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What's Next for Yankees in Free Agency and Trade Market After Aaron Judge Megadeal?

Joel ReuterDecember 7, 2022

Aaron Judge
Bob Levey/Getty Images

A 99-win season and sixth straight playoff appearance is a successful season for most MLB franchises, and re-signing the reigning MVP is almost always a reason to celebrate, especially when he's the homegrown face of your franchise.

However, the New York Yankees aren't most franchises, and simply bringing back Aaron Judge—a move reported by MLB Network's Jon Morosi on Wednesday—to a flawed roster that was exposed in October is not going to cut it.

"I think they understand that the 13-year championship drought feels like about 130 years in Yankee land, and I think there's more to come," MLB insider Mark Feinsand said on MLB Network on Wednesday morning.

The last time the Yankees went at least 13 years without winning a ring were some of the leanest seasons in franchise history. They reached the playoffs just three times in 17 campaigns between titles in 1978 and 1996, and outside Don Mattingly, not much went right during that time.

When they finally came out the other side of that dry spell, they kicked off a bona fide dynasty, winning four rings in five years.

The question now: What do the Yankees need to do to set themselves up for similar success with Judge back in the fold?


1. They Need 1 More High-End Starting Pitcher

Carlos Rodón
Joe Sargent/Getty Images

The high-end shortstop market has grabbed headlines this offseason, but starting pitching has been the fastest-moving market by far.

Here's a look at all the starting pitchers who earned a spot among the top 50 free agents at the start of the offseason, according to MLB Trade Rumors:

Carlos Rodón
Jacob deGrom
Justin Verlander

Koudai Senga
Chris Bassitt
Jameson Taillon
Taijuan Walker

Sean Manaea
Andrew Heaney
Noah Syndergaard
Nathan Eovaldi
Clayton Kershaw
José Quintana
Zach Eflin

Tyler Anderson
Ross Stripling
Michael Wacha
Corey Kluber
Drew Rucinski

Seeing all of those names already crossed off should tell you all you need to know about the sense of urgency with which the Yankees need to approach upgrading their starting rotation if they intend to do so via free agency.

The early reports are that they are aiming high and aggressively targeting Rodón:

Jack Curry @JackCurryYES

Now that Judge has been secured, what’s next for the Yankees? They have definite interest in Rodon. They feel that Rodon has the mettle to succeed in NY. A tough, talented lefty at the Stadium would be a nice fit.

The great unknown of this year's market is right-hander Koudai Senga, who has been one of the Japanese League's top pitchers for several years. It's always a bit of a crapshoot projecting how a player's game will translate to the majors, but his 2022 numbers are tough to ignore. The 29-year-old had a 1.89 ERA, 1.04 WHIP and 159 strikeouts in 148 innings in 2022. He won't be subject to the posting system, so he's free to sign anywhere this offseason.

Beyond those two, grizzled veteran Corey Kluber might be the best target. With his experience and track record of postseason success, there is little doubt he would be able to handle the pressures of pitching in Yankee Stadium—where he called home in 2021 and where he sports a 3.04 career ERA.

If free agency doesn't prove to be the answer, the Yankees could also turn their attention to the trade market.

The Milwaukee Brewers are one hypothetical trade partner, not because they are not expected to contend in 2023, but because it's unlikely they will be able to afford both Corbin Burnes and Brandon Woodruff long term, as both will be free agents after 2024. However, the Brewers have already indicated they don't intend to move either starter, per USA Today's Bob Nightengale.

The more likely trade partners are the Miami Marlins, who have a wealth of young, controllable starting pitching and have indicated their willingness to listen to offers on anyone besides NL Cy Young winner Sandy Alcantara, per the New York Post's Jon Heyman.

The Yankees' best target in terms of acquisition cost, likelihood of a deal getting done and expected production is Pablo López. The 26-year-old is controllable through the 2024 season, and he posted a 3.75 ERA, 1.17 WHIP and 174 strikeouts in a career-high 180 innings in 2022 while serving as Miami's No. 2 starter.

The Marlins have reportedly shown interest in veteran third baseman Justin Turner in free agency, per the Miami Herald's Craig Mish, so perhaps they would have similar interest in Josh Donaldson if the Yankees were to absorb some of his salary.

