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  • Writer's pictureAndy Singer

Andy Singer's Off-Season Plan

By Andy Singer

December 5th, 2023

While I spend most of my time evaluating rumors, the ideas of others, or roster decisions that the Yankees actually make, I have spent a lot of time thinking about how the Yankees should plan to get the roster back in shape this off-season. To be frank, the window in which to win with both of the Yankees' best players at something close to their peak, Aaron Judge and Gerrit Cole, is rapidly closing. As much as my proclivity is to hug prospects, this is not the off-season to hug guys outside of the very top of the Yankee farm system. I think the Yankees need to be much more aggressive than they have been in a long time in order to make this off-season successful.

I propose a series of trades and a signing or two this off-season. Obviously, it takes two to tango, and in one or two cases, I have no idea if the team in question would be willing to deal, which is all the more reason why the pot has to be sweet. Many of these proposed deals serve as frameworks for the types of deals I feel the Yankees should explore this off-season in order to build a winner, even if these specific deals don't happen. There are hard moves, including one that really made me second-guess myself, but the Yankees have put themselves in a position in which tough decisions must be made.

Let's get into it!


The top luxury tax tier stands at $297 million. I tried very hard to convince Hal Steinbrenner to show some willingness to go above this arbitrary budgetary constraint, but he wouldn't budge, as he has historically set a hard limit at the top tier of luxury tax. This is the budget I'm working with. For transparency, I used the current salary projections and estimates at Fangraphs to budget, which includes estimates for health insurance and ancillary costs, which are factored into the luxury tax calculation. I will reveal the Yankees' final budget at the end of the article.

Trade 1: Yankees trade Clarke Schmidt, Everson Pereira, Spencer Jones, and Will Warren to the Padres for Juan Soto and Trent Grisham

Let's get the elephant in the room out of the way to start. The Yankees and Padres have been hard at work discussing a deal, and I still believe the framework that I discussed weeks ago is in play. The Padres are getting a bit ridiculous by asking for 7 or 8 prospects, and they want good pitching. The Padres are in desperate need of pitching this off-season, but they also need to build a sustainable future, as the rumors of financial distress continue.

The Yankees get 1 year of possibly the best left-handed bat in baseball and an excellent defensive CF who hits from the left side and will help the Yankees get more athletic (and who has some upside with the bat upon closer inspection).

The Padres get two rotation pieces for this season, both of whom project to be solid average pitchers over the next couple of seasons; the Yankees' best upper-level hitting prospect not named Jasson Dominguez; and Everson Pereira, who has sat in the middle-back of most Top 100 Prospect lists since last season. Baseball Trade Values' Trade Simulator tool tells me this is a vast overpay, but I think this framework is closer to reality than the values listed for Soto in the simulator.

Free Agent Signing: Yankees sign Yoshinobu Yamamoto to a 7-year, $215 million contract with an opt-out after 3 seasons

There isn't much explanation needed here; Yamamoto is one of the best pitchers to hit the free agent market in years. Having watched as much video as I can possibly consume, I think Yamamoto is the real deal. The Yankees have to do what they can to sign him.

I'm not sure how high the bidding will go, but I think this bid should come close to reflecting current market conditions. Yamamoto gives the Yankees another high-octane starter at the front of the rotation, taking some pressure off of the guys returning from injury, like Rodon and Nestor Cortes Jr.

Trade 2: The Yankees trade Mike King and Kyle Higashioka to the Reds for TJ Friedl and Lucas Sims

This one probably comes out of left field for most of you. The Reds are a team that appears to be on the precipice of contention, but they need rotation help to stay relevant in a division that will likely get tougher this off-season. They are a team that typically doesn't spend much, so the trade market is the only way they can compete. Mike King appears to be an excellent starting pitcher, and I think teams will be willing to part with talent to acquire his services. The Reds make sense as a suitor. Their catching situation is also terrible, so while Higgy Pop is getting older and more expensive, he makes a lot of sense for a team like the Reds that need some stability.

TJ Friedl will remind a lot of Yankee fans of Brett Gardner. Friedl can run, defend, and makes a good bit of contact, with just enough pop to occasionally use the short porch effectively. The Reds have some offense, and Friedl is coming off of what will likely be his best season, so it makes sense to sell high. He'll still be useful to the Yankees.

Lucas Sims has strikeout stuff and inconsistent results out of the bullpen. He was solid last year, but his peripherals aren't quite as impressive. The Yankees have had success in the past with relievers like this, so Sims is a good target, considering his stuff.

Again, Baseball Trade Values tells me this is a slight overpay, which probably means I'm in the ballpark.

Trade 3: Yankees trade Gleyber Torres to the Marlins for Edward Cabrera

I said it would hurt somewhere. Given the Yankees' budgetary constraints, there is no room to keep Gleyber Torres and add significantly to the roster. A trade with the Marlins, who have long liked Gleyber, makes a lot of sense. Cabrera is a starter with tantalizing stuff, but one who hasn't quite been able to make the transition to mid-top of the rotation consistency. That said, the Yankees would ask him to pitch at the back of the rotation, where you can live with some inconsistency and hope for more.

