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Building Back Better – Part 2 (Evaluating the Players and a Trade Proposal)

by Cary Greene

October 25, 2021


The Yankees have a couple positional dilemmas to figure out this offseason:

Aaron Judge, assuming he isn’t made a free agent in the new CBA, needs to be extended. After the 2022 season, he will be a free agent. Some may want to trade Judge this winter, but that ship has sailed and the return he could have once fetched is now significantly less attractive. I believe extending him is the best solution.

Gary Sanchez will also be a free agent along with Judge after this year.

The Yankees need a shortstop to start the 2022 season.

Anthony Rizzo is a free agent and Luke Voit’s knees are a massive injury concern, more than likely ruling him out as a player who can be counted on.

Will the team attempt to sign or trade for a legitimate centerfielder?

What about the rotation, will the Yankees acquire more reliable starting pitching this offseason?


There are a lot of questions indeed, so let’s start by looking at positional issues and shortstop is a good place to start. Dropping a huge chunk of payroll on a long term deal for a shortstop seems a bit short sighted to me. I’d like to see a plan executed where the Yankees pass on expensive shortstops and figure out more of a short-term solution, while also keeping the lineup balanced. Fielding five right handed infielders, including the catcher, just isn’t going to cut it. I expect many of the top names to have pretty strong markets. Corey Seager will be a player for Yankee fans to follow as his market develops. Seager’s defense is in decline so he would be a stop gap option who would then shift to another position by 2023. It seems like he’ll draw a ton of interest though so I’m not optimistic that signing him to a big contract makes a lot of sense for the Yankees.

Trevor Story is another player who the Yankees clearly had some interest in at this year’s trade deadline. He’s younger and a better defender, but he’ll also probably have a pretty strong market and I’m not sure if Cashman and Steinbrenner will do what would be necessary to land him. Also, a few years from now, he’d be blocking Oswald Perazas and Anthony Volpe, so is it really wise to make a multi-year commitment to these bigger name shortstops that headline this year’s free agent class? I’m against giving a big contract to a shortstop because shortstop happens to be the one position that the Yankee farm system is loaded at. Why clog a roster spot and create Rule 5 Draft issues and make it harder to set a 40 man roster? Shortstop is the one position where the Yankees would be wise to remain flexible.

Making Trades:

Many will be interested in the Yankees trading various players who have fallen out of the active roster mix, such as Clint Frazier or Miguel Andujar, but I wanted to also illustrate which Yankee regulars, or once-regulars, have great trade value and which ones don’t, in the hopes we don’t have to read a lot of winter comments about how players who have lost their value should be traded for a superstar.

Doing this requires eyeballing the Yankee roster. I like to use, which is a good site to gauge a player’s current trade value. In fact, most trades that actually happen between teams fall very much in line with the values this site projects and its rare when a trade happens that is very far off from the site’s values.

I’ve used this site to determine where each Yankee mentioned is presently positioned, realizing that in order for a deal to happen, both sides need to have mutual needs satisfied.

The Most Tradeable Yankee Regulars:

Aaron Judge was this season’s most valuable Yankee statistically and the same was true of his actual trade value. Now that the season is over and he has, at best, one more year of team control, his trade value has slid quite a bit. Still, Judge is the most tradeable Yankee regular.

Surprisingly, Jonathan Loaisiga’s trade value has literally skyrocketed and we don’t need a website to really tell us that. He’s become a high leverage, extremely good reliever and he’s not a free agent until 2025.

Believe it or not, according to, Aaron Judge is only 6.5% more valuable than Loaisiga presently. That’s hard to believe but it’s a testament to the incredible season the fragile Loaisiga has had. These two players, Loaisiga and Judge, are the most tradable Yankee regulars.

Jordan Montgomery would slot in as the Yankee with the third highest trade value, as he is under team control for two more seasons. Loaisiga is 24% more valuable than Monty – to frame Monty’s value.

Close behind Monty is Joey Gallo, who would be the fourth most tradable Yankee regular, even though he has only one year of team control and during his time with the Yankees, showed serious concern about his inability to make contact. Gallo is currently 38% less valuable than Monty according to, which means Gallo is way less valuable now than he was at the trade deadline this year. Part of the decline is lack of performance and part of it is declining service time.

