The Yankees’ window is still open, but for how long?

(Keith Allison – CC BY-SA 4.0)

There’s pretty much never been a time in my life when the Yankees’ title window wasn’t open. I was born in 1990, so I have no memory of the pre-dynasty teams that didn’t fare so well. I suppose the 2013 through 2016 clubs weren’t World Series contenders either, but that’s neither here nor there. Currently, the Yankees have a fantastic core that’s come close in each of the past three seasons and can undoubtedly win it all in 2020. In spite of missed opportunities, the organization’s title window is still wide open. That said, it may not be open for as long as you think with the current core.

Frankly, the Yankees window should never close. The Steinbrenners invest heavily in the club year in and year out, though they’ve become beholden to winning with a budget. Do I wish they spent more to acquire the likes of Justin Verlander, Max Scherzer, Patrick Corbin, and others? Of course, but this is the route ownership has chosen and it doesn’t seem like they’ll waver. Look, it is possible to win with a payroll below the luxury tax threshold, as Hal has been adamant about. But doing so is about to get much more difficult.

The Baby Bombers we’ve come to love in recent years are about to get much more expensive, which means the front office will have less wiggle room for external improvements. There are a number of arbitration raises upcoming for 2020, including two big name first timers: Aaron Judge and Gary Sánchez. Thanks to MLB Trade Rumors typically accurate arbitration salary projections and Cot’s Contracts, we already have an idea of the incremental payroll for next season:

Arbitration20192020 Proj.Increase
James Paxton $        8.575  $      12.900  $   4.325
Aaron Judge $        0.684  $        6.400  $   5.716
Gary Sanchez $        0.670  $        5.600  $   4.930
Tommy Kahnle $        1.388  $        3.000  $   1.613
Gio Urshela $        0.547  $        2.200  $   1.653
Chad Green $        0.568  $        1.400  $   0.832
Greg Bird $        1.200  $        1.300  $   0.100
Jordan Montgomery $        0.597  $        1.200  $   0.603
Luis Cessa $        0.579  $        1.100  $   0.521
Jonathan Holder $        0.522  $        0.800  $   0.278
Tyler Lyons $        0.087  $        0.800  $   0.713
Total $      15.416  $      36.700  $ 21.284

You can also tack on another $11.5 million to the year-to-year increase because Masahiro Tanaka, Aaron Hicks, and Luis Severino all have raises from 2019 to 2020 in their multi-year contracts. Now, the Yankees do have a decent amount of money coming off the books. It’ll be either $39.3 million or $56.5 million depending on Aroldis Chapman’s opt out.

That was a long-winded way of saying the Yankees will have $6.5 or $23.7 million of freed up payroll entering this offseason, which isn’t much for a team seemingly unwilling to exceed the luxury tax (at least not by much – they went back above the limit this season). Especially when you consider that they’ll need to re-sign or replace free agents like Didi Gregorius, Brett Gardner, and Dellin Betances.

This isn’t just a one year issue for the club, either. Guys like Judge and Gary Sánchez will get even bigger raises in years to come. Arbitration for Gleyber Torres and Miguel Andújar will come after next season. Sure, they’ll shed the big deals of JA Happ and Jacoby Ellsbury, but they’re going to need to spend in order to keep this core in tact.

All of this means that the Yankees are nearing a major decision point. If ownership doesn’t wish to veer off route and raise payroll, then prepare yourselves for some unpopular decisions.

In the short-term, it could mean eschewing Gerrit Cole in free agency. Despite the star hurler being an obvious fit, Brian Cashman and co. will be stuck between a rock and a hard place. It’s the same reason why we’ve seen the team pursue cost-controlled starters via trade (i.e. Sonny Gray and James Paxton) instead of big fish in the free agent market. They know the core’s payday is coming and unless Hal opens up the purse strings, the front office will have a number of difficult choices to make. They can either land the big free agents now and lose a few pieces from the core later, or keep the core together while passing on big name players on the open market.

Even if the team plays free agency conservatively, they still may need to move on from certain core players. Right now, it may sound inconceivable for the Yankees to let someone like Aaron Judge leave. But remember, they’ve already done this once before with Robinson Canó. Who’s to say they wouldn’t do the same with someone like Judge? Seems hard to believe right now, but I thought Robbie would be a lifetime Yankee. I mean, look at what the Red Sox are considering with Mookie Betts right now. It shouldn’t happen, but this is where the Yankees, Red Sox, and the rest of the league seem to be going.

At the same time, Brian Cashman’s actions have already indicated that the team is trying to prepare for the young stars coming of age. He signed Severino and Hicks to team-friendly extensions, and he assuredly will try to do that again over the next few months.

So without more investment from ownership, the length of this core’s title window could be shorter than you may expect. Given the club’s behavior in free agency in recent years, there’s a very real chance that significant improvements aren’t made in the short-term (i.e. Gerrit Cole). And in the long-term, the Yankees could break up its core in the name of winning efficiently. Neither sound great, but we should brace ourselves just in case.


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  1. brian

    Nobody wants Judge to be allowed to go, but I guess, the way the front office is thinking about it, Judge will get very expensive very soon, and is already 27. So giving him a long contract means you’re locking in a guy who may not age all that well as our favorite Large Adult Son. I’m not saying its the right thing, but guessing at their thought process a little. Gleyber is much younger and will get expensive as well, but you’d ostensibly be buying out his peak years with that large contract.

