat that has stayed as poor as it was in Colorado and defense that has not lived up to the Gold Glove-level billing. It has gotten so bad that the Yankees might even consider eating the remaining $16 million on his contract just to move on.
And the problem is made worse by a weak market. Bo Bichette would be the prize, but it’s unlikely he opts out of the extremely high AAV deal he signed with the Mets after a down year.
After that, the options thin out quickly with Eugenio Suarez and Alec Bohm, neither of whom offers much certainty.
That means Cashman may have to swing big in a trade, the way he did with Donaldson, even if that move didn’t work out. For now, Jose Caballero and Anthony Volpe are the names at the position, and neither is a clean solution. Caballero didn’t produce there in 2026, while Volpe is still learning the spot and doesn’t have the ideal arm strength to handle it.
Second base is tied to the Yankees’ decision on Jazz Chisholm Jr.
A reunion looks unlikely at this point. Chisholm wanted to stay in the Bronx, but his uneven 2026 and polarizing attitude make a long-term deal hard to justify unless he settles for a qualifying offer or a short-term platform contract.
If he’s gone, the Yankees can turn to a second-base market that is deeper than most this winter. Luis Arraez and Brandon Lowe bring very different skill sets, but both could fit New York’s lineup, and both improved defensively.
Gleyber Torres is also out there, though his defense still comes with questions even as his on-base ability remains a major draw for a Yankees club that needs it.
Catching is another area that changed shape as the season went on.
At the trade deadline, the Yankees looked like a team that needed almost any catcher after Austin Wells’ rough first half and the struggles of J.C. Escarra and Ali Sanchez.
Wells turned things around in the second half and earned the organization’s continued trust, but he still can’t be asked to carry the entire catching load without help. Right-handed hitting options are available in free agency, with Ryan Jeffers leading the list.
Carson Kelly is another solid choice because he punishes lefties, while former Yankees Kyle Higashioka and Gary Sanchez each fill different roles - Higashioka as the steady backup type and Sanchez as the more offense-minded option.
At minimum, the Yankees need better support than Escarra and Ali Sanchez. A competent backup for Wells, or even another catcher who can handle regular starts, would ease the load on him on both sides of the ball and take some of the punishment off his body.
For all the attention on the lineup, the Yankees’ offseason is really about fixing the weak spots that showed up when the pressure was highest. The bullpen needs depth.
Third base needs an answer. Catcher needs a real backup plan.
And second base could swing based on what happens with Chisholm.
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