Why Didi Gregorius might not fit the Yankees’ offseason plans

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Gerrit Cole or Didi Gregorius: Which would you rather have on the Yankees next season?

That shouldn’t be an either/or situation; The Yankees can afford both. However, it’s not hard to envision the Bombers choosing to upgrade pitching this winter at the expense of their shortstop of the last half-decade.

Gregorius has been an integral part of the Yankees’ turnaround. He stabilized shortstop after Derek Jeter retired. He turned into a power-hitting machine from the left side. Perhaps most important, he’s helped make the Bronx Bombers fun. You don’t put a price tag on that last part, yet one can’t help but mention it.

But he may not get to see the Yankees’ current run through to the end, to no fault of his own.

Gregorius, after all, is a free agent after the season. He’ll be 30-years-old on Opening Day 2020 and is making $11.75 million this season with a raise presumably coming on a multi-year contract.

Though next year’s free-agent market has a handful of quality third basemen, headlined by Anthony Rendon, Gregorius should be the top shortstop. As of now, the only other top shortstop set to hit free agency in the next two years is Andrelton Simmons. Gregorius has the all-around skills and personality to thrive anywhere.

It’s reasonable for Gregorius to expect much more compensation than the top corner infielders on last year’s market — Eduardo Escobar and DJ LeMahieu, each of whom received less than $25 million on their contract. Free agency is broken and unpredictable, but even with a qualifying offer, he should command 3+ years at north of $13 million annually. Perhaps much more than that, though who knows with the current climate for free agents?

This wouldn’t be a problem except the Yankees play with a budget. A self-imposed one, and one that allows plenty of room for profit, but a budget nonetheless. When thinking about the Yankees’ free-agent plans, you have to keep in mind the top luxury tax tier, which will be $248 million in 2020.

The Yankees have something around $230 million on the payroll this season with CC Sabathia, Brett Gardner, Dellin Betances, Austin Romine and Gregorius coming off the books after the season. That accounts for around $36.3 million. Aroldis Chapman could opt out, but the Yankees would then have another hole in the bullpen.

At first glance, it’s easy enough for the Yankees to re-sign or replace all of those players and stay under the tax. They have a ready-made replacement for Gardner in the organization. However, as anyone who watched the last 10 days of Yankees pitching noticed, they could use another starter (or three), preferably high-quality ones.

Gerrit Cole and Hyun-Jin Ryu headline a robust starting pitcher market (compared to last season) with Madison Bumgarner, Jake Odorizzi, Zack Wheeler, Cole Hamels and Rich Hill set to join them. Stephen Strasburg could be another high-profile starter out there if he opts out.

If the Yankees want to play in the Cole-Strasburg-Bumgarner free agent market, they’d begin to start bumping up against the competitive balance tax. Cole, who will be 29 next season, could command $200 million and over $30 million annually. Strasburg, 31, would take a similar per-season commitment. Even if the Bombers choose to go for lower-profile starters, they’ll still have to pay out a significant sum over Sabathia’s bargain deal.

Let’s say you get Cole for $25-30 million a season. That bumps the Yankees payroll to around $220 million, give or take. If they want to re-sign Betances or another reliever — far from a given if Chapman is retained — he would add another $9-10 million. This is before you lock in a backup catcher, fourth outfielder, extra starting pitcher or Gregorius, and leave room for call-ups and trade deadline upgrades. They’ll also need to hand out raises in arbitration to Aaron Judge and Gary Sanchez, which further adds to their payroll.

Dingers for Didi

So a big starting pitcher may limit the Yankees the room to sign Gregorius under the top luxury tax tier. That would be crushing to fans and perhaps to the team as well, though there is a successor waiting in-house: Gleyber Torres. The Yankees could shift Torres to short, allow LeMahieu to man second base and give third base to Gio Urshela, Miguel Andujar or a cheap, veteran alternative. (They could also eschew a pitching upgrade and sign Rendon, though that doesn’t make as much sense over keeping Gregorius).

This would be a short-term decision with LeMahieu becoming a free agent in the 2020-2021 offseason, but it’s a potential solution to the Yankees’ luxury tax questions in 2020. Torres can fill shortstop long-term, but he’s talented enough to play second base as well. Perhaps they view Thairo Estrada on next season’s roster.

Gregorius still fits the roster, contrasting with the Yankees’ glut of right-handed power bats. Furthermore, the Yankees’ infield depth this season served them well as injuries overtook other parts of their roster. Losing Didi’s bat, plus his clubhouse presence, would be a blow.

Of course, the Yankees could find other ways to shed salary. They could try and trade Jacoby Ellsbury’s $22.1 million contract for a larger overall deal that comes with a lower luxury tax cost. This is a method perfected by the Dodgers (see: Kemp, Matt) in recent seasons as they flirted with exceeding the luxury tax. They could also extend Aroldis Chapman at a lower AAV.

I don’t mean to sound alarm bells as this is both far too early and maybe not even something the Yankees consider. They know Didi is valuable and fits in New York. However, this isn’t completely bizarre and worth some light-hearted speculation in the interim.

The Yankees can both sign top free agent pitchers and retain Gregorius, or they can simply extend Didi and find cheaper alternatives on the pitching side. His presence has been invaluable to the Yankees, and keeping him should be one of their top priorities this fall. Still, with the team’s budget and questions around the roster, the front office could view him as expendable.


