Yankees principal owner Hal Steinbrenner speaks during a news conference...

Yankees principal owner Hal Steinbrenner speaks during a news conference to name Aaron Judge captain at Yankee Stadium on Dec. 21, 2022. Credit: Getty Images/Dustin Satloff

Among the most common questions bandied about at the just-concluded winter meetings in Orlando were some form of the following:

“Are these the most boring meetings in years or is it just me?”

“David Stearns sure isn’t making many friends in New York, is he?”

“Are the Yankees really trying to cut payroll?”

The latter, naturally, is the most germane to Yankees fans. As one rival American League manager put it to Newsday: “That’s not really a thing, is it?”

It is and it isn't. But it is not yet known what that means for the winter.

During a Zoom news conference on Nov. 24, managing general partner Hal Steinbrenner spoke about desiring to drop his payroll from the 2025 figure of $319 million. Steinbrenner was not specific about how much, but certainly, if possible, to less than $304 million, the highest luxury tax threshold.

“Would it be ideal if it went down?” he said. “Of course.”

That part of his comment received far more attention than the second part. He quickly added: “But does that mean that’s going to happen? Of course not. We want to field a team we believe could win a championship.”

Last Sunday night, on the eve of the meetings, Yankees general manager Brian Cashman said he had not received marching orders to reduce payroll.

“I haven’t been told by Hal anything like that,” Cashman said.

Still, with the Yankees leaving the meetings without addressing their needs,   it is fair to wonder if Cashman is operating under, while not explicit instructions from Steinbrenner to keep expenditures down, a strong implication from above that he should do so.

The owner has been down this road before.

Multiple times before spring training 2012, Steinbrenner talked of a goal of getting his payroll to $189 million by 2014. That figure was the luxury tax threshold for that year. An oft-asked question of Cashman going into that spring training was whether it was “a goal” of Steinbrenner’s or “a mandate.”

Asked that question point-blank in early March 2012, Steinbrenner said: “I’m looking at it as a goal, but my goals are normally considered a requirement.”

Despite that kind of I’m-in-charge talk, Steinbrenner ended up OK’ing a 2014 payroll that soared  $36 million over the $189 million threshold. The Yankees paid an $18.3 million tax bill. 

The Yankees’ big outlays before the 2014 season were a seven-year, $155 million contract for Masahiro Tanaka, which worked out exceedingly well, and a seven-year, $153 million deal for Jacoby Ellsbury, which worked out exceedingly unwell (Brian McCann and Carlos Beltran also were signed that offseason).

The origin of that winter’s spending spree that relegated the “requirement” Steinbrenner spoke of to the dustbin of franchise history unquestionably was a disappointing 2013 season in which the Yankees missed the playoffs (they would miss in 2014 as well).

The question currently is just how much of an impact this past October had on the owner.

No, the Yankees did not miss the playoffs, as they did in 2013. But a four-game Division Series loss to the Blue Jays — a team Aaron Boone eloquently and accurately stated during the meetings “kicked our [butt]” throughout 2025 — was a far earlier-than-expected exit. Especially given how often Boone said he felt the “best” about this team going into October compared to the previous versions.

With the Blue Jays, Red Sox and Orioles already making big acquisitions — indications are each of those clubs will continue to be aggressive in the marketplace — the AL East in 2026 is shaping up as more stacked than usual.

Will Steinbrenner, coming off yet another disappointing October and staring down the barrel of the loaded AL East, financially handcuff Cashman, who seemed to go out of his way during these meetings to repeatedly say how many “good players” already are on the roster? Cutting payroll would further incite a fan base that doesn’t need much to become further incited.

Is Cashman already operating in those financial handcuffs?

February and spring training beckon.

What a fascinating two months to come.

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