
With the Yankees’ season over for 2026, we here at Pinstripe Alley have been looking back at the campaign. With how it ended, a lot of our coverage has come through a lens of frustration, but we’ve looked back at some of the good and bad all the same. However, now it’s time to look back on some pure stupidity.
We’ve ranked things like the best and worst moments of the year. We’ve talked about some of the best individual performances of the season. However, I am a connoisseur of stupid baseball: games that go 15 innings, ones that feature game changing plays that are ridiculous errors instead of home runs, stuff like that. Every year, I like to take part in our end-of-season reviews by ranking the dumbest games of the year, and we’ve reached that point for 2026.
Now, it should be noted, this is not a worst games of the season list (or worst moments; check out Andrés for that). We’re not just ranking the most consequential losses, or biggest blown leads, or whatever. This is purely the games that were the dumbest in how they played out.
Honorable Mention
It didn’t feel right putting it in the rankings since there was no baseball actually played, but we’ll give a mention to the rainout on the final day of the regular season. With a nor’easter wreaking havoc and the game not meaning anything in the standings for either the Yankees or Orioles, it was obvious this game was never actually going to be played. However, the game was put into a delay and just stayed there for hours until it was finally called off. The Yankees never even actually released a lineup. Ridiculous.
5. September 25th – Orioles 10, Yankees 2
The aforementioned nor’easter messed with the entirety of the final series of the season, which had an impact on some other events. The Yankees were planning on holding the ceremony for CC Sabathia’s number retirement ahead of the game against the Orioles on Saturday, September 26th. However, the expected rain led to the teams instead forgoing Saturday’s game in favor of a doubleheader on Friday. The new plan was to hold Sabathia’s ceremony ahead of the opening game of the twin bill (in accordance with his wishes). However with it now being an afternoon game on a weekday, the crowd was not remotely as full as it could’ve or should’ve been for a moment like that.
Plus, when the game started, the Yankees got absolutely blown to smithereens. The Yankees gave Brendan Beck a spot start as they prepared for the postseason, and he got smoked for seven runs in five innings. We honestly weren’t far away from seeing if CC himself could eat some innings out of the bullpen.
4. August 3rd – Cardinals 13, Yankees 7
After a rare bad outing from Cam Schlittler, the Yankees found themselves down 6-0 going into the bottom of the fifth. Back-to-back homers from Austin Wells and Trent Grisham cut into the lead, but they still trailed in the seventh. There, a trio of homers brought the Yankees all the way back, with a two-run moonshot from Luis García Jr. give the Bombers a very unexpected lead.
However, the good vibes from that comeback only lasted so long. Ryan Yarbrough allowed a triple to lead off the eighth, at which point Angel Chivili came in. Chivili’s final numbers for the season only look so-so, but that’s almost entirely because of this game. He had a 0.57 ERA in 15.2 innings coming in and wouldn’t appear again after this performance (at least partially due to injury). In this game, Chivili allowed seven runs on six hits, including three home runs. In one inning of work, he put up a -0.512 Win Probability Added. Losing games after big comebacks happen, but rarely do they happen in such an immediate and drastic way.
3. ALDS Game 1 – October 3rd – Rays 1, Yankees 0
As I said, this isn’t purely a ranking of the most meaningful losses, but as it happens, one of those was also especially dumb. After crushing the Red Sox in the Wild Card Series, the Yankees then went to the Trop to take on the Rays. They then proceeded to get no-hit into the eighth inning by Rays’ ace Drew Rasmussen. Plus, when they finally did get it hit on an Austin Wells double, this happened, and it ended up being the only one they got:
2. July 29th – White Sox 6, Yankees 5 (12 innings)
In general, I’m not one to truly hate on a Yankee player. Sure, there are some bad ones that pop up every now and then, but usually any anger I have is to the front office/management for putting them in bad situations, rather than hating a player who is generally trying their best. However, one particular play made me something of a hater when it comes to backup catcher Ali Sánchez.
In one game in Chicago against the White Sox, the Yankees had already blown a late lead, sending it to extra innings. In the 11th, they got the lead back thanks to an Anthony Volpe sacrifice fly. In what turned out to be his final game as a Yankee, Camilo Doval entered for the 11th and got two quick outs, albeit one was a grounder that did allow the auto-runner to move to third. However, the Yankees were just one out away, and all they had to do was focus on Andrew Benintendi at the plate.
Someone apparently forgot to remind Sánchez that. Following a pitch during the next at-bat, he attempted to check back Munetaka Murakami at third. However, his throw got past Ryan McMahon, allowing Murakami to come home and tie the game.
Errors happen to even the best players and best defenders, yes. However, what was so galling about that one was that — to use a tennis term — it was unforced. Again, they were an out away from the win, you just needed to focus on the batter. Sure, throw to third if you catch the runner completely sleeping and a mile off the bag, but that wasn’t the case. The risk was too much considering the consequences if it went wrong, and it went very wrong. Naturally, the White Sox proceeded to win the game the following inning.
1. September 16th – Twins 5, Yankees 4 (13 innings)
The Yankees’ struggles in extra innings since the introduction of the automatic runner are often remarked on. Since that rule was introduced in 2020, the Yankees have gone 49-54 in extra inning games. While that’s not that far under .500, they actually went 25-18 in extras from 2020-22, so they have just a .400 winning percentage since then. They’ve also been the second-worst road team in extras in this time at 19-36. Arguably no game epitomizes those struggles than this one.
Having been shutout for eight innings at Target Field, the Yankees somewhat miraculously tied the game with two outs in the ninth on a two-RBI double from Anthony Volpe. Mind you, a lot of us, including Volpe himself, thought the ball was going over the fence for a two-run homer. However, it didn’t and the Yankees couldn’t score Volpe, sending it to extras.
In the top of 10th, Ali Sánchez, of all people, came up with a single to score the auto-runner and give the Yankees the lead. Despite having closer David Bednar on the hill, the Yankees couldn’t close the deal as Luke Keaschall hit a game-tying single on just the third pitch of the inning, and Bednar eventually needed a double play to escape the inning.
However in the 11th, José Caballero hit a sacrifice fly to restore that lead. Surely, they could hold on this time? No, Bednar again allowed a lead-off single, with a run then scoring on a Royce Lewis sacrifice fly.
To start the 12th, the Yankees put the first two runners on, adding to the auto-runner to load the bases. However, a Heliot Ramos double play and a Sánchez groundout caused the Yankees to put up a goose egg. Eventually all of that came back to haunt the Yankees. In the 13th, Victor Caratini singled off John Schreiber to win the game for the Twins.
This was also the game where Aaron Judge exited early with a calf injury, from which he never returned.
It wasn’t the most meaningful loss of the season — although with the Yankees still trying to chase down Tampa Bay in the division, it wasn’t nothing — however, it absolutely was the most ridiculous.
That’s my list, but what else should be on there?

















