Didi and Dellin: A Musing on the Future

August is here: the proverbial dog days of the baseball season and the time when I start counting down days until I’m back at work. I’ll understand if you don’t exactly sympathize with me on the latter. A byproduct of that is my teacher’s mindset of planning for the future has kicked in and it’s made me think about Didi Gregorius and Dellin Betances.

Both the star shortstop and injured reliever will be free agents at the end of the year. Before the start of the season, I (and maybe you) thought bringing them back would be a foregone conclusion. I’m sure I advocated for extensions for both of them before, during, and after the extensions the Yankees gave to Luis Severino and Aaron Hicks. Now, though, I’m having some doubts.

Dellin Betances, when healthy, is one of the best relievers in baseball. Given his relative longevity compared to most relievers, we could argue that he’s the best reliever in baseball when he’s healthy and at peak powers. The Yankees’ bullpen has been fine without him.

Didi Gregorius is a great defensive shortstop and has flourished offensively with the Yankees. The Yankees, however, are flush with infield talent and could easily cover his loss as they did when he was out in the beginning of the year.

The other factor at play is that the Yankees have gotten quite choosy with how and on whom they spend their money in free agency. It’s easy to see how this will play out and what lines they’ll use if and when Didi and Dellin aren’t retained.

“We didn’t want to guarantee X years and Y dollars to players coming off injury.”

“We have a lot of great talent as it is. We’ll miss them, but we can make up for it.”

“We can get similar production for a better value with the guys we have.”

To an extent, all of these points are true and will be true in the offseason. The risk attached to both players is increased after injury, especially in Betances’ case. Free agency isn’t what it used to be and the Yankees could play to that trend. And given Gleyber Torres, DJ LeMahieu, Gio Urshela, and the will-be-returning Miguel Andujar, the Yankees’ infield situation looks pretty good, even without Didi. Despite all of those potential givens, I don’t buy any of them.

Let’s start with the cost. The Yankees can afford just about anything. They make enough money that they can eat a bad contract–years wise, money wise, whatever–and not have it affect their on field product too much. Money is also the biggest advantage the Yankees have over other teams. Considering all other avenues of talent acquisition are restricted, the Yankees need to flex their financial muscle in free agency.

There are times when this might go against their philosophies and their analytics guided evaluations, but given the context the team is in, they could stand to take some risks. This is a team with a wide open competition window, aided by young talent like Torres, Gary Sanchez, and Aaron Judge. Their costs are low, which should allow for the Yankees to splurge for free agents like didi and Dellin.

Counting on repeat performances this good from DJLM and Urshela might be a touch risky, especially in Urshela’s case. Andujar, as talented as he is, is a complete question mark at this point. Relievers, even ones as solid as what the Yankees have, are volatile, and given the Yankees’ spotty rotation situation, more bullpen depth might be needed. This is all to say that the best course of action is to stockpile as much talent as possible and let the chips fall where they may. As this year has shown, just about anything can happen and there’s no such thing as too much depth or too many contingency plans.

If I had to venture a guess, I’d say the Yankees will more likely re-sign Betances than Gregorius. Cynically, I think that’s because they could get him cheaper because his injury was more extensive this year than Didi’s was; there’s a chance Dellin doesn’t even throw a pitch this year. I’d also assume they think the bullpen is a bit less stable than the infield, which is true of just about any situation. But if I had my way, they’d both be back in pinstripes for 2020 and beyond.

I just enjoy rooting for Didi and Dellin. Dellin is a homegrown, local guy who worked real hard to get where he is and overcame a lot of baseball adversity to turn himself into an All Star reliever. Didi represents all that’s right with baseball. He’s enthusiastic. He’s charismatic. He’s charming. He’s multilingual. All that aside from the fact that he’s just a damn good player. If you can’t root for Didi, well, that’s on you.

The immediate future portends great success for the Yankees. They’ve got a big division lead and they look unbeatable at times. The longer term future, though, is, as always, uncertain. It may not contain Didi and/or Dellin but I hope it does. Hopefully, I’m not alone in that.


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  1. Mike

    Great analysis. I love how you go back and forth between head and heart. Baseball has become more and more data driven, but clubhouse chemistry is not quantifiable. Surely, much of the Yankee success this year in overcoming injuries is due to team chemistry. The Yanks are loaded at infield and reliever talent. They could excel without DiDi and Betances. But I’m with you on this one. My heart and head say bring them both back.

