SSTN Not The Weekly Mailbag: Raw 2026 Post Mortem

By Andy Singer

October 9th, 2026

I suppose that I shouldn't be surprised by the way this season ended. My brain knew that the Yankees were plagued by the same underlying issues from every Yankee team since 2019 has suffered. I knew that in a close, pressure situation, the team might fail at very basic baseball. I also knew that the success of the offense would likely be based on the performance of a few, rather than getting contributions, however small, from large sections of the lineup. The lineup was also missing Aaron Judge. All of these factors were working against the Yankees.

However, I also believed this team was good enough in other ways to overcome those very elemental deficiencies. I thought that the Rays would be the Yankees' toughest test in the American League. If they could have played well enough to allow their roster to overpower the Rays, I thought they'd march to the World Series. Clearly, that was too much to ask. I am disappointed; very disappointed. I know that some fans have described themselves as numb or apathetic regarding the Yankees' continued losing ways in the playoffs, but I don't feel that way. It still hurts. At my root, I remain a fan - I want to see the team succeed.

I have a lot of thoughts about the end of the season that I want to get off my chest in an unstructured format in such a way that a Mailbag doesn't allow. I know I promised a return this week, but I'm pushing it back one more week (don't worry, it'll be a long one; we've had a lot of Mailbag questions the last couple of weeks). Keep sending your questions to SSTNReadermail@gmail.com, and I'll work it into the schedule over the next two weeks. Without any further ado, let's get at it:

• First and foremost, congrats to the Tampa Bay Rays. They were clearly the better team this year, and I think that they would represent the American League admirably in the World Series. Despite their records, I actually don't think the Dodgers or Brewers are significantly better than the top teams in the AL. Let's see if the Rays can move on.

• Saying the Rays had a better team is not the same thing as saying that the Rays had the better roster. Over the last two weeks, people in my life asked me about what I thought about the Yankees' chances in the playoffs. Each time, I responded that the Yankees had the best roster, on paper, in the American League, even without Aaron Judge healthy. However, I also noted that I really worried about the Rays because they played tight baseball and likely would not beat themselves under pressure. Those statements in and of themselves are insane indictments of a coaching staff that has had nearly a decade to figure out how to get the best out of its players, and has simply failed on the biggest stage over and over again.

• I recognize that there's a lot more to Brian Cashman's job than just building a roster, really I do. I also know that most of us realize that Brian Cashman, while being enabled to spend a lot of money, is often stuck rarely given the ability to stretch his budget the extra bit he needs to really "Boone-proof" the roster. Again, that statement tells us where a significant amount of the issue lies. I genuinely believe, despite its flaws, the Yankees had one of the 3 or 4 best rosters in all of baseball. I also do not believe that the Yankees were one of the 3 or 4 best teams in all of baseball. Rosters can be built on paper; teams are built by culture, accountability, overcoming adversity, and a continued group effort to lift the play of those around you. That culture cannot be built from outside of the dugout, no matter how much we scream about the front office or ownership. As far as dugout culture is concerned, the buck stops with Aaron Boone. That's his job. Even if we pretended Boone wasn't responsible for the lineups (newsflash: he is, but let's pretend for half a second), does anyone think Boone's job isn't to ensure clubhouse culture is strong and that his team is ready to play sound baseball? At that job, Boone has come up resoundingly short.

• I am sure there are things Boone does well behind the scenes that we do not see. Players continue to go to bat for Boone. While we've seen some cracks in recent months, I think it's likely that players like Boone. I think the media likes Boone. Heck, I think he seems like a really nice guy, and he might even be able to learn from his time with the Yankees. But he's also proven that even with continued chances, he can't fix the underlying issues that ail the team year after year. I think Boone found a way to elevate the team in 2018 and 2019 even if his ability to manage X's and O's left a lot to be desired. He hasn't found the same formula in the years since.

• I think the biggest argument for dismissing Brian Cashman is his continued insistence that Aaron Boone is the right manager for this team. We have multiple points of emphasis, particularly since 2024, to show definitively that Aaron Boone can't get this team over the hump. What more evidence is needed? Really. The roster has churned significantly since 2024, the last time the Yankees embarrased themselves in the World Series, yet we're watching the same baseball game in the playoffs every year. That's not roster construction, that's the dugout.

• At some point, it's time for Hal Steinbrenner to come out of the hole he's been hiding in for the entire year (I suspect he's one of Manfred's minions leaking asinine CBA bargaining points to the media that have zero chance of flying). Ultimately, he needs to answer for the product that's been out there under Boone's stewardship. Dugout culture starts with the manager, but organizational culture flows from the owner. I think both cultures need real work.

• Saddest of all: I think the Yankees wasted the best rotation I've ever seen. I don't say that with any sense of hyperbole. We can use a variety of metrics to evaulate it (and I'll put it into context in the coming weeks), but this rotation was phenomenal, and it deserved to be remembered as such by baseball fans as a World Series rotation.

• Let's talk a bit about the games themselves. The Yankees telegraphed their performance against the Rays in their obliteration of the Red Sox. Even as they overpowered the Red Sox, the signs of sloppy play were there. Trent Grisham was again lazy chasing after a fly ball, and when it bounced, he was slow to play it back into the infield, allowing the runner to reach second base on a play that never should have been more than a single. Ben Rice rounded third base and was thrown out at home in Game 2. The ball came back into the infield as Rice rounded third. It was an absurdly dumb mistake, one good teams don't make.

• The last game against the Rays was infuriating for a number of reasons. The Yankees altered the lineup, something that was necessary after two listless games. Boone decided to turn to Trent Grisham as his leadoff hitter, ahead of Ben Rice who was hotter than the sun throughout the playoffs out of the leadoff spot. Grisham hasn't hit since he hurt his hamstring the first time in June. Predictably, the last at-bat of the season was a Grisham strikeout with a runner on, leaving Ben Rice in the on-deck circle.

• I noted before the playoffs that I didn't think Ryan McMahon deserved starting spot in the lineup. He hadn't hit all season and his defense, once his calling card, had regressed significantly. Either Caballero or Volpe were better choices. Many disagreed with me. McMahon was awful against the Rays. He didn't hit and he made a critical error in Game 2. The combination of Caballero and Volpe was superior defensively in Game 3. Sometimes, the right answer is obvious.

• Carlos Rodon was the Yankees' second best pitcher coming into the playoffs, and the Rays struggle against lefties. Of course, he never pitched. This was a criminally bad decision. I thought Rodon deserved to pitch over both Cole and a clearly diminished Max Fried.

• I give Max Fried gobs of credit. His elbow hasn't been healthy all season, and he still gutted through it to get critical outs. Boone left him in too long in Game 3. He was clearly laboring and struggling to locate his stuff. I hope Fried can heal up in the off-season.

• Austin Wells hit so much better in the 2nd half and also had a huge hit in Game 1. His absolutely mind-numbingly bad baserunning decision set the tone for the series. This is a baseball feel issue, but it also clearly went against the analyitics the Yankees supposedly teach. There were 2 outs. The run expectancy of a runner on 2nd or 3rd with two outs is negligible. Again, this is a coaching issue. Wells should know better, but the Yankees' coaching staff clearly didn't prepare their players for that moment.

• There will be significant changes next year. I hope it's not just the roster.

• I'm going to harp on the difference between good teams and good rosters all off-season. I really believe that not enough Yankee fans are distinguishing the difference.

• For now, I'm sad. I'll miss Yankee baseball. I really hope that Aaron Judge doesn't become Donnie Baseball 2.0. I think he's very much in danger of that happening.