Yankees Haven't Made Major Transaction Since July

The New York Yankees were embarrassed by the Toronto Blue Jays in the American League Division Series, nearly getting swept on their home turf in the Bronx, were it not for the heroics of captain Aaron Judge. His home run ball barely remained fair, and that kept the season alive, despite another unceremonious postseason effort by Carlos Rodon.

You would think that, between the two teams, it was the Blue Jays who were flummoxed in Toronto, given their busy off-season. When you have the Jays smoking stogies on River Avenue like they are Canadian William Hickeys in "National Lampoon's Christmas Vacation," you hope for more to kick off a winter. Instead, Toronto has been active and want to head back to the World Series.

The Toronto Blue Jays celebrate at Yankee Stadiu — Oct 8, 2025; Bronx, New York, USA; The Toronto Blue Jays celebrate after beating the New York Yankees to win the ALDS round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

This winter, Toronto added Dylan Cease, whom they hope to mold into the next Kevin Gausman, aiming to help him reach a new level in his career. Just replace that wicked splitter with a devastating fastball and a handlebar mustache.

The Jays also added New York Mets deadline addition Tyler Rogers, as well as Cody Ponce, who came from playing across the Pacific last season. They may add Kyle Tucker as well. The two have been linked all winter.

How Many Days Since the Last Yankees Transaction from Outside the Organization?

Thus far, the Yankees have been quiet. There is still a ton of time left to make moves, but as 2026 has dawned, 155 days have passed since the organization added an impact player from outside. After the Yankees acquired rockstar closer David Bednar from the Pittsburgh Pirates for a slew of catching prospects in Rafael Flores and Edgleen Perez, and outfielder Brian Sanchez, their transaction line has gone dormant.

Aug 16, 2025; St. Louis, Missouri, USA; New York Yankees relief pitcher David Bednar (53) pitches against the St. Louis Cardinals during the ninth inning at Busch Stadium. Mandatory Credit: Jeff Curry-Imagn Images | Jeff Curry-Imagn Images

Numerous holidays have passed since the Bednar deal. Labor Day, Halloween, Veterans Day, Thanksgiving, Christmas, and New Year's have all come and gone, and the organization still has not even gone out and landed its prize target, which is speculated to be Cody Bellinger. Bellinger had a stellar year in New York on both sides of the ball, but his agent, Scott Boras, and the Yanks are currently in a stalemate.

Even if they do sign Bellinger, it is not like he is a new bat. The Yankees are still running it back.

Hal Steinbrenner Told Us How Things Will Go

The tea leaves have been there all winter, too. Jack Curry did not offer any promising information about Tatsuya Imai, who has now signed with the Houston Astros. Then there was Hal Steinbrenner's quibbling about monetary matters even before that. Steinbrenner lamented the luxury tax bill as well as what he owes the city every winter for his stadium, which he regularly sells out, or at least comes close to night in and night out.

"That's not a fair statement or an accurate statement," Steinbrenner said, according to Bryan Hoch of MLB.com. "Everybody wants to talk about revenues. They need to talk about our expenses, including the $100 million expense to the City of New York that we have to pay every February 1, including the COVID year. So it all starts to add up in a hurry."

New York Yankees owner — Dec 21, 2022; Bronx, New York, USA; Hal Steinbrenner during a press conference at Yankee Stadium. Mandatory Credit: Jessica Alcheh-Imagn Images | Jessica Alcheh-Imagn Images

Steinbrenner, who has never had the everyman personality his father did, buried himself in that media presser, but in a way, it could have been foreshadowing for this off-season. Nobody expects the Yankees of old at this point. This is still unacceptable, and hopefully it changes by the time the team breaks for camp after Valentine's Day. Another holiday cannot pass without the Yankees adding a new player.

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