Predicting destinations for Yankees' 2023-24 free agents (and 1 they should bring back)

The New York Yankees have a robust free agent class this winter. Will they mess with any of them?

Houston Astros v New York Yankees
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Welcome to Yankees Free Agency! Probably two or three months sooner than you wanted to arrive here, but hey, we welcome you nonetheless.

The Yankees have stretched their (fake, completely fake) budget to its furthest reaches this season, and because they opted out of moving anyone at the deadline, they'll pay the Steve Cohen Tax next season. Why did they do that? If there's anything the modern Yankees love, it's Budget. They betrayed their own line in the sand by not selling one measly little guy! Weird! What is this team's code of ethics and operations? Simply ... what?!

I digress. That means that next year, they'll pay a significant tax, but they will get a good deal of money off the books, too. Last winter was the Offseason of Aaron Judge. Either the Yankees would choose to pay him a massive sum, or they'd pass and watch their roster wilt (or he'd spurn them and become an arsonist). As far as offseason decisions go, it was a massive one.

This time? They're losing a lot of cash guaranteed, with several players who almost definitely will not re-sign hitting the open market. Of the Yankees' group of free agents, only two seem likely to return in any capacity (and maybe only one should).

In the interest of clearing cash, these are our best way-too-early predictions for these players' future landing spots, as well as some projected contracts before the market opens. It seems as if the Yankees will lose at least ~$45 million from their 2023 payroll before shuffling anything around. It's not, say, "shedding the entire Giancarlo Stanton/DJ LeMahieu contract" good, but it's still pretty impactful.

Predicting new homes and contracts for Yankees' 2023-24 free agents

The Absolute Nos: Josh Donaldson, Luis Severino

Do we really need to discuss Josh Donaldson any further? If the Yankees pick up his mutual option for 2024 -- especially after he flaunted their 60-day IL placement with his recent public BP session -- you'll have to also pick up ... my jaw from the ground three floors below (it broke through the floor of my apartment by falling with the sheer force of a jackhammer).

Extending the qualifying offer to Luis Severino in hopes of recouping a draft pick would be exceptionally risky. After the season he's had, he'd probably accept a one-year, ~$18 million to rebuild his reputation again, even if he's grown out of love with the Yankees. The Yankees should not consider a multi-year deal here, no matter the cost.

Catcher David Freitas is listed on Spotrac's group of contracts, but he's on the Triple-A Oklahoma City Dodgers. The Yankees probably don't have much of a say in his offseason, but I personally hope he has a nice one!

The "Maybe, But Probably Nots": Keynan Middleton

Hey, let's see what the rest of his season looks like! The Yankees traded for him for a reason. That said, he's a fifth-or-sixth-or-seventh reliever. New York prints relievers. Using their budget on Middleton doesn't sound wise.

Free Agent: Frankie Montas

Prediction: Cardinals, One Year/$10.5 Million

A team in need of starting pitchers with All-Star upside at a mid-to-low-tier price will surely jump at the chance to pay Montas a one-year contract and facilitate his bounce back (while crossing their fingers).

Honestly, there was a time just a few weeks ago when I would've said ... the Yankees should consider it. After all, they targeted him for a reason, and a healthy Montas has always been a game-changer at every stop. As his price dropped precipitously during a year away from the game, it seemed like a new deal could provide significant bang for the team's buck (or a moderate sunk cost, at worst).

Then, Montas shut down his throwing program (again) and has gone radio silent in the weeks that have followed New York's trip to Anaheim. Accruing pitching depth will be crucial once more this offseason, as the Yankees lose Severino from their projected rotation (and can't exactly bank on contributions from Carlos Rodón). It's a better idea if that depth is reliably healthy, though. Someone will value Montas (Cards? Angels? Dodgers?) at a price the Yankees don't.

Free Agent: Wandy Peralta

Prediction: Cubs, Two Years/$15 Million

Wandy Peralta, a 32-year-old left-hander, has earned a raise on his $3.35 million salary based on his body of work. He's proven himself in the postseason with the Yankees, taking over five consecutive ALDS games in 2022. He's been killer on lefties in 2023, holding them to a .119 average and .170 slugging through play on Aug. 8.

Unfortunately, his control has deserted him a bit. His expected statistics indicate regression is coming (after all, his lefty success seems a little unsustainable). He's escaped plenty of jams. Hopefully, for Peralta, the reckoning doesn't come before he can cash in.

Those metrics aren't a secret, though. Cautious, analytically-driven teams might shy away from committing multiple seasons to someone who could be on a cliff's edge. The most likely teams to sign Peralta are borderline contenders who are about to commit to full bullpen overhauls. Remember when the Red Sox signed Joely Rodriguez this offseason? Exactly. The Cubs, or someone like them, will probably find Peralta more appealing than the Yankees, though we wish him well.

Free Agent: Harrison Bader

Prediction: Yankees (But Maybe They Shouldn't...), Three Years/$48 Million

At this price, the Yankees should consider re-upping with Bader, even though his injury history could bite them in the years to come. While the bat has been occasionally potent and clutch, speed and defense are his true calling cards, and those don't typically increase after a player reaches 30.

If Bader requires a four-year commitment, despite his recent stumbles, or more money? The Yankees should walk away and thank the Bronxville native very much for an enjoyable year.

It's all about the hometown discount in this particular conversation. If Bader wants to offer one -- and maybe he should -- there could be some middle ground to be found. The Yankees have Spencer Jones, Jasson Dominguez and Everson Pereira incoming, but they have an insane dearth of big-league outfield depth at the moment. Sending your most athletic big-league outfielder to the curb is a bold move (even if it makes solid sense).

Whatever this conversation ultimately turns into, the Yankees should absolutely extend Bader the qualifying offer. If he wants to run it back for a prove-it year, at a similar price to what his extension might cost per season, that would be a good fit for both sides.

Free Agent: Isiah Kiner-Falefa

Prediction: Yankees, Two Years/$16 Million (And Why Not?!)

Momentum is brewing for the New York Yankees to re-sign Isiah Kiner-Falefa to shore up their utility spot for the next few seasons, and you know what?! We couldn't be happier.

After a turbulent season where Kiner-Falefa was miscast as a starting shortstop and struggled to find grace, he's been far more valuable as a super utility option (though he, uh, shouldn't play nearly as much outfield in the future). Last season, when he was tougher to love? 85 OPS+. Season before that? 85 OPS+. 2020? 93. 2023, so far? 93. IKF is nothing if not consistent, which is easier to appreciate when he's flitting around the diamond than when he's clogging up the shortstop spot.

He was unfairly treated as a stand-in for Corey Seager and Carlos Correa. Now? He's Luis Sojo, and he's nailing it. Much better.

The Yankees were willing to commit $6 million to IKF in 2023 before he'd shown much promise. Why wouldn't they be willing to commit $8 million to him next season now that he's proven to be a nice piece of glue to a downtrodden roster?

He shouted, "Thank God I'm a Yankee!" after the deadline passed without him being shipped out this summer. Who else on the current roster would even consider saying that?! He fits like a glove in his current role and he wants to stay. It would be nice to see something cost-effective work out to maintain a sliver of continuity on a roster that needs a pretty big overhaul.

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