  2. RetroRob

    If the mid-90s to early-aught dynasty was playing today they’d never be able to keep them together. They are going to have to make some hard choices. The consistent contending championship teams have to forecast budgets not just for this year, but subsequent years, and make choices on players they want to keep and players they want to leave or trade. That may cost them Didi and Gardner this off season, two players who can contribute, but two players who can be replaced by either cheaper talent, or talent already on the roster. In this case, DJ and Tauchman. I suspect the Yankees are hoping that Chapman also triggers his opt out.

  3. Wire Fan

    Minor nitpick – you can’t purely look at salary increases to determine AAV changes. It works for players in arbitration, but a guy like Tanaka has one AAV regardless of year to year changes in salary. Assuming the Yankees are driven by the LT #, Tanaka’s salary bump next year is irrelevant.

    Didi + Chapman’s (if he opts out) combined AAV goes a long way to paying for Cole. Discount Happ’s contract heavily as he would no longer be needed (eat 7-10M?) and the LT space is a non-issue. There is also Dellin’s AAV too if they move on from him. Longer term the Yankees have over 60M coming off from Ells, Tanaka, Paxton and Happ…. There is plenty of LT space, this is purely a question of risk and having a big FA contract on a pitcher. It was the same question with Corbin, despite the front office BS that it was about paying the young core.

    This of course requires the Yankees to not be a slave to the super bullpen model. But a pen of Britton, Green, Otto, Kahnle is a pretty decent core (especially if someone like Loaisiga or Tarpley emerges as a useful piece). Add a cheaper FA piece and you once again have a really deep pen.

    • RetroRob

      Correct. The number the Yankees look at is the luxury tax. They manage to it.

  4. Saul Goodman, Esq

    I remember the early 90s and 80s quite clearly. I laugh I at the “The Boss would be rolling in his grave” types who think it’s all about buying every star out there. I watched the team not win a championship between 1978-1996 despite the owner outspending everyone. It’s criminal that Donnie Baseball didn’t see post season until his final year. Despite the disappointing ending of the past couple of seasons, I still think the Yankees are in a pretty good place and am confident they will add the necessary pieces to the core team to get them over the top.

    • DJ Lemeddardhieu

      I remember them quite clearly too and I don’t think there’s been a bigger drop off from father to son than George to Hal. Maybe Jack Buck to Joe Buck or Marcus Aurelius to Commodus. George had us in the World Series just about every year and there never was a player he wouldn’t go get. You need a young core to build around but you also need to supplement that core with True Yankees like Paulie, Tino, Coney, El Duque, Wellsy. Cashman has never understood this and had to be talked into signing DJ, who is the only guy that reminds me of that late 90’s team.

      Not getting Cliff Lee, Justin Verlander and Gerrit Cole cost us at least 3 WS and George would have had them all. The Astros remind me of the George Steinbrenner Yankees and this Yankees club remind me a lot of the Ted Thompson Packers. Never want to spend money and are always looking to not win now but 5 years down the road. This past offseason the Packers actually made some acquisitions and they’re on top of the league. What a novel concept.

    • RetroRob

      Agreed. I lived through the ’78-’96 championshipless dry spell.I watched George trade away excellent farm pieces who could have helped them win a championship. It was frustrating to watch. That is not the case here. This is an excellent team and an extremely well-run organization. There is no comparison.

  5. Roy

    I’m still amazed that of all the possible players, Cashman chose to extend Severino and Hicks. Both have very questionable track records, and it’s only a matter of time until their contracts are used as excuses not to spend.

  6. DJ Lemeddardhieu

    The window is open for the next decade plus plus plus, Derek. Gleyber, Judge, Sevy and Gary are the next Core 4 and as long as they’re young and vibrant we’ll be contenders. The original Core 4 went from ’96 – ’12 so this version will probably wear out around 2033 if this training staff hasn’t turned them into gluttons and cripples.

    If Chappy opts out let him walk. Not worth the money. His velocity will eventually start to dip and he won’t be as good. Britton can be the closer and you’ve got Green, Ottavino, Kahnle and Dellin as your set up men. Get rid of the concept of an opener and get more starters.

    If Didi doesn’t take the QO let him go. Gio can play 3B, DJ 2B, Gleyber SS, Voit 1B and Andujar can backup 3B and Wade super utility man. Re-sign Gardy to be the LFer. Make Stanton the DH to limit the wear and tear on his 80 year old body.

    The only guys on your list I’d give a paycut are Gary Sanchez so he has less money to buy food and Greg Bird who makes Stanton look like the Iron Horse. They don’t deserve raises. Not when the rest of us are scraping by on Dennys and the McDonalds dollar menu.

  7. mikenyc

    Its amazing Cashman has created this false-choice narrative that the Yanks can neither afford their talent down the road, nor sign every top free agent on the market…..alas, here we are.

    Locking down talent is only important when its elite talent, or if you are locking down certain areas of the roster to free up money to chase elite talent.

    I haven’t seen where Cahsman has done either vey well to this point…Severino’s jury s still out, and Hicks as well

    • RetroRob

      It’s not Cashman. It’s Hal. The money guy. Cashman has no ability to drive the payroll higher.

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