ORLANDO, Fla. — Before Yankees general manager Brian Cashman headed to the airport Wednesday after four uneventful days at the Winter Meetings, he spent 15 minutes discussing his week with beat writers next to the Waldorf Astoria Orlando pool.

Brian Cashman was with the New York Yankees for most of his life, but he admits he didn't think he should take the GM gig.

The always-intense rivalry between the New York Yankees and Boston Red Sox should have a little more flare in 2026 with Yankees general manager Brian Cashman calling out Sonny Gray for past comments he made about the Bronx Bombers.

But as YES Network announcer Michael Kay laid out in a breakdown on his ESPN New York show, the Yankees’ current math tells its own story — one that leaves them hovering near $300 million in payroll with almost no realistic path to adding the star power their lineup still desperately needs.

The New York Yankees need to make some big moves at the winter meetings if they want to contend for a World Series.

The Yankees have a hole to fill in left field, but according to general manager Brian Cashman, they could choose to do with internal candidates, notably Jasson Dominguez.

New York Yankees general manager Brian Cashman shared his latest update from the Winter Meetings, highlighting ongoing trade talks and challenges in negotiations with other MLB teams.

Before he went to the Mets, Devin Williams never got a formal offer from the Yankees — and never circled back to ask for one, either.

The New York Yankees are fielding calls for backup catcher J.C. Escarra, and while the team hasn’t been as active […]