If you’re a New York Yankees fan patiently (or anxiously) waiting to see Brian Cashman make an aggressive move this winter, you’ll be in luck very soon. The Winter Meetings begin in Orlando, Fla., on Monday, Dec. 8, and the Yankees have a history of making the most of the four-day gathering. Just ask Aaron Judge, who agreed to re-sign with the Yankees during the 2022 Winter Meetings in San Diego.
With the American League already crowded with contenders, another aggressive Yankees Winter Meetings could shift the balance of power yet again. Here’s why the rest of the AL should be paying close attention.
The Yankees have a long history of massive Winter Meetings moves
Of all the words you’re free to use when describing the New York Yankees’ Winter Meetings history, don’t even consider invoking the term “boring.” Cashman has made multiple marquee signings at the Winter Meetings, including signing aces CC Sabathia and Gerrit Cole in 2008 and 2019, respectively. We also can’t forget Max Fried, who inked an eight-year, $218 million deal during last year’s meetings in Dallas.
Cashman and the Yankees haven’t shied away from trades, either. Remember, it was at the 2023 Winter Meetings when the Yankees sent five players, headlined by pitcher Michael King, to the San Diego Padres for outfielders Juan Soto and Trent Grisham. Back in 2017, the Yankees stunned the baseball world when they acquired Miami Marlins superstar outfielder Giancarlo Stanton. And, as much as it pains us to remember how long ago this was, the Yankees landed Curtis Granderson in a three-way trade with the Detroit Tigers and Arizona Diamondbacks at the 2009 meetings.
The American League should be terrified by the Yankees’ potential plans
In a way, the Winter Meetings are the unofficial moment when the Yankees open their seemingly endless checkbook. Yes, Yankees owner Hal Steinbrenner has referenced payroll and budget this offseason, but the bottom line (pun only partly intended) is that the Yankees haven’t won a World Series since 2009. Bargain buys will not do. If Steinbrenner feels that breaking out the big bucks for Cody Bellinger, Kyle Tucker or Alex Bregman is the answer to ending one of the longest championship droughts in franchise history, then we expect to see a premier free agent introduced at Yankee Stadium later this month.
For all of the Yankees’ flaws, it’s hard to argue against the 2026 team competing for an AL East title. Judge hasn’t succumbed to the wear-and-tear yet, and Fried finished last season as one of the American League’s most valuable starting pitchers; he ranked seventh among AL pitchers with 4.4 bWAR, just behind teammate Carlos Rodón’s 4.6. While we’re not saying that the Yakees are the AL’s best team, we’re also not dismissing their World Series chances.
Now, imagine adding someone like Bregman or Tucker to an already power-heavy Yankees lineup. Bellinger thrived in his first season with the Yankees, giving Boone a reliable and durable left-handed bat. Maybe we should also prepare for the possibility of the Yankees signing yet another notable starting pitcher.
Which teams should be most concerned with the Yankees?
Let’s start with the Red Sox and Blue Jays, the Yankees’ two most significant threats to an American East title. Toronto already made a splash by signing former Padres pitcher Dylan Cease to a seven-year, $210 million contract earlier this week. As FanSided’s Robert Murray recently reported, the Blue Jays are also in on Tucker. The Red Sox have upgraded their pitching staff with the Cardinals’ Sonny Gray and the Pirates’ Johan Oviedo, though they still could benefit from another bat.
The Mariners should also be worried about the Yankees’ potential plans. Seattle came one game short of its first World Series appearance, and the Mariners have developed a championship-caliber core. If you needed any further proof that the Mariners are taking their 2026 chances seriously, keep in mind that they signed first baseman Josh Naylor to a five-year, $92.5 million contract in November.
In terms of National League teams, the Dodgers remain atop baseball’s proverbial throne, so their attention should understandably be on any organization willing to break out the big bucks for elite free agents. The same applies to the Mets, who have regularly spent big under Steve Cohen’s leadership but haven’t reached the World Series since he became owner following the 2020 season.
Who could the Yankees realistically sign at the 2025 Winter Meetings?
Our personal guess is that the Yankees will sign Bellinger and add a reliever, either via trade or free agency, during the Winter Meetings. Bellinger checks every box that the Yankees have, even after Grisham accepted the one-year, $22 million qualifying offer. We saw just how well Bellinger fit into the Yankees’ lineup last season, and he continued his recent resurgence in a big way.
We’re also keeping our eyes on former top prospect Jasson Domínguez, who struggled in the second half and subsequently saw his playing time decrease. Domínguez, who turns 23 in February, will become expendable if the Yankees re-sign Bellinger or add Tucker. Could — and would — the Yankees include Domínguez in a trade to acquire another starting pitcher, even if it’s not Paul Skenes or Tarik Skubal? Based on Cashman’s Winter Meetings history, it’s hard to put such a move against him.