The Athletic's Yankees insiders predict blockbuster trade with Cardinals this winter

The Yankees' makeover must extend beyond free agency.

St. Louis Cardinals v Arizona Diamondbacks
St. Louis Cardinals v Arizona Diamondbacks / Christian Petersen/GettyImages

Have you checked out the free agent pool of game-changing offensive talent this winter? Pretty bleak! Unless you're paying Cody Bellinger $200 million -- and the Yankees very well might be doing that -- there might not be a true radical in the bunch.

If the Yankees are going to navigate this offseason and return immediately to contention, they're going to need -- gulp -- Brian Cashman to show off his stuff on the trade market. And he's going to have to give to get.

He's going to have to strip himself of the overwhelming desire to "win" every trade in the press the next day. It might cost top-tier, even big-league talent, to get the offensive boost (from the left side of the plate, please, please, please) that this Yankees team needs. He can't be afraid to give up 26-man roster members for a shot at filling holes. Goodness knows he's lost enough trades already by trying to be cautious. It might be time to throw that caution to the wind.

And, whenever he's ready, the St. Louis Cardinals are right there.

The last time these two sides linked up, it was for one of Cashman's more daring experiments, and he earns kudos for trying something even if "Jordan Montgomery for Harrison Bader" ended up hitting every possible end of the trade grade spectrum. It helped kill chemistry in the Bronx. It added an elite center fielder in a walking boot. Montgomery started hot in The Lou. Then he slowed down? Then Bader almost singlehandedly carried the Yankees to the ALCS? Then the Cards lost so much they rented Monty to the Rangers, while Bader missed several different chunks of the 2023 season as the Yankees sputtered? Lots to process here. Some of it very good!

That trade came about because St. Louis craved pitching and Mike Maddux believed he had a fastball-centric solution to Montgomery's mid-rotation woes. This winter, the Cardinals have the same need and the Yankees have the same surplus. That's why The Athletic predicts New York will come calling about one of St. Louis' many utility players, dangling some of their MLB depth arms in exchange.

Yankees-Cardinals Trade Rumors: Which arm for Brendan Donovan?

According to Chris Kirschner, Brendan Donovan is the potential Cardinals target with the highest ceiling; his season ended early due to elbow surgery, but he posted a .785 OPS, hitting .284 with a .365 OBP from the left side. He covered left, right, second, third and first, doing his best work in 13 games at first base (1.145 OPS). Savant grades him out, as expected, as a powerful xWOBA guy with a keen batting eye who provides excellent offensive value.

What'll it cost the Yankees to add a player under control through 2027? Expect a full-time rotation member, eg Clarke Schmidt or Michael King, to start the package. Schmidt, coming off a career high in innings (by far) would certainly be the pitcher the Yankees would rather move, but it doesn't always work that way. Clayton Beeter found his way into Kirschner's rumor, and it probably won't be the last time the potential tweener/strikeout artist gets shopped around.

The third piece of this deal will hurt -- Kirschner pitched Randy Vásquez, and Jhony Brito should be on the table -- but that's probably how the Yankees will have to differentiate their offering. They have plenty of pitching on the verge of cracking the big-league depth chart, as well as a few nasty righties who already have. They need offense from the left side wherever they can get it -- and that "wherever" will probably be St. Louis. There are plenty of paths here, and it's now on Cashman to thread the needle effectively.