ORLANDO – When he arrived at the Winter Meetings Sunday night, Brian Cashman insisted he did so without harsh restrictions from Hal Steinbrenner on his offseason spending.
The Yankees GM, who is pursuing a reunion with Cody Bellinger and hopes to strengthen his bullpen, talked about how he would like to add a starter and also find better lineup balance than he currently has.
It would be difficult to achieve all, or even some of it, if the Yankees were to actually stay under the $300 million payroll — which Steinbrenner recently said would be “ideal” — given that they are already projected to be around $283 million.
“The last time I talked to you guys, I told you guys that Hal didn’t give me a drop-dead number and that’s still the case,” Cashman said in a hotel room at the Signia by Hilton Orlando Bonnet Creek. “Hal’s exact words to me remain: ‘Take whatever is there, to me,’ which I will continue to do.”
Cashman claimed Steinbrenner did not order him to cut payroll from the $319 million the Yankees made last season, which ended in the ALDS against the Blue Jays.
When asked if the Yankees should realistically spend more to improve their roster from last year, Cashman replied, “There’s a lot of different ways to skin a cat.”
“I think that belongs to every owner [ideal] – you’d like to win the whole thing at a lower price, if that’s possible,” Cashman said.

Still, Cashman indicated that the tenor of his conversations with Steinbrenner have not changed this offseason, noting that the Yankees increased their payroll at the trade deadline last season despite exceeding the top luxury tax threshold.
The top tax threshold for next season is $304 million, a figure the Yankees would almost certainly blow past if they can land Bellinger.
Cashman reiterated Sunday that they “would love to have him back if it was a good fit for us,” noting that he spoke with Bellinger’s agent, Scott Boras, on Saturday.
If the Yankees miss out on Bellinger, they could fill the left field hole internally with Jasson Domínguez and/or Spencer Jones, although that would also be a position filled by a left-handed bat (Bellinger also hits left-handed, but he mashed left-handed pitching in 2025).
Perhaps that would free up money for the rotation (which is expected to bring back Carlos Rodón from the injured list in April or May, and Gerrit Cole in May or June) or the bullpen, which has already lost Devin Williams to the Mets.
Whether or not any of those holes will be filled by the time Cashman leaves the Winter Meetings remains to be seen.
“Last year we were able to get a lot of things done during the Winter Meetings and beyond,” he said. “So I don’t think there’s as much of a need for a lot of things as there was last year. But there are things that I’m obviously trying to do.”
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