Aaron Boone Evaluation Survey: July 29th, 2019


The Yankees still need to put the Red Sox away


  1. RetroRob

    Sadly, even the high-revenue teams (Yankees, Dodgers, Red Sox, etc.) will knowingly hurt their chances by not improving where they obviously need improvement. Look no further than the Red Sox and how they’ve treated their bullpen this year. The Yankees are now in that territory too. That’s why I suggested recently that both Didi and Gardner won’t be back in 2020, as the Yankees will use the $20M in savings to direct toward a Gerrit Cole signing. That’s why they are seriously looking at Mike Tauchman this year. He’s the potential Brett Gardner replacement in 2020 and Gleyber slides over to SS to replace Didi, DJ takes over at 2B. Thairo becomes the all-purpose backup.

    It may not happen, but we can’t rule it out these days. MLB has a salary cap.

  2. dasit

    if didi is not in the yankees’ offseason plans then the yankees are not in my foreseeable future plans

    emotional overreaction? probably

  3. vincent gagliano

    Yeah, I can’t imagine not resigning Didi. Judge is going to make a huge jump is first year in arb, I truly don’t know what to pencil in for Sanchez. I’ll leave that to brighter and less busy minds than my own.

    I would welcome an opt out for Chapman. Not because I’m reacting to his recent struggles BUT 18mm p/yr is out of date with the market for relievers. I think that Britton, Dellin, Otto, Green, and Kahnle is fine considering Montgomery, potentially Garcia gets a first year like Sevy had in the pen.

    Getting Cole not only improves our rotation, it takes away from HOU. I think you could shave 5mm or so off the books from a team taking a chance with Happ. Cole, Sevy, Paxton, Tanaka German is pretty gnarly. Cole quite honestly may shatter every record for SP in free agency. In a year from next off season Ells is off the books, as is Paxton and Tanaka — maybe Garcia is a beast and can fill in a spot, maybe Montgomery, but there’s a lot of money off the books.

    Finally, it’s important to have a sound backup at catcher. I’m the biggest fan of Sanchez but a guy like him really needs a competent backup because he consistently gets hurt, he has defensive make up concerns, etc. We need not replace Romine but improve from him.

  4. Dididropsknowledge

    This decision will tell us whether or not Cashman is going to go in a different than the last dynasty. In the last dynasty, he signed most of the home grown players when they hit free agency. But the new Cashman:

    A. Values value and seems to be more cost conscious.
    B. Seems to pull above average players off the scrap heap at will.

    So the question is, will he do the old Cashman thing and try to keep the band together at all costs? Or will he unsentimentally trade/let players walk once they become expensive, confident that he can find low cost players to replace their production?

    The Didi decision will us give us a clue as to which direction Cashman and the Yankees are headed.

  5. Joy Illimited

    I sincerely hope they sign him while still committing to top-tier pitching. With ellsbury coming off the books in the following year, blowing the luxury tax for one year shouldn’t be that onerous for Hal’s wallet. Getting into the 240s would be not much higher, really, than the first half of this decade’s payroll.

  6. SM

    How did they give Happ a two year significant money deal knowing that they have a budget and Didi was an impending FA. That is some short-sighted “thinking.”

  7. Brian M

    Nope. Don’t wanna think about Didi on another team.

  8. george grossi

    Didi is a warrior. Look how quickly he came back from injury. He should stay

    • Andrew

      I think there’s a good solution to this. With all the contracts coming off the books this offseason we can create a little more room by trading J.A. Happ. I think (and I could be wrong) he will still have value this offseason as several teams wanted him last offseason and he will have only two years left. I could see several teams taking his salary on. If we were to sign Cole, we would have a rotation of Cole, Sevy, Masa, Paxton and German with Montgomery and Deivi waiting in the wings for depth. Signing Didi might make things tight with the luxury tax but like another poster said it would only be for one year until Ellsbury is (finally) gone. What do you guys think?

      • SM

        I don’t think Happ s tradable without including a prospect.

        • Wire Fan

          The main concern with re-signing Didi is the contract length. From 2016-2018 there was only one SS age 32 or older who qualified for a batting title. If he has to move off SS shortly into the deal, is it worth it? 2nd base FAs are generally far cheaper.

          The Yankees should spend on a starter if there is one they like. After next season Tanaka and Paxton are FAs, and maybe Happ (vesting option may not kick in). They also have Ellsbury’s money coming off the books, so if they pushed into the top tier it would probably only be a 1 year thing.

          This situation also shows the absurdity of the Corbin decision once again. For just 7M AAV more than Happ, re-signing Didi wouldn’t have been an issue and they wouldn’t have as much need for a big time pitcher this winter.

          • Wire Fan

            Sorry – not meant as a reply. Damn WordPress!

          • Enoch Charles

            As a Yankee fan,I truly believes that this is business. But unto myself don’t believe they will not sign didi…imagine wat he could do..what would you do if you where Cashman?remember the brosius sign?and barfield..sojo..Fernandez was going to be a free agent back in the 93 season with the Toronto at that time..Kansas city was after him…you guy’s forget that..?they sign him and make room for Derek Jeter…so I believe they will do what they must…and as for the winter…a few years ago Kansas city show us that you don’t need a highend pitcher to win it all..you need guts..you need commitment on the field of your players to do so..and they got it from the players…so signing him is a move the Yankees will do …not a big contract…because they still need pitching…

      • No way they let that third year trigger. It’s a 2 year deal for Happ. If you pay down some of the $, I think you can find a taker who will make sure that third year doesn’t trigger.

        • RetroRob

          Correct. They have full control over letting (or not letting) that option trigger.

          If Happ is pitching great, they’ll likely welcome him back. Mediocre or worse pitching? It will never vest.

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