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Yankees 2025 Winter Meetings preview

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This story was excerpted from Bryan Hoch’s Yankees Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

NEW YORK — There has been a fair amount of hand-wringing in recent weeks about the Yankees’ payroll, fueled by managing general partner Hal Steinbrenner’s remark that it would be “ideal” to come in lower than last year, when the club spent $319 million on a roster that won 94 games before bowing out early in October.

Yet these are still the Yankees, a team that can turn its wallet into a weapon. Opposing general managers know it, and so do agents. When Brian Cashman was asked recently if he’d be willing to add another nine-figure contract, the veteran general manager grinned.

“I would always do that,” Cashman said. “I’m good at spending money.”

But there’s still much more to do.

“We had a good team last year,” Cashman said, “but it’s not the same team because of free agency. We’ll see where it all takes us.”

Though Cashman mentioned free-agent starter Michael King among the early calls he’s made, the primary focus appears to be in the bullpen. That group was uneven this past season, and free agency has already pulled Devin Williams and Luke Weaver to the open market.

The Yanks have voiced interest in re-signing Cody Bellinger, valued for his athleticism and versatility, though he’ll have no shortage of suitors coming off a strong season. They’ve also touched base with the representatives for Kyle Tucker, rating Bellinger and Tucker as the best available free-agent outfielders.

Infield help could be on the radar with Anthony Volpe set to miss the start of the season; as currently built, they’d have José Caballero or Oswaldo Cabrera as the Opening Day shortstop.

Potential Trade Candidates

Here’s a wild thought if the Yanks want to shake things up: Jazz Chisholm Jr. is entering his final season before free agency, and they’ve been lukewarm toward the suggestion of a contract extension. Coming off a season in which he belted 31 homers and stole 31 bases, Chisholm could bring a significant return.

A more realistic path could involve Jasson Domínguez or Spencer Jones, depending on how their pursuits of Bellinger and/or Tucker work out. Domínguez hardly played during the second half of last season, and no one benefits from having him ride the pine again.

It’s a similar story with Jones, who hit 35 homers with a .933 OPS last year in the Minors. There’s still swing-and-miss in his game (179 strikeouts in 438 at-bats), but Cashman admitted Jones would’ve already made his debut if he was with another organization.

Carlos Lagrange (No. 2) jumped in the prospect rankings this past season on the strength of a campaign in which he was 11-8 with a 3.53 ERA in 24 Minor League games (23 starts), striking out 168 batters in 120 innings.

A $10,000 find out of the Dominican Republic, the 6-foot-7 22-year-old right-hander hits triple-digits with his fastball and has improved his control. He could follow a trajectory similar to Cam Schlittler, whose strong second half included a dominant outing to eliminate the Red Sox from the American League Wild Card Series.

Aaron Judge has captured three of the last four American League MVP Awards, establishing himself as one of the most dangerous right-handed hitters the sport has ever seen. He is also the reigning batting champion. And when he says he would trade all of it for a World Series ring, it rings true.

After matching the Blue Jays for the AL’s best win total at 94, there is a temptation inside the organization to bring back most of the 2025 group. Club officials believe the gap between the Yankees and Toronto — along with the Dodgers, now back-to-back champions — is smaller than most outsiders think.

Do they actually have enough to reward Judge’s prime with a title? That will be the question hanging over everything they do in Florida.

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