What Yankees fans need to know

What Yankees fans need to know

Tis the season to go shopping, and that applies to Major League Baseball.

General managers, executives, agents, media and more are on their way to Nashville, Tenn., where the Winter Meetings begin Sunday at the Gaylord Opryland Resort & Convention Center. While nothing is guaranteed, the annual gathering is the perfect time for splashy free agent signings and blockbuster trades.

The Yankees, trying to correct course after a disappointing 2023, will be active over the next few days, even if no moves are announced. Here’s what their fans need to know as the baseball world converges on The Volunteer State.


This is a critical winter for the Yankees, as they are fresh off an 82-80, fourth-place season that saw them miss the playoffs for the first time since 2016.

Brian Cashman and Aaron Boone were under fire before that, but both remain. Meanwhile, the team hasn’t publicly dismissed any high-ranking executives or coaches despite Hal Steinbrenner’s assurances that changes are coming.

The most notable tweaks should be to the roster, and the Yankees are expected to be big-game hunters as the Hot Stove heats up. While it remains to be seen how much money Steinbrenner is willing to spend, it’s clear the Yankees need to upgrade if they want to bounce back in 2024 and avoid a 15-year championship drought.


Cashman made it clear at the GM Meetings that the Yankees need two outfielders for center and left. One has to hit lefty, but two wouldn’t hurt a lineup that always seems to be lacking port-side balance.

Cody Bellinger, a center fielder, is the best free agent hitter available not named Shohei Ohtani, who doesn’t look like a match for the Yankees. Bellinger comes with risk, but the former MVP enjoyed a resurgence with the Cubs in 2023. Secondary free agent targets for center could include the veteran Kevin Keirmaier and KBO star Jung Hoo Lee.

As for trade targets, the Yankees will surely try to pry Juan Soto away from the Padres during the Winter Meetings. The superstar left fielder won’t come cheap, though.

The Yankees could also engage the Cardinals, who have a surplus of controllable players who can hit lefty and play the outfield.

Cashman has also said that he’s in the market for starting pitching after the Yankees’ rotation, aside from Cy Young winner Gerrit Cole, fell apart in 2024. They should be serious players for Japanese ace Yoshinobu Yamamoto, though his sweepstakes won’t wrap until after the Winter Meetings, according to SNY’s Andy Martino.

Secondary pitching targets via free agency could include Shota Imanaga and reunions with Jordan Montgomery and Frankie Montas. It also wouldn’t be a surprise to see former Cy Young winners Shane Bieber and Corbin Burnes on the trade block.

While outfielders and starting pitching are the priorities, the Yankees could also upgrade at third and beef up their bullpen.


The Yankees have a handful of major league-ready players they can trade, including starters Clarke Schmidt, Michael King, Jhony Brito and Randy Vásquez; catchers Kyle Higashioka and Ben Rortvedt; second baseman Gleyber Torres; and young outfielder Everson Pereira.

Top farmhand Spencer Jones, an outfielder, could be the centerpiece for a big return, as could pitching prospects Chase Hampton, Drew Thorpe and Will Warren. Clayton Beeter, another hurler, may be dangled as well.

With Anthony Volpe and Oswald Peraza having already begun their MLB careers, shortstop prospects George Lombard Jr., Roderick Arias and Trey Sweeney are also expendable talents.


The Yankees entered the offseason with seven free agents: Montas, Luis Severino, Isiah Kiner-Falefa, Wandy Peralta, Keynan Middleton, Luke Weaver and Zach McAllister. Domingo Germán, Lou Trivino, Franchy Cordero, Albert Abreu, Ryan Weber, Anthony Misiewicz, Jimmy Cordero, Matt Bowman and Billy McKinney have since joined that group.

Montas, Peralta and Middleton are among those who could return, while Severino agreed to a deal with the Mets on Wednesday.

The Yankees have also traded Jake Bauers to the Brewers, signed reliever Yerry De Los Santos and claimed Oscar Gonzalez off waivers since the offseason began.


The Winter Meetings aren’t only about free agency and trades.

The 2024 MLB Draft lottery will take place on Tuesday. Non-playoff teams are entered into the lottery for the top six picks. The Yankees have a 0.6% chance of being in the lottery. However, if they don’t get a top-six pick, their first overall pick will drop 10 spots since they exceeded the competitive balance tax’s second threshold. If the Yankees do get a top-six pick, their second-highest selection will fall 10 spots.

The Rule 5 Draft will then take place on Wednesday. The Yankees recently protected Beeter and Agustin Ramírez from the draft by adding them to their 40-man roster.

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