The Next Tier of Tradable Yankee Regulars:

Heading this group is Luis Severino who, despite his contract which is fairly reasonable, still registers solid value and there would be many teams interested in him as a one year roll the dice option. Severino is a free agent in 2023. Following Severino is in this tier of players is Domingo German, who’s value went up significantly this season. German isn’t a free agent until 2025 so he would be a player many pitching starved teams might want to inquire on. I’m not sure he factors into the plans for the Yankees next year so I expect Cashman to push hard to move German and capitalize on his present value.

Unfortunately, Gleyber Torres is the next Yankee regular in this group and his value is presently at an all time low. That said, he’s still easily tradable and I think it’s at least 50-50 that the Yankees move him. It doesn’t make a ton of sense to trade a once valuable player who might bounce back at the plate, but since Torres proved he’s no longer shortstop material and since the Yankees already have LeMahieu at second base, the team may consider just moving on from Torres. No doubt, Cashman will seek to get as much as he can for Torres if he does decide to move him, so Torres may be one of those players who winds up bringing back more than what the trade experts thought he might.

Closely following Torres in value is Nestor Cortes Jr, who’s value shot up significantly this season. In fact, if he has another good season, he may become as valuable as Luis Severino, or even more so. A large part of his value is that he’s not even Arbitration Eligible yet and when we couple that with the season he just had, suddenly he’s on the radar of many teams who are looking for pitching. I’m very against moving him by the way. He is my favorite current Yankee pitcher and I found myself really rooting for him this season. I’d be devastated if he were dealt.

The Less Desirable but Still Tradeable Players:

This tier of players is made up of players that the Yankees could easily trade in lesser deals this offseason, but they may want to hang onto many them because they all have value and provide vital services. This group is made up of Jameson Taillon, Chad Green Gio Urshela and Lucas Luetge. Any of these four players would be very easy to trade and they’d fetch a decent, but not spectacular, return.

The Highly Tradable Minor Leaguers:

The farm system’s most tradable assets in order are Anthony Volpe who is in a class by himself, followed by Oswald Peraza and Jasson Dominguez. Volpe is actually the teams single most valuable trade chip and he’s worth even more than Aaron Judge to put that in perspective. Peraza’s value remained fairly solid this season and Dominguez, once highly valuable, has taken a huge hit. has Dominguez as being roughly as valuable as Monty, just to help people understand what the Yankees could get in a trade, if they were so inclined to make one.

The Next Tier Easily Tradable Minor Leaguers

Luis Gil heads this list and he’s about as valuable as, say, Domingo German. He proved he’s oozing with talent this season but he also demonstrated legit concerns about his command. Alexander Vargas, Luis Medina and Austin Wells would make up the rest of this tier of attractive trade chips. Clarke Schmidt once was in this tier and I think he still is, but barely, as his value has steadily dropped due to lingering injury concerns and lack of innings pitched.

The Fringe Players who could be Included to Complete a Trade:

There are plenty of Yankees who could complete a trade package as a toss in, players like Mike King, Tyler Wade, Clay Holmes, Luke Voit, Kyle Higashioka, Estevan Florial, Greg Allen, Stephen Ridings..etc. It doesn’t make a ton of sense to trade most of these players, but they may absolutely be asked for as throw-ins in deals that feature other headliners.

The Players Almost No Team Would Give Much For:

Looking at a few Major League regulars and the Scranton-Shuttle type players who have minuscule to absolutely zero trade value we have a list of guys like Albert Abreu, Miguel Andujar, Socrates Brito, Nick Nelson, Tim Locastro, Chris Gittens, Gary Sanchez (yes, he has almost no value), Rougned Odor, and Clint Frazier, among a few others. Some of these players may be throw-ins, but more than likely the Yankees will have to prune through this group as they figure out what the 40 man roster is going to look like.

The Extremely Hard to Trade Players:

Giancarlo Stanton obviously heads the class here. Based on his contract, the Yankees couldn’t trade him if they wanted to – which they probably would love to be able to do. Cashman has failed to get enough value out of Stanton by being too petrified to play him in the outfield, but we saw that he’s more than capable of playing outfield this season and we also saw him impact a few games with his glove. Stanton actually finished the season with a 3.1 WAR, largely because he finally played a bit in the outfield. Going forward, the plan ought to be to make him very close to a regular outfielder as there was an obvious uptick in his numbers once he played defense. I’m a big believer in playing a player in a position where he is most impactful and for Stanton, that position is right field.

Aaron Judge, a player capable of playing centerfield, could easily be moved to left field for home games and that would make a ton of sense if the Yankees wind up trading Joey Gallo.

