Mailbag: Did the Yankees Miss their Championship Window?

Happy Tuesday, everyone. It’s a cold and dreary Tuesday several weeks into the lockout, and there really isn’t that much to talk about. I can’t really remember a time I’ve cared less about baseball than I do right now, and I think the same is true for many of us. Oh well. Not much we can do about i.

Anyway, it’s time for a mailbag – at least an abbreviated one. We got a bunch of questions this week but I wanted to spend more time on one question in particular, because I think it gets to the heart of so much Yankee fan anxiety these days. We’ll get to the others next week, and if you want to send your own question in, shoot us an email at To the question!

Daniel Asks: Do you think that the Yankees botched and squandered this potential championship window?

This is a simple question, but one that cuts bone deep for most Yankee fans these days.

After the unexpected joy and success of the 2017 season that ended a week too early, most fans, myself included, could close their eyes and see an emerging Yankee dynasty. It was hard not to! They core of the team looked to be ascendant superstars with a solid farm system to boot. Of course, the Yankees immediately traded for Giancarlo Stanton, hot off his historic 2017 campaign. It was the most exciting time to be a Yankee fan in a decade.

And while the Yankees won 100 games in back-to-back seasons following that trade, they didn’t win a title – and things have only gone downhill since. Here is an illustration by winning percentage:

  • 2017: .562 (lost to Astros in Game 7 of ALCS)
  • 2018: .617 (lost to Red Sox in Game 4 of ALDS)
  • 2019: .636 (lost to Astros in Game 6 of ALCS)
  • 2020: .570 (lost to Rays in Game 5 of ALDS)
  • 2021:.568 (lost to Red Sox in AL WC)

No matter how you slice that, it is disappointing. The Yankees appear to be trending backwards – nobody who watched the Yankees in 2020 or 2021 can deny the team was anything other than infuriating. With the sole exception of Aaron Judge, every key player from that 2017 core (and those who were going to augment it) has regressed. They’ve been humiliated in four straight postseasons at the hands of their biggest rivals. (I am exempting 2017 since that was not embarrassing.) And on and on. You know the drill.

But did they squander the window? The answer, unfortunately, is complicated.

First, let’s consider the obvious. Over that period, they added premier talent, including Giancarlo Stanton and Gerrit Cole. Last year at the deadline, they added Joey Gallo, who will certainly rebound in 2022. And they’ve made a number of smaller signings and trades that have bolstered the team significantly. They did this, and you can’t ignore it. It happened.

The tension is what they didn’t do. Even as they added Giancarlo Stanton, they shed $50 million in payroll before 2018, and they stayed under the luxury tax threshold in both 2019 and 2021. Over that period, they passed on other elite talent, including Bryce Harper, Manny Machado, Patrick Corbin, and Justin Verlander (in 2017). That also happened, and you can’t ignore that, either.

I think that they could and should have done more to bolster their team in every single one of those offseasons, and at each of the deadlines, excepting last year. That would have given them a better chance to win the World Series, even though they had a pretty good chance as it was. On the other hand, they’ve been right there. So it’s hard to say that they “blew” it.”

Finally, every team blows their championship window – until they don’t. The Dodgers were in much the same boat until 2020, and their fans were up in arms, too. Catastrophic playoff failures and perceived operational deficiencies cost them, too. But they they won, and that was that. The same can and very easily could happen to the Yankees. After all, this about says it all:

It makes me sick that the Yankees have the second-most wins, by a lot, in baseball since 2010 without winning a title. But they also have been winning a lot of games, and that’s not an accident. That necessarily keeps the window open. Keep getting in, and good things will happen eventually. That’s the idea, at least.

The best indicator of future success is past success, so I have no reason to believe the Yankees will shut their window any time soon. But it sure would be nice for them to ascend baseball’s Mount Everest again, wouldn’t it?


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  1. MikeD

    Sorry if this ends up as a repeat post. I hit send and the last one disappeared.

    Sadly, I’m going to answer the question in the headline as a Yes.

    As I responded to someone else in this thread, the current team is not like the 1980s version that needlessly traded away very talented young players, stupidly turned one of the best young left-handed starters in the game into a reliever, and failed to build out its starting pitchers (collusion may have played a part in this). Those teams were flawed. This group has been very good, but Hal has left them short in an area of their greatest strength, the card is father player well: money.

    When the Red Sox got bounced from the playoffs for a second straight year in 2017, it was clear what they needed in 2018. They went out and spent and brought in JD Martinez. They blew past the luxury tax threshold and brought home a championship. Hal, during the Yankees window, has twice pulled them back under, most painfully last year where they were giving away prospects and MLB players (Ottavino to a rival) simply to stay under an artificial threshold. It’s a team not fully committed to winning. What do they need the most? Uhh, a SS. The greatest free agency class in SS’s dropped right in their lap, and they’ve so far sat it out. It’s beyond amazing.

    The Dodgers comparison isn’t a clean one. They have legitimately built an NL dynasty over there, winning eight straight NL West titles (it took a 107-win Giants team to barely end that streak), and they’ve been the NL Champions three of four years. That’s not a coincidence. Yes, there is some luck in the postseason, but some teams are built better to win. The Dodgers have been that team. What did the Dodgers do after winning last season? They went out and paid $40M a season for Bauer. You can hate Bauer, but it shows the Dodgers weren’t content to sit back. Hal is content to sit back even with winning nothing. I can’t honestly say the Yankees have been better in the postseason than the Astros or Red Sox. Some times you do lose to an inferior team. Not the case here. The only team that looked like a champion was 2017. They’ve been out managed and out played by better managers and by better squads since 2017 because Hal has left them short by not utilizing the one resource he has, the one that we as fans have given him.

