Yankees Linked to Bold Trade Target as Winter Meetings Heat Up

With the Winter Meetings looming, former GMs see a bold sign-and-trade move as the Yankees unlikely path to landing a versatile Cardinals infielder.

For much of 2025, whispers around the league hinted at the Yankees eyeing Brendan Donovan. And honestly, it made a lot of sense.

The guy checks nearly every box for what New York has been missing - a left-handed bat with on-base skills, defensive versatility, and a steady presence in the lineup. But as the trade deadline approached, the Yankees went in a different direction, landing Ryan McMahon to patch up their third base situation.

Solid move, but maybe not the needle-mover fans were hoping for.

Now, a potential path to Donovan might finally be taking shape - and it’s coming from a pair of former MLB general managers who know how these deals get done.

On their Sunday SiriusXM MLB Network show, Jim Bowden and Jim Duquette both gave a thumbs-up to the fit between Donovan and the Yankees. Bowden pointed out that new Cardinals chief Chaim Bloom is actively shopping for young, controllable pitching - the kind of arms that can form the foundation of a staff.

According to Bowden, Bloom might ask for Cam Schlittler in return, but the Yankees aren’t likely to part with him. Instead, Bowden floated Will Warren as a more realistic centerpiece for a potential deal.

Let’s talk about Donovan for a second. At 28, he’s one of the most valuable Swiss Army knives in the game.

He hits for contact, plays multiple positions with ease, and still has years of team control ahead of him. In a Yankees lineup that struggled with balance, especially from the left side, Donovan’s skill set would be a welcome change.

He’s not flashy, but he’s the kind of player who makes a good lineup better - and a thin one deeper.

Of course, acquiring a player like Donovan means giving something up - and Will Warren would be no throw-in.

Warren, 26, spent the 2025 season holding down a spot in the Yankees’ rotation. He finished the year with a 4.44 ERA, a 9-8 record, and 171 strikeouts over 162.1 innings.

Not ace numbers, but certainly solid - especially when you consider the Yankees’ rotation has been held together with duct tape and hope. His fastball-slider combo gives him mid-rotation upside, and that’s exactly the kind of profile St.

Louis tends to target in these types of trades.

But here’s the rub: the Yankees are already starting 2026 with Gerrit Cole, Carlos Rodón, and Clarke Schmidt all on the injured list. That’s a lot of innings missing from the top of the rotation. So how can they afford to deal away a starter like Warren?

Bowden has a solution. He suggested that New York re-sign Michael King, who opted out of his deal with San Diego after posting a 3.44 ERA in 2025 despite battling shoulder issues. King is expected to draw interest on a multi-year deal, but bringing him back would give the Yankees a proven arm and open the door to moving Warren without leaving the rotation too thin.

Then there’s the Ryan McMahon angle. The Yankees brought him in to stabilize third base, but both Bowden and Duquette believe Donovan is simply the better all-around player.

If the Yankees can land Donovan, they’d have the flexibility to slide McMahon into a bench role or even explore flipping him elsewhere. That kind of versatility - both on the field and in roster construction - is exactly what this front office has been chasing.

Bottom line: if the Yankees can pull this off, it’s a move that could quietly reshape the roster. Donovan wouldn’t be the loudest acquisition of the offseason, but he might end up being one of the most impactful - especially for a team that’s trying to find balance, depth, and durability heading into a season full of question marks.