How about this for a hypothetical deal:

  • To NYY: RHP Pablo López
  • To MIA: 3B Josh Donaldson, SS Oswald Peraza, RHP Yoendrys Gómez, C Josh Breaux, $11.75 million (to offset Donaldson's $21.75 million salary)

Peraza, 22, checked in No. 56 on our final Top 100 prospect list of the 2022 season. He hit .306/.404/.429 with three doubles and one home run in 57 plate appearances after making his MLB debut on Sept. 2, and he checks all the boxes to be an everyday middle infielder in the big leagues. It's a steep price to pay, but one the Yankees should seriously consider.

Plugging in either Rodón or López alongside Gerrit Cole, Nestor Cortes, Luis Severino and a healthy Frankie Montas would give the Yankees one of the deepest starting rotations in baseball, with Domingo Germán as terrific depth in a swingman role.

That's not all that remains on the shopping list, though.


2. The Yankees Also Need an Outfielder

Andrew Benintendi
AP Photo/Scott Audette

Pencil in Judge as the everyday right fielder and deadline pickup/postseason hero Harrison Bader as the starting center fielder, but the other spot in the Yankees outfield is still up for grabs.

Oft-injured veteran Aaron Hicks has hit .211 with an 83 OPS+ and 1.3 WAR in 162 games over the past two seasons, and while he's still owed $30.4 million over the next three years, counting on him to hold down an everyday spot is a recipe for disaster.

Rookie Oswaldo Cabrera saw some action in left field, even starting five games there during the playoffs, but he's probably more valuable in a super-utility role than he is tethered to an everyday spot in the outfield.

So who's left in free agency?

Brandon Nimmo is likely going to command north of $100 million, and whoever gives him that contract will be paying in part for his ability to man center field. With Bader on the roster, the Yankees would be wise to let someone else pay that premium.

Andrew Benintendi is a logical target after the Yankees acquired him as a rental at the deadline, but his age (28) and near-career year offensively in 2022 (124 OPS+) could drive his asking price beyond a range the Yankees are interested in paying.

The most appealing option in terms of dollars and cents might be a one-year deal with bounce-back candidate Michael Conforto. He spent the 2022 season in free-agency limbo after receiving a qualifying offer and then undergoing shoulder surgery. He has 30-homer power, but there will likely be some rust after a year on the sidelines.

An outside-the-box target to monitor is Japanese outfielder Masataka Yoshida, who was posted by Orix Buffaloes on Tuesday, per ESPN's Jeff Passan, and has 29 days left to sign with an MLB team.

The 29-year-old hit .336/.449/.559 with 28 doubles, 21 home runs and almost twice as many walks (82) as strikeouts (42) in his seventh professional season in Japan.

Of course, there is also the trade market, where one name stands out above the rest.

Pittsburgh Pirates star Bryan Reynolds will be talked about as a trade chip until he either signs a long-term deal or is in fact traded.

The 27-year-old has three years of club control remaining, which means the Yankees would almost certainly have to part with Anthony Volpe and more to pry him loose, but his 8.9 WAR the past two seasons ranks sixth among all outfielders.

Other potential trade targets include Ramón Laureano (OAK), Victor Robles (WAS) or someone from the Arizona Diamondbacks' long list of controllable outfielders that includes Corbin Carroll, Alek Thomas, Jake McCarthy and Daulton Varsho.

Best guess: The Yankees sign Conforto to a one-year, $18 million deal to slightly exceed the $17.5 million contract the Chicago Cubs gave to fellow rebound candidate Cody Bellinger earlier this week. It's a low-risk, high-reward move that pairs well with the long-term commitment they just made to Judge.


Are They Really Only 2 Pieces Away?

Brian Cashman
Michael Reaves/Getty Images

The Yankees, like most teams, would benefit from adding a few more established relief arms, and a left-handed bench bat would also be nice considering Anthony Rizzo, Cabrera and Hicks are the only players on the projected roster who hit from the left side.

But all things considered, if they can cross top-tier starter and left fielder off their shopping list between now and Opening Day, they will have as complete a roster as any team in baseball heading into the 2023 season.

The winter meetings are winding to a close, but there's still a lot of offseason left.