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Yankees general manager Brian Cashman expects to be busy at the upcoming MLB Winter Meetings in Orlando.

The 2025 MLB Winter Meetings are just about here, and MLB insider Jim Bowden of The Athletic believes the New York Yankees will have the No. 1 available free agent on their team by the time the annual Orlando, Florida-based event ends.

Bowden predicted the Yankees to land free agent outfielder Kyle Tucker on a 10-year, $427 million contract over the next week as one of the deals he’d like to see happen.

Tucker spent 2025 with the Chicago Cubs and slashed .266/.377/.464 with an OPS+ of 143 and 22 home runs and 73 RBIs in 136 games. Those numbers are among the worst in a single season for the soon-to-be-29-year-old.

Jim Bowden Predicts Yankees Will Announce Kyle Tucker Signing Next Week

Tucker has been a nemesis of the Yankees and fans due to his seven-year run with the Houston Astros. He helped eliminate the Yankees twice in the ALCS, most recently in 2022 when Houston swept the Yanks.

But with a hole to fill in left field — even though Tucker is a natural right fielder — the Yankees could open their wallets to lock in a five-tool, left-handed outfielder to complement two-time-reigning American League MVP Aaron Judge.

“As long as Tucker is willing to play left field, I think he’d be the perfect fit at Yankee Stadium for the next decade,” Bowden wrote Friday. “He’s a five-tool player who does everything above average. He’s not a face-of-the-franchise type but they don’t need him to be because they already have Aaron Judge.”

Tucker would replace Cody Bellinger in left field, who is also a free agent. The Yankees pivoted to Bellinger — and have room to sign Tucker — after Juan Soto spurned them to sign with the New York Mets on a 14-year, $765 million contract last offseason.

“That contract may seem like a lot of money,” Bowden wrote. “But think about it this way — it’s a savings of $338 million over what Juan Soto was paid last offseason.”

Jim Bowden Predicts The Yankees To Land Edwin Diaz Too

Soto isn’t the only free agent to depart across the Whitestone Bridge to play for the Mets. Clay Holmes and Devin Williams — the Yanks’ opening-day closer in each of the past two seasons — signed free-agent deals with the Mets, most recently Williams’ three-year, $50 million contract last week.

But Bowden is predicting the Yankees to turn the tables on their crosstown rivals and lock in All-Star reliever Edwin Diaz on a five-year, $88 million deal.

“The Subway Series gets a new twist, as the New York teams swap closers,” Bowden wrote. “The Yankees take a risk with a five-year deal for a reliever but the immediate boost to the back end of their bullpen will be significant.”

Diaz will turn 32 in March and is coming off another dominant year where he posted a 1.63 ERA and locked down 28 saves. He would help general manager Brian Cashman fulfill his goal of remaking the Yankees’ bullpen, with Diaz joining 2025 trade-deadline-acquired relievers David Bednar, Camilo Doval and Jake Bird.

Bowden also floated the Yankees landing starting pitchers Sandy Alcantara from the Miami Marlins and Freddy Peralta from the Milwaukee Brewers to bolster their rotation and two-time NL Silver Slugger Ketel Marte from the Arizona Diamondbacks.

Pat Pickens is an experienced sports writer and media personality who has written for outlets like NHL.com, the Associated Press, the New York Times and USA Today. He covers the NFL, NBA, NHL and NBA as a breaking news contributor at Heavy. More about Pat Pickens

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