The Tuesday Discussion

December 2, 2025

***

This week we asked our writers to share a realistic, but blockbuster Yankees trade that you wish would happen at the Winter Meetings.

Here are their replies:

***

Ethan Semendinger -

The free agent market is BLEAK this year, which means the trade market is where deals are going to be made in spades during the Winter Meetings. Here are three names that I think are somewhat realistic players to acquire:

Player #1: Ketel Marte

Ketel Marte would be a fantastic addition to this team by providing the Yankees something they haven't had in a long time: a true good, proven, lead-off hitter. I'd start an offer for him with Anthony Volpe. (The Yankees can figure out shortstop with somebody else.) I'm over Volpe and his "local kid" story. He has had flashes of high-quality play, but New York is too big and bright for him. Between Marte and Chisholm, one could take over second base and the other gets center field when Grisham inevitably fails to live up to his 2025 performance.

Player #2: Steven Kwan

The Yankees are ultimately going to bring back Cody Bellinger on an overpayment of a deal. However, I would opt for a smarter deal by bringing in an even better lead-off option than Marte by going with Steven Kwan. They need a true left fielder. Jasson Dominguez has not been that guy. Start the offer with Dominguez and bring in the proven talent. 

Player #3: Joe Ryan

The Yankees are great at having talent maximize their entrance into the league. Luis Gil won the Rookie of the Year in 2024. He's also a question mark for 2026, as are many other starting pitchers. With questions surrounding Cole, Rodon, Schmidt, and Gil, it makes sense to get a reliable starter. Joe Ryan is that guy. Start the package with Gil.

Players Traded: Anthony Volpe, Jasson Dominguez, Luis Gil (among many prospects)

Players Received: Ketel Marte, Steven Kwan, Joe Ryan

Then, it's up to the Yankees to find a new shortstop...I wonder if anybody else has an idea for there?

***

Ed Botti - Corey Seager + Cash ($35mm) for Chisolm, Warren, Hess & Lalane. If they want to expand to include DeGrom, I’d be open to that discussion and consider Wells + in that deal.

 ***

Cary Greene - Many dominoes must fall this offseason for Brian Cashman to be able to identify the right players to either sign on the open market or for him to decide who to trade for. This week's question is asking us to be realistic, but to also identify a trade that would qualify as a block buster. Since the Yankees haven't made a major free agent acquisition yet this offseason, this question is especially challenging because I've been maintaining that if the Yankees do make a trade, they should do so only after landing the most impactful free agent they targeted. 

Positionally, I've coveted Corey Seager above all others, identifying him as most significant player the Yankees could trade for. However, there's a big problem with my desires here - the Rangers are reportedly not interested in trading him. Texas believers Seager is the face of the franchise and even though they're trying to reduce their payroll, the Rangers want to find other creative ways to accomplish doing that. In attempt to be realistic, I'm going to suggest Cashman make a very hard to turn down proposal to the Rangers for Seager. If they chose to pass, I have a backup plan and I will promise to stop beating the drum for Cashman to trade for Seager. 

My package below is an overpay, but it allows the Rangers to dump Seager's contract, insert a badly needed, ready now starter into their rotation, add a potential closer, stockpile a can't miss rotation piece and also, potentially replace the non-tendered Aroldis Garcia in the OF. They would have to at least strongly consider this overpay. 

Yankees Hard to Turn Down Package:

Rangers Get: SP Will Warren (or Cam Schlittler), OF Jasson Dominguez, RP Camilo Doval, MiB SP Bryce Cunningham

Yankees Get: SS Corey Seager

In my backup plan, the Yankees sign one of the available free agent pitchers currently on the market, while going hard after the Brewer's Freddy Peralta. It's a simple plan based on addition through subtraction. If the Brewers didn't like Will Warren, the Yankees could also offer Cam Schlitter in the below package. This trade makes the front end of the Yankees rotation way better while also solidifying the back end of the bullpen. 

My package is absolutely an overpay (again, trying to be realistic here), but that's what the Brewers will want for arguably the third best starter in MLB right now. 

Backup Plan:

Brewers Get: SP Will Warren (or Cam Schlittler), OF Jasson Dominguez, MiB SP Elmer Rodriguez-Cruz

Yankees Get: SP Freddy Peralta and CL Trevor Megill

***

Tim Kabel - If the Yankees are unable to sign Bo Bichette, I would like to see them trade with the Texas Rangers for Corey Seager.  The Yankees could send Austin Wells, Anthony Volpe, and Will Warren to the Rangers. If that was not enough, they could also send a mid-level prospect, most likely a pitching prospect. However, it would not be one of the higher end people such as Elmer Rodrigue- Cruz, or Carlos Lagrange. 

***

Paul Semendinger - if it is true that the Tigers are willing to trade Tarik Skubal, I'd say to Detroit, "Take any five players you wish not named Ben Rice, Aaron Judge, or Max Fried."

I believe Ethan will mention that Steven Kwan is a great target. I commented on that in an article about a month ago. Yes to Kwan.

