Predicting where each Yankees free agent will sign in 2024

Keynan Middleton: Chicago Cubs (One Year, $9 Million)

The Astros would be all over Middleton on a three-year deal if Jim Crane was still callin' the shots like last winter, but they have a GM in place now, so that's over with. Perhaps the correct answer here is "anywhere but the White Sox," the team with the rippable culture that he torched in the aftermath of his trade to the Yankees last summer.

In reality, any team with a moderate amount of money that believes there is no such thing as a bad one-year deal should be willing to finance Middleton's next contract. The erratic righty harnessed his stuff for long enough to whiff 64 men in 50.2 innings in a contract year, finishing the season with a 3.38 ERA combined between his two stops. His time in New York, sandwiched around an injury, was pretty great! He posted a 1.88 ERA in 14.1 innings, striking out 17 in the process.

Typically, the Yankees would try to extend their midseason trade acquisitions to "make sure" they get as much out of them as they possibly can. Middleton? It's possible, but they fundamentally understand how to develop a relief corps, and probably don't feel the need to double down here. A team on the verge of the postseason with a sizable budget and the ability to withstand a potential implosion, if the contract doesn't work out. That would be the Cubbies, who won't match Cody Bellinger's forthcoming contract and have some budgetary wiggle room. Plus, he hates the Southsiders. What's not to like?