Predicting where each Yankees free agent will sign in 2024

The New York Yankees will be losing 150 pounds of dead weight off their 40-man roster over the course of the next few weeks. Now, all that's left is to pose with the gigantic jeans they used to wear, then get back to filling 'em with better talent.

The offseason begins in earnest five days after the World Series wraps, and the non-tender deadline is Nov. 17. That represents the first demolition day, where veterans like Kyle Higashioka and Jonathan Loaisiga might join the minor-league flyers and expiring big-league contracts on the free agent market.

Then, it's time for the Yankees to really get down to brass tax -- or, more specifically, it's time for the rest of the league to feast their eyes on the free agents who are escaping New York's clutches. Harrison Bader got an early start in Sept., and no longer qualifies as a forthcoming Yankees free agent following his short stint on the Reds as part of Waiver-Palooza 2023.

Now, it's time for the rest of the team's birds to leave the nest -- and, yes, it really seems as if every single free agent in the Yankees' 2023-24 class could be finding a new home soon. Captain Aaron Judge did say big changes are needed, and when he talks, Hal Steinbrenner and Co. typically listen (via a long-distance call from Rome). The fewer members of last season's 82-80 team who return, the better.

Predicting where Yankees free agents will sign during 2024 Winter Meetings, before regular season

Isiah Kiner-Falefa: Pittsburgh Pirates (Two Years, $14 Million)

Where does Isiah Kiner-Falefa belong? A player best cast in multiple roles, with 100+ games of experience feeling like the sweet spot. A player willing to take on whatever is thrust upon him, but who doesn't perform to his capacity when too much is thrust upon him. A player who probably will receive a multi-year commitment, but perhaps hasn't earned one? A Gold Glove third baseman who wound up anywhere but that position at his previous stop.

Yeah. Pittsburgh, or another young team trying to make the leap to 80-or-so wins, feels like the correct landing spot.

IKF played a relatively competent left field and completed circuitous routes in center this past summer, but belongs in the infield (and in a mentorship role for a team that requires glue). He'll be missed, and he'll miss the Bronx, but a team with expectations like the Yankees could probably do better than a 78 OPS+ on their bench (though they certainly didn't last year).

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?

Frankie Montas: St. Louis Cardinals (Two Years, $22 Million)

That said, I fully acknowledge that the Yankees will swim in these Montas-infested waters if his price remains low enough that a one-year bounce-back is his only option.

With a few weeks to stew on things, though, it really feels as if a pitching-desperate team will be willing to go further than the Yankees in this market, even though it was New York that helped rush Montas' rehab so that he could pitch one very strange game at the big league level this season. There's another team I believe could get involved, but I've chosen them as a destination for a different embattled Yankees righty.

Montas, at his peak, was the kind of right-hander a team stakes their entire trade deadline upon (if they're unwilling to, say, surrender Anthony Volpe in exchange for Luis Castillo). Unfortunately, the Yankees never actually saw him at his so-called peak; his shoulder was already beefed upon acquisition and in need of repairs, which didn't come until well into the righty's prep for 2023.

If Brian Cashman can secure him as a fifth/sixth starter on a bargain deal for 2024, so be it. Worse things have happened. But someone has to go two years ... right?

Wandy Peralta: Miami Marlins (Two Years, $18 Million)

Alright ... so ... the gnarly truth is that a two-year deal for Peralta is far more dangerous than a one-year deal for Middleton, especially given the 32-year-old's metrics, which could explode at any moment.

There's a chance that the funky left-hander is the Reverse Andrew Heaney, and that no matter what his FIP, spin and walk rate say he should be, he'll always manage to come out on top anyway. Unfortunately, it's far more likely that regression is nigh, and the Yankees are lucky it didn't really come in the second half of 2023 after they opted not to shop Peralta at the deadline.

So, what's a team that fancies themselves a bit more central to the narrative than the rest of the world does entering 2024? The Padres are looking to cut payroll, not add it in the bullpen. The Detroit Tigers make some sense, but they're probably still a year away from making moves like this. A return to the San Francisco Giants is a fun thought, but they're the ones who didn't trust Peralta's development in the first place (or truly coveted one year of Mike Tauchman).

We're going with the NL Wild Card team that embraces funk, but probably has a heightened sense of themselves after living through remarkable one-run game luck in 2023. Like Peralta, they survived an impending regression that never came. Now, someone besides Kim Ng will be calling the shots, and that person will presumably be instructed to treat the Marlins like a team that really belonged in the playoffs and must continue to chug forward.

Peralta might be extremely fun in Miami. Here's hoping he's able to continue to fulfill his duties, even though the underlying numbers are coughing loudly and daring you to notice.