Major League Baseball’s Winter Meetings are underway, and over the next four days, MLB executives, insiders, reporters, and others will gather. It is expected that some of the biggest offseason moves will take place this week. For the New York Yankees, their front office is under a microscope, and it’s time that Brian Cashman and the rest of the Yankees ‘ executives get going this winter.
Other AL East clubs like the Blue Jays, Red Sox, and Orioles have already made big moves, while the Yankees have been quiet. Last year, during the meetings, New York signed Max Fried to his monster contract. Here are three moves the Yankees must make this week to improve their roster.
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Yankees Need to Re-Sign Cody Bellinger
This should be priority number one for Casham and the Yankees. Cody Bellinger had a stellar 2025 campaign, hitting 29 home runs and driving in 98 runs. Bellinger looked comfortable in pinstripes, can play all three outfield positions, and the Yankees can not allow another team to outbid them for Cody Bellinger.
His swing plays well in Yankee Stadium, and the Yankees should do everything in their power to work out a deal. Bellinger is likely worth an AAV contract of $30 million, or potentially more, but the next question will be how many years an MLB club is willing to commit to the 30-year-old.
GettyYankees linked to acquiring trio of players from Cardinals.
Trent Grisham accepted his qualifying offer to stay with the Yankees, but if the Yankees don’t re-sign Bellinger, there will be a big hole in the outfield.
Trade For MacKenzie Gore
This should be item number two on the Yankees’ front office’s mind over the next few days. Nationals‘ starter MacKenzie Gore has been one of the big arms floating around on the trade market, and considering New York’s injured rotation at the moment, they could use a pitcher to hold over some innings until Gerrit Cole and Carlos Rodon return healthy.
MacKenzie Gore was an All-Star in 2025 and posted a 4.17 ERA over 30 starts and 159.2 innings. He also struck out 185 batters. If the Nationals don’t want to make a deal for Gore, New York could target other starting pitching options on the trade market, like Mitch Keller or Joe Ryan.
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Sign Edwin Diaz to Fill the Closer Role
This would be big news across MLB, but the truth is the Yankees are now in the market for a closer after losing Devin Williams to free agency, and Luke Weaver is still deciding who his next team will be.
After the Mets signed Williams to a three-year, $51 million deal, the Yankees have the opportunity to one-up their cross-town rival and poach away their three-time All-Star Edwin Diaz. Diaz recorded 28 saves in 2025 and posted an ERA of 1.63 in 66.1 innings.
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