I think Baseball Trade Values underrates Gleyber's value, but I went with it for this exercise. This is a fair value trade.

The New Lineup



LF Soto (L)

RF Judge (R)

1B Rizzo (L)

DH Stanton (R)

CF Friedl (L)

SS Volpe (R)

C Wells/Trevino (L/R)

2B Peraza (R)


C Trevino/Wells

OF Grisham

UTIL Cabrera

-Defensive Specialist infielder to be named later


Gerrit Cole

Yoshi Yammamoto

Carlos Rodon

Nestor Cortes Jr.

Edward Cabrera


Clay Holmes

Jonathan Loaisiga

Lucas Sims

Tommy Kahnle

Ian Hamilton

Scott Effross

Jhony Brito/Randy Vasquez

Matt Krook (L)

Final Budget: $296 million

I think this is a balanced roster that can contend for a championship. I am curious to see how all of you feel about it!


Robert Malchman
Robert Malchman
Dec 05, 2023

I would do these deals except for the King one. Why is one year of Lucas Sims any kind of upgrade over Michael King? King is going to be a mid-rotation starter at worst -- and even if you kept him in the bullpen, he's better than Sims. Friedl's good, lefty-hitting and under control through 2028, but if the Yankees get Soto, I don't think you need a placeholder for Dominguez.

Robert Malchman
Robert Malchman
Dec 06, 2023
Replying to

If you trade King, you guarantee he won't make any starts! Virtually all pitchers have an injury history nowadays. So you hoard effective starters knowing that some of them will go down with injuries.


Dec 05, 2023

I believe Torres might be included in a deal for pitching especially if Yankees get outbid for Yamamoto which is a distinct possibility ( I believe he signs with SF and have been putting this out there for weeks) if Ohtani signs with SF then I will be proven wrong because they won't sign both. It sounds like the Yankees have their best offer on table for Soto and Blue Jays will have to better their offer otherwise the Yankees get Soto for the rental year. Consolidation prize would be Roberts from Sox which long term would be a nice addition because Soto would be available next year for only a contract. As you point out, the wild card is…


Alan B.
Alan B.
Dec 05, 2023

Your Padres deal is fagetaboutit! First, only 2 pitchers and not one of King/Thorpe/Hampton. Second, Cashman doesn't putt money on the bench and you are parking Grisham and his salary right there. The only upside is for Cashman's ego, where Cashman replaces Florial with Grisham. I think when it's all done if the Padres trade Soto anywhere but to the Yankees, they won't get a deal close to what even the Yankees C package is. My take: They seem to want King, OK. But then the other pitchers are Brito & Warren. Or Warren, Beeter, & Vasquez. You take Schmidt, I'll put in Hampton, Warren, & Vasquez. Oh and of course Pereira in the deal, but Grisham ain't co…

Andy Singer
Andy Singer
Dec 05, 2023
Replying to

I know what the Padres are supposedly asking for right now; very few teams would actually give them 3 near-MLB ready pitchers, so I don't see it as likely. For Soto, I'd be willing to upgrade the second pitcher, but then I'd pull Jones out of the deal. The Padres need quality and quantity around the field, not just on the mound.

As far as Florial is concerned, I think we know that we agree to disagree. Grisham and Florial are not equals. I want a championship and I'm okay with slightly overspending to get good depth.


Paul Semendinger
Paul Semendinger
Dec 05, 2023


My plan (in short form)...

  1. Convince Hal that the Yankees' big advantage is that they can exceed the threshold

  2. Explain that even if the Yankees spend a gazillion dollars, they'll make a gazillion more.

  3. As such, get Soto. If the Yankees can keep King in the deal, great, if not, oh well. It seems they can get Soto without giving up the biggest hitting prospects.

  4. If they get Grisham in the trade, that solves CF, but, in case it doesn't...

  5. If not, they can trade for a CF - can the likes of Spencer Jones, Everson Pierera, Oswald Peraza be the centerpieces of a trade for Bryan Reyonolds or Luis Robert, Jr.?

  6. If not, I'm all-in on…

Paul Semendinger
Paul Semendinger
Dec 06, 2023
Replying to

Great idea.


Dec 05, 2023

your terms for a Soto deal seem reasonable and considerate of the needs of the Padres.

the trade with the Reds appears to be solid and Friedl might serve to hold down the center

but, while Torres is maddening and too often a real pain in the patoot, but you should try a little bit harder to convince Hal that dumping him for a back-end starter just to shave a few bucks from the payroll is, ultimately, bad business.

I think that it's a good idea to make room for Peraza, but also think that the team should hang on a little bit longer to determine whether DJ is gonna hold up and provide the offense that the team needs…

Dec 06, 2023
Replying to

true. it'll really cut into the profit margin

unless, of course, the Yankees gain a good deal of additional revenue from playing extra games and gaining additional fans and selling additional merchandise.

winning is profitable

I won't delve into exploring the supposition that Hal will gain a great deal of enjoyment from overseeing a winning team and putting to rest the claim that he's timid and tight with a buck.

sons like to surpass the achievements of their fathers (I've read that somewhere but would hesitate to ascribe to such supposition).

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