  2. mikefoxtrot

    DD plays excellent defense and hits well from the left side, and the team has few good lefty bats.

    they could move Gleyber to short, but he doesn’t have as much range as DD.

    unless they are gonna replace Gregorius with Lindor, they should re-sign DD

  3. Wire Fan

    SS’s age 32 and older who qualified for the batting title over the last 5 years

    2015: Jimmy Rollins, Jhonny Pheralta, Alexei Ramirez, Jose Reyes
    2016: Alexei Ramirez
    2017 Reyes (though he played a bunch of 2nd and 3rd)
    2018: none
    2019: Brandon Crawford

    Age 32 would be the third year of a potential Didi deal. Only 2 of the 7 seasons above were over 1 WAR, and the highest was 2.1 fWAR.

    I’d go max 3 years on a deal (or team option 4th year?) as that third year is potentially ugly. And will Didi’s bat play at 2nd or 3rd at that age? if his bat speed goes, the offense will likely crash hard as he has no patience at the plate.

    Also not sure how much demand there will be for Didi as most contenders with money to spend have a SS. Who might be shopping for one this winter? Brewers? White Sox (if they think they are at the end of their rebuild)? Texas (if Andrus opts out)?

  4. RetroRob

    Price is key here the way teams manage to the salary cap, err, competitive balance tax. It’s not just next year’s payroll, it’s factoring in 2021, 2022, and having enough headroom to sign Judge, Sanchez, etc. while maintaining a top team and enough payroll flexibility to bring in the right talent each year. The Yankees don’t have to resign either player, so they may simply let both hit the open market and then let market prices dictate. Good price, bring them back; high price, let ’em walk.

    How many teams, for example, are in the right position to pay for a starting SS of Didi’s caliber and salary? A contending team likely already has a good SS. The position is deep currently. A non-contending team won’t want to direct their money to a SS about to turn 30 knowing they’re a few years away. Despite his talent, Didi’s market may be limited to just a few teams. If the Yankees see that, they may let him file for free agency and then see if they can get a bargain. Fans are emotional. They like Didi, they believe he’s a must have. The Yankees won’t be emotional here. If someone blows Didi away with an offer, they probably let him walk, knowing that Gleyber slides right over to SS, DJ takes over at 2B, they have both Andjuar and Gio to cover 3B, with the versatile Estrada to back up across the infield.

    Dellin? If he returns in September and is pitching high-leverage innings in October, he will find a wider market than Didi. Everyone wants a top relief arm. He simply needs to show he’s healthy in the coming weeks.

    The Yankees may (and should) want to make a big play for Cole. To do so, they’ll need to find money elsewhere. One way is to let Didi and Dellin leave, and hope that Chapman decides to opt-out. I’m sure they’re fine with Chapman returning. He’s still quite good. They also may prefer to direct his money elsewhere. If Chapman really wants to remain with the Yankees, he best be careful.

  5. CountryClub

    My guess is they sign one of the two. I’m a bit concerned about Betances moving forward. I’d be a bit worried that this year is a trendsetter. With Didi, no more than 4 years. Anyway, it’ll be interesting.

  6. madrugador

    I’d bet they resign Didi. Yes, they’d be buying some decline years but I think the two sides work out a deal that is neither as lucrative as Didi wants nor as cheap as Hal wants to be. Dellin is another matter. He’ll be 32 next year and will still have that shoulder spur. I don’t see him as a power pitcher aging well. I think they will either sign him to a one year deal so he can prove himself or he’ll walk.

  7. Yanks are better with Didi. As a person, he’s everything you could wish for.

    The only negatives I can’t get comfortable with is his obp and the fact that he’s pushing 30.

    I could see the Yanks offering him 3-4 years at $13 mil or so and extending him the QO if he turns it down.

    The way all the front offices are valuing free agents, I’d be surprised if Didi gets significantly more than $50 mil from anyone.

    I’d give 60/40 odds Didi stays a Yank next year.

    Payroll is already tight for next year, Tank, Ells don’t come off the payroll til 2021.

    • RetroRob

      I was going to throw this point in on my note above, but it was already getting long. I outlined why the Yankees may let Didi leave, but one aspect he has going for him is he’s a lefty bat. The Yankees no longer are obsessed with having lefty hitters in their lineup, but they clearly want some.

    • mikefoxtrot

      inreality, the payroll is far from “tight”.
      the team would turn a profit even if the players cost $300M.

      the real question is whether the Yankees decide to sign, at great cost, a frontline starter such as Gerrit Cole and try to squeeze Didi.

      of course, the team could decide to extend a qualifying offer and hold Didi for one year

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