The 2025 season has come and gone for the Yankees. There were plenty of highlights, as Jeremy showed yesterday, but there were also plenty of lowlights.
Today, we will, unfortunately, look at those lowlights
in Pinstripe Alley’s annual installment of the worst moments of the 2025 season.
(Dis)honorable mentions
- Multiple Devin Williams meltdowns: A few Toronto games, the four-run fiasco against the Rays in April, etc. Thankfully he ended his season as a trustworthy setup man, because it got ugly for a while.
- June 18th vs. Angels: After finally snapping a three-game shutout streak in the midst of a brutal six-game skid, Anthony Volpe boots a potential double play ball in the eighth to allow the Angels to take a 3-2 lead.
- July in the Rogers Centre: The Yankees lost the AL East and likely sealed their fate in the ALDS with a horrific 1-6 record on the road against the Blue Jays in July that featured over a dozen defensive miscues, blowup starts, a torn UCL, and back-breaking blown leads.
- September 3rd at Astros: An absolute ump-show in Houston. Williams gets squeezed, Camilo Doval gets a phantom balk called, and Jazz Chisholm Jr. gets rung up on a pitch outside with a chance to bring the go-ahead run to the plate. One of the worst umpired innings of the season.
- Wild Card Series Game 1 vs. Red Sox: Luke Weaver implodes in the seventh to ruin Max Fried’s brilliance and the Yankees get the tying run into scoring position in the ninth against Aroldis Chapman with nobody out, only to strand the bases loaded. If not for Cam Schlittler’s Game 3 heroics, this would be higher.
5. Gerrit Cole goes under the knife
There was no injury more soul-crushing for the 2025 Yankees than Gerrit Cole undergoing Tommy John surgery. The 2023 AL Cy Young Award winner had recovered from an elbow ailment that cost him several months in 2024 in advance of a great playoff run, giving it his all even as the team collapsed around him in Game 5.
Losing your ace before the season starts hurts. What hurt more was that it was compounded with a shoulder injury to Luis Gil that kept him out until August and Clarke Schmidt starting the season on the injured list due to a late ramp-up before eventually undergoing Tommy John himself in July. That required the Yankees to give 15 starts to the over-the-hill combination of Marcus Stroman and Carlos Carrasco while relying every fifth day on rookie Will Warren — a fine No. 5 starter, but one who certainly took his share of lumps. It’s safe to say that a Cole injury put the Yankees in a hole to start the year that they had to climb out of.
4. Joc Pederson, Josh Jung sinks Yankees to rock bottom
August 4th
Unlucky recapper: Nobody*
*This game coincided with SB Nation’s site shutdown as we transitioned to a new, fresher layout. Safe to say, this was the perfect game to take the night off.
There are a few moments that could be described as rock bottom during the Yankees’ dreadful summer swoon, but this one rings eternal. After an embarrassing sweep in Miami (more on that later), the Yanks went to Arlington and looked to right the ship. For eight innings, it looked like they would. Max Fried battled through five innings in the midst of his midseason struggles, but the Yankees hung five runs on Patrick Corbin and Jon Gray in four innings.
Clinging to a 5-4 lead after eight, Williams got the ball. After inducing a quick groundout of Kyle Higashioka, he faced a pinch-hitting Joc Pederson, who entered the night with a woeful slashline of .126/.256/.217. While he finished the year strong, a case can be made that at this point, he was the worst hitter in the majors. Of course, he crushed an in-zone changeup to tie the game.
As if that’s not bad enough, the Yankees went scoreless in the top of the tenth and turned it over to Jake Bird. The newly-acquired reliever retired the first two he faced, intentionally walked Wyatt Langford, and then didn’t get a sinker inside enough on Josh Jung, who crushed a walk-off home run to left field. This would be Bird’s final appearance of the season, as he spent the last two months banished to Triple-A.
The moment was bad, but when you compound it with everything else? It was devastating. After getting shut out the following night, the Yankees fell to just 0.5 games ahead of a wild card spot, as close as they’d come to meeting the fate that another team with a $300 million payroll would endure.
No. 3. The start of the Summer Swoon
Unlucky recapper: Estevão
The game itself left a sour taste in everyone’s mouth, but the symbolism of it being the start of the now-yearly summer swoon is what puts it on this list. First, let’s recap the game.
Garrett Crochet did Garrett Crochet things. The Yankees tried their best to match him with Ryan Yarbrough, and they fared pretty well, with him and the bullpen holding the Red Sox to one run in eight innings. Still dazzling in the ninth, Crochet went to a career-high pitch count to finish off a shutout, but Aaron Judge stood in his way. On a triple-digit heater, on pitch No. 107, Judge pounded it out of Fenway Park to tie the game.
After Fernando Cruz and Tim Hill combined to toss a scoreless ninth, shenanigans ensued. Anthony Volpe got thrown out trying to steal third in a bang-bang play that was ultimately overturned on review. MLB’s “too close to overturn” doctrine was applied very inconsistently here, as while that was apparently not too close to overturn, DJ LeMahieu’s ensuing foul ball—which may or may not have touched the foul line—was too close. That’s to say nothing of the fact that it clearly passed over the bag (which is a judgment call), and LeMahieu got tossed a few pitches later. Anyway, Tim Hill allowed a walk-off single to former Yankees catcher Carlos Narváez off the Green Monster in the bottom half.
That night was the beginning of the team’s horrific 20-31 stretch that wound up costing them the AL East and No. 1 seed, something that might’ve been nice to have based on how the season ended.
2. Blue Jays escape sixth inning in Game 1
Unlucky recapper: Matt
The final score of this one was 10-1, so you might think that this doesn’t deserve to be here. However, I believe that the Yankees would’ve managed this game differently with a lead, especially knowing Max Fried was on the bump the next day.
The Blue Jays had a 2-0 lead after five innings in Game 1, powered by solo jacks by eventual playoff hero Vladimir Guerrero Jr. and surging catcher Alejandro Kirk. Kevin Gausman had completely silenced the