The Yankees do not have the luxury of a leisurely offseason this time around. With a possible Dec. 1 labor shutdown hanging over the market, New York is staring at a compressed window to sort out four clear areas of need: the bullpen, third base, second base and center field.
That pressure has already shaped the club’s first major decision. The Yankees extended closer David Bednar a one-year, $23.15 million qualifying offer on Nov. 2, but did not make the same move for second baseman Jazz Chisholm Jr. Bednar now has until Nov. 17 to accept or reject the offer, and if he turns it down, the Yankees can still try to keep him on a multiyear deal while other teams join the chase.
The labor timeline is what makes all of this feel urgent. The collective bargaining agreement expires at 11:59 p.m.
ET on Dec. 1, and if owners lock out the players after that, major league transactions could stop on Dec. 2.
That leaves the Yankees less than a month to work under the current rules.
YES Network analyst Jack Curry expects New York to move before the market freezes. On The Michael Kay Show, he pointed directly to the areas the Yankees may attack first.
“When I look at the Yankees, I look at that bullpen as an area of need,” Curry said.
He also identified third base, second base and center field as spots the Yankees could address. Those are very different jobs, and that’s part of the challenge for Brian Cashman’s front office. A late-inning reliever would help stabilize the pitching staff, while changes in the infield or center field would alter the everyday lineup around Aaron Judge.
Bednar’s situation sits at the center of the bullpen conversation. He converted 35 saves in 2026 and finished with a 2.47 ERA over 64 appearances. The Yankees’ relievers as a group posted a 3.13 ERA, second best in the majors, but several bullpen pieces have already reached free agency.
That means New York’s relief work is about more than just one decision. Keeping Bednar would still leave the Yankees with innings to cover before the ninth, and losing him would create an even bigger hole at the back end.
The infield picture is less settled. The Yankees were willing to make Bednar the qualifying-offer bet, but not Chisholm, even though second base remains one of the positions they need to address.
Third base is also in play, with the Yankees linked in outside projections to Japanese slugger Teruaki Sato. That is only a projection, not a completed deal or formal offer.
There are other names in the mix as well. Tarik Skubal has come up in discussions of possible Yankees free-agent targets, though landing a top-tier starter would take resources that might otherwise be spread across several needs. New York’s rotation depth gives Cashman room to weigh that kind of move against the bullpen and lineup issues Curry highlighted.
Other offseason projections have included Luis Arraez for second base, Ryan Jeffers behind the plate and former Yankee Jake Bauers. Jeffers also received a $23.15 million qualifying offer from Minnesota, which could add draft-pick cost if he rejects it and signs elsewhere.
Center field is another open question after Trent Grisham reached free agency. If the Yankees fill second base and the bullpen while leaving center field for later, they will still be juggling multiple roster problems at once.
The calendar is what turns all of this into a sprint. Free agents became eligible to sign with new clubs on Nov.
2, Bednar’s deadline arrives Nov. 17, and teams face a Nov. 20 non-tender deadline before the CBA expires on Dec. 1.
The Yankees handled the 2021-22 lockout by waiting to make their biggest moves until business resumed, but this winter offers a different choice: get deals done now or risk a stalled market once the shutdown hits.
As of Nov. 5, Cashman and Boone are still in place, and the Yankees have not announced a major signing to address the four spots Curry flagged. The next few weeks will tell the story, with Bednar’s decision and the Dec. 1 expiration setting the pace for everything that comes next.
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