The next hardest to trade Yankee is absolutely Aaron Hicks. The Yankees will either need to eat a big chunk, or all of his salary or include extremely good prospects. I highly doubt Cashman will be able to do either and therefore, I’d say it’s almost a lock that Hicks is the team’s fourth outfielder at some point next season. I do think the Yankees need a plan in centerfield and it is highly probable that part of this off season’s agenda centers around strengthening this key position. When we look at the players that division rivals have in centerfield, can we honestly project another year of Brett Gardner and think that a plan such as that will compare favorably to say, George Springer?

What about Gerrit Cole, where does he slot in and is he a tradable asset? The answer is no, Cole’s massive contract, coupled with his late season swoon that culminated in a Wild Card loss to the Red Sox, would make him very difficult to trade. Moving Cole would require the Yankees to include a player of Jasson Dominguez’s stature, which would motivate the team trading for him to absorb the full Cole contract. That would never happen of course, because the Yankees would opt to eat a portion of the contract if they wanted to trade Cole, so suffice it to say, a solid mid-tier prospect or two would certainly be included in any deals.

DJ LeMahieu, Zack Britton and Aroldis Chapman make up the rest of this group. LeMahieu’s performance didn’t live up to his contract, which is still substantial and therefore, he’s untradable. Britton is injured and overpaid and Chapman is no longer reliable and also overpaid. This group of players will most likely be pimples on the books for this coming season, unless Cashman gets very creative.

The Players Who Are More Valuable if Kept in Pinstripes:

I also think there are a few Yankees who are way more valuable to the Yankees than they would be in a trade. Nestor Cortes would headline this group and as I mentioned, I became a serious believer in him this season. He attacks the zone and pitches with a lot of deception.

Other players the Yankees may want to hold on to might be Steven Ridings, Andrew Velazquez, Clay Holmes and possibly Mike King. It feels like each one of these players is absolutely worth hanging on to.


My First Trade Proposal of the Off Season:

Now that we’ve fairly assessed how well the Yankees are positioned, let the offseason begin. Which players would you like the Yankees to trade for this offseason?

Not to disappoint our readers, I’ll propose my first trade of the 2022 offseason. I think the Yankees are going to need to get extremely thrifty this offseason, so with that in mind, I’m willing to make a deal.

My plan would be to help the 2022 Yankees while also playing for the future so my first move of the offseason would be to fix the catching for at least the 2022 season. I also tip my hand that I’m going with Luke Voit at First Base to start the season, but I’d like a first rate prospect in the mix by the All-Star break.

Sit back, this is a blockbuster!

Proposed Trade with Kansas City Royals

Yankees Get:

Nick Pratto, 23 yr LH-1B – Triple A,

Andrew Benintendi, 27 yr, LH-OF – MLB,

Alec Marsh, 23 yr RH-SP – Double A,

Carlos Santana 35 yr 1B SWITCH HITTER – MLB,

Salvador Perez, 32 yr, RH-C – MLB

Royals Get:

Oswald Peraza, 21 yr RH-SS – Double A,

Gary Sanchez 28yr RH – C – MLB,

Albert Abreu, 26 yr RH-RP – MLB

Some notes:

I need insurance in case Voit goes down so I’m going to absorb Santana’s contract and use my financial might to give the team a backup plan for what seems like the next, significant, inevitable injury to Voit.

I’m also replacing Gardy’s utility spot with Benintendi, who is a more impactful player in every regard. I’d extend Benintendi for 4 years also, with a club option for a fifth.

Throwing in Gary Sanchez negates the need to pay him arbitration which saves some money which can go towards paying Santana’s bad contract. The Royals get the shortstop prospect they so badly need. They also get a starting catcher and an intriguing pitcher with a lively arm who showed nice flashes, finally, this season. Sanchez and Abreu are throw-ins in this deal. Neither has any real trade value. I’m simply clearing roster spots. The Royals would need to include Marsh in this deal to make it somewhat fair for the Yankees.

I would do this deal as a one stop – one fell swoop answer to many of the problems that Cashman has not been able to overcome:

We fix first base for next season and we have a future plan with Pratto – CHECK!

We finally replace Gardy and get younger in the outfield. Left handed hitting also improves a tick – CHECK!

We put a pitching prospect in the cupboard – CHECK!

We fix the catching and extend Perez for 4 years – CHECK!


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