***

Andy Singer - With a relatively weak free agent market, I think there are a lot of interesting trades out there. I was tempted to say Steven Kwan, but the more I dig into his profile, the more concern I have that we've already seen his peak; in fact, I'd venture to say that I prefer him hitting in the bottohttp://pitching.Herem of an order than the top, which is what the Yankees need. Kwan is fantastic defensively in LF, but his speed and baserunning are declining rapidly, and Yankee Stadium is among the worst in baseball for pure singles hitters like Kwan. I love him, and would be happy to have him, but if he's the "big" acquisition, he's fool's gold.

I am going in a slightly different direction, and this player appears in an upcoming Off-Season Plan I've drafted: Brendan Donovan.

We've heard for multiple years that Donovan is a preferred trade target of Brian Cashman, and this is the year something might finally shake free. Chaim Bloom plans to do a partial tear down in St. Louis in order to rebuild, which is long overdue with a weak farm system to go along with a big league roster bereft of enough impact players and pitching to compete over a full season. I suspect that Bloom will place a high price tag on Donovan, but also recognize that he knows he needs to get as much as he can while he can for a player like Donovan.

Donovan can play LF or the infield for the Yankees well, and he'd fit beautifully hitting in front of Aaron Judge. The Cards need young, controllable talent, particularly pitching. Here's a middle-ground trade that I think might make sense for both sides:

NYY Trades:

OF Spencer Jones

SP Carlos Lagrange

SP Bryce Cunningham

STL Trades:

IF/OF Brendan Donovan

I'm probably light on STL's asking price, but this is probably what a fair middle ground looks like.

***

James Vlietstra - Ok so the goal here is to dream up a realistic blockbuster trade. In order to be realistic, it has to hurt, if the Yankees are truly serious about improving. Well, I have a few here. 

First, I would approach the Detroit Tigers about Tarik Skubal. He is a two time Cy Young Award winner. He’s a 29 year old LHP in his last year of arbitration. He earned slightly over $10M last season and is probably going to command around $20M this year. 

The Tigers’ motivation for trading him is basically only so that they don’t lose him for nothing at the end of the year. But with only one year of team control left, as well as a pricy salary, the haul is going to be more of quantity than quality. 

I have put together a package of five players in exchange for Skubal. Four of which are part of the Yankees top 30, and the fifth made 33 starts in his second big league season last year. 

Will Warren developed into a quality starter and still has five years of team control. Also going are MLB Pipeline number 9 LHP Henry LaLane, (16) OF Dillon Lewis, (19) Cade Smith, and (30) Harrison Cohen. 

The next call would be to the Pittsburgh Pirates. Paul Skenes is a 23 year old RHP. He won a Cy Young award and still has four years of team control left. 

He is going to require a return similar to what the Cowboys got for Hershel Walker that preceded their early 90s dynasty. An offer almost too good to pass up that fills several positions of need. 

This haul is actually a 6 for 1.  Similar with Detroit, they would be receiving a solid starter with a career record of 20-9, with 3 years of team control plugging right into the rotation. 

Luis Gil could be a star in his own right. Next is a solid catcher and former first round pick with four years of control left in Austin Wells. 

The four prospects include (1) George Lombard, who is a SS and is a top 20 overall prospect and centerpiece. (5) Bryce Cunningham and (13) Kyle Carr both had terrific seasons last year and could be joining Gil in the rotation by 2027, and (27) Eric Reyzelman is borderline MLB ready to be in the bullpen. All six players could be in the majors contributing within two years. 

The final trade is a true blockbuster 8 for 2 with the Kansas City Royals.  Bobby Witt Jr and Maikel Garcia are both 25 years old. 3B Garcia has four more years of control. SS Witt has five years under contract along with seven more option years. 

In exchange will be four from the Yankees starting lineup and four of their top 30 prospects. 

Anthony Volpe and Ryan McMahon (along with $10M) will slide into the left side of their infield. Along with them will be Jasson Dominguez and Clarke Schmidt. 

(2) Carlos LaGrange, (15) Brendan Jones, (24) Jace Avina, and (25) TJ Rumfield are the prospects in this deal. Lagrange is touching 103 mph and could become a top tier starter. 

A lot of people will probably say that these deals would totally destroy the farm system by trading away 12 of their top 30 prospects, however that’s the main purpose of the minor leagues is to help rebuild the major league team. 

I am a Yankees homer and minor league enthusiast. I would hate to see these guys go. I would love to see them continue to improve and win a championship with them, however these are some generational players that they are getting in return. 

Based on WAR, let’s see where we are versus our guys from last year:

Out:

McMahon 2.3

Schmidt 1.7

Volpe 1.6

Gil 1.0

Warren 0.6

Dominguez 0.5

In:

Skenes 7.7

Witt 7.1

Skubal 6.5

Garcia 5.8

These trades would be improving the Yankees biggest areas of need. Witt and Skubal AAV would be around Trent Grisham’s $22M. Garcia and Skenes combined will be around $8-10. Probably all four would cost $50M in 2026. 

The Yankees would need a catcher, which they are known for producing. For this year, sign JT Realmuto. 

By bringing in 27 more WAR into the team, they can put Spencer Jones in as the every day CF and live with his 30%+ k rate. 

And they would still have Schlittler, Rodriguez, Hess, Hampton, Dixby, selvidge, and Beck in their system.