It's been nearly one week since New York Yankees general manager Brian Cashman told the media he was yet to accomplish anything during this MLB offseason. The inaction since those blunt words has only served to fuel discontent with the team's passionate fan base.
Bringing Ryan Yarbrough back into the fold, re-signing Trent Grisham, and using a Rule 5 pick to bring in bullpen arm Cade Winquest are the three most prominent moves of the team's offseason to date. Yankee fans have been forced to watch their AL East rivals strengthen their rosters in hopes of improving their 2026 campaigns. The Yankees have been content to sit on the sidelines and bide their time before making anything resembling a needle-moving transaction.
Yankees need to act now with AL East continuing to bolster itself
That's a problem for a team that still has several prominent holes to fill. A quality starting pitching addition is required to protect the rotation from injuries that have already beset their top arms. The outfield is incomplete, at best, with Grisham and Aaron Judge occupying two of the starting spots. Cashman wants the media to believe they're comfortable heading into Opening Day with Jasson Dominguez and Spencer Jones, but that's a recipe for disaster in the Bronx.
The team also wants to find some right-handed pop to balance out the lefties in their batting order. It's clear Cashman needs to wake up and get to work. Here are some moves that could help the Yankees catch up to the competition.
4. Pick a big name outfielder and sign him
Kyle Tucker is the consensus No. 1 free agent in this year's class and would be a great left-handed addition to the middle of the Yankees' batting order. Unfortunately, it looks as if his contract is going to price him out of owner Hal Steinbrenner's price range.
Cody Bellinger is also going to cost a pretty penny, but the Yankees have a high comfort level with him after his excellent 2025 season in the Bronx. His left-handed swing plays well with New York's short right-field porch, but would only compound the order's dependence on southpaws.
Cashman could help allay a lot of fears by signing either of the big-name duo. Missing out on both could be answered by adding a big free agent at another spot, but landing Turner or Bellinger is the most straight forward path for Cashman to jump start the team's offseason.
3. Really roll the dice and steal Bo Bichette from the Blue Jays
If the Yankees are really serious about adding a power righty bat, then Bo Bichette might be the free agent signing that makes the most sense. He's not good enough defensively to hold down shortstop for the Yankees, but he could help them by playing second or third.
Ryan McMahon is a nice defensive option at the hot corner, but he strikes out too often to do anything more than occupy a spot in the bottom of the order. Jazz Chisholm, Jr. was excellent at second for the Yankees last year, but has seen his name continue to pop up in trade rumors. Dealing him for an outfielder or front-line starter could open up second for Bichette.
Aaron Boone expects Yankees to keep Jazz Chisholm Jr. amid trade rumors, but ‘you never know’ https://t.co/pUMHlwPn11 pic.twitter.com/RaUvdz8V01
— SNY (@SNYtv) December 19, 2025
Signing Bichette would also help the Yankees weaken a fierce rival in the AL East. He might also fall outside of Steinbrenner's ideal price range, but Cashman should be working his owner to convince him that Bichette is worth the investment.
2. Swing a trade for a starting pitcher
The Yankees continue to be linked with Japanese free agent Tatsuya Imai, but he's the only free agent hurler that makes a lot of sense for New York. That's why Cashman should dip into the trade market to fill one of his team's biggest weakness.
Tarik Skubal would be a game-changer for New York, but it's hard to envision a scenario where the Yankees match Detroit's massive asking price. Instead, look for the Yankees to look at slightly lesser options like Freddy Peralta or Sandy Alcantara on the trade market.
Any worthwhile trade will force Cashman to part with a prospect or two that he likes, but it's time for the franchise to go for it. Continuing to "prospect hug" in the coming weeks would be a great way for the Yankees to extend their World Series drought.
1. Add a big bullpen piece in Pete Fairbanks
The Yankees have watched both Devin Williams and Luke Weaver head elsewhere in free agency. In theory, that opens up some late-inning innings for Boone's bullpen.
That's why it's curious that the Yankees have not been strongly linked with former Rays' reliever Pete Fairbanks. He's just the sort of hard-throwing option the Yankees like to employ in high-leverage situations. Fairbanks is looking for a big contract in free agency, but New York should consider bringing him in to set up Davis Bednar in the eighth inning.
So what will the Yankees next move be?
The conventional answer here is to sign one of the two big outfield free agents. Instead, look for Cashman to try to beat the market by turning Chisholm into a player that better fits the team's long-term future. That move can send shockwaves throughout MLB, but could be New York's best way towards regainging the top spot in the AL East.