    The window is not quite closed yet on this squad. Go out and sign Correa. I don’t want to hear Yankee fans saying they don’t want him. I don’t care if Judge may have an issue with him. All indications are he’s respected by his teammates. Judge and Correa will likely get along well once they’re on the same team. The Yankees need some edge. They also need a SS who can field and hit. If not Correa, then Story. Either makes the Yankees better…by a lot.

  2. DanGer

    Also came to my attention that Roderick Arias (NY recent int’l signing) was born in 2004. That means NY has a single WS appearance in his lifetime…

    • MikeD

      Well, we’re depending on him to fix that! Seriously we are, although hopefully others do before he arrives : -)

  3. DanGer

    My feeling has been that this off-season will be the inflection point.

    Still possible they add some combo of Correa/ Olson/ Marte / Bassitt / etc and go hard for title.

    Or, they could say the $153M Braves beat the $271M Dodgers & $195M Astros on their way to a title so we need to “trust the process”, and hope to luck into a ring

    i don’t think we can say anything for certain right now.

  4. Broussard Yankee

    It is hard to argue that they have not and are not continuing to blow their window to win a WS. One could reasonably argue that in 2021 the Yankees were the fourth best team in the ALE, behind the Rays, Red Sox, and Blue Jays. With the absence of any obvious improvements to the team, there is no reason to see any significant change. They still do no have a legitimate SS or 1B. The CF will probably be on the IL by May. And they need SPs. And, they are relying on bounce back seasons from DJLM and Urshela, which may or may not happen.

  5. Chris_S

    Yankees also won the the most games in the 1980s. Whoopity damn do.

    • Scout

      Exactly. George S loved to brag about that. No one cared. if you get this close this often, you better go all in …or go home.

      • MikeD

        This is true, although even I in my annoyance recognize this is very different than the 1980s. They are well run, while George traded away a championship or three in the 1980s. The problem with Hal here is he is not closing the deal on what has been at times an excellent team. Now they’re trending backwards.

  6. Jack Helmuth

    I can handle not winning the World Series over this stretch of time. It’s hard to win it all in this sport! Injuries, bad luck, opponents cheating… all sorts of things can get in the way, and that’s ok.

    What I can’t handle is the complacency and not doing anything necessary (within the rules) to win! That’s where they’ve failed. Cutting payroll twice in an obvious championship window to get under an arbitrary luxury tax threshold? Obscene. Trading guys to cut payroll (Luis Cessa type deals)? Laughable. Having basically the same payroll last season as the 2005 Yankees? Negligent behavior.

    There’s no sense of ferociousness. No “eye of the tiger” feeling throughout the organization that we’re going to step on throats and beat teams silly and try to win every single game we play. The team is on cruise control, happy to make the playoffs and hope to get lucky. THAT is squandering. I can take losing when a team has done everything they possibly can. It happens! When you leave it all on the field and another team is just better than you then hey, that’s life. This team, as is evidenced by bringing back Aaron Boone after what has happened to the team under his watch, is kind of the perfect example of what I’m talking about.

    Squandered, big time.

    • Kiwi

      Perfectly articulated my thoughts & feelings. Management approach has filtered from very top all the way down to onfield play in my mind….lackadaisical & self-satisfied.

    • Scrillo

      Perfectly said. Couldn’t agree more.

  7. Steve

    As frustrating as it has been to watch the team prioritize the LT over championships, I am 100% giving them a pass on the “elite” Patrick Corbin.

    • Bobby

      More than fair! I put him in only because he helped the Nationals win in 2019. It felt relevant.

  8. Anthony Rizzeddardo

    Daniel Asks: Do you think that the Yankees botched and squandered this potential championship window?

    Botched, squandered, bungled, pissed down the toilet, whatever word you wanna use they did it, Daniel. I don’t care about regular season wins because those mean nothing. Ask the Packers how they feel about regular season wins. Rings are all that matters. They had a hell of a club in 2017 with a hell of a manager and for some reason they decided they needed to tear it all down and hire a weak feckless tv analyst to lead the team into a blackhole for the next five years. Girardi had them on the doorstep and without the Astros cheating they may have won that year. Boone has done nothing but take them backwards ever since. They went from Game 7 of the ALCS to the LDS and last year they couldn’t even win the WC game. It’s just a sad pathetic decline for a once proud franchise. And they had a chance to rectify it and hire Buck but let the rival Mets get him instead. And nothing will be done to make the team better despite glaring needs at 1B, SS and SP. Some washed up veteran like Jay Bruce or Kendrys Morales will be signed and that will be the major fix.

    • Christopher D Reese

      Hal is nothing like his dad. George wouldn’t stand for thus at all

  9. Haven’t even read the article yet, came straight down to say yes, they absolutely have. Winning the WS is hard and I still think they can absolutely win one in the near future. But the fact is that the Yankees could have set themselves up to win the division year after year and make perennial ALCS appearances. Every year they have been one or two pieces shy of getting over that hump (2017 notwithstanding) and every time they refuse to make the moves necessary. Whether its not acquiring a player at the trade deadline to replace someone on the IL, or not spending money on a generational player who fits your roster perfectly (looking at you Bryce Harper), this organization has shown more interest in lining the pockets of the owners while treading water and staying in contention JUST ENOUGH to not be accused of not trying. Things looked so amazing in 2016/2017 but since then its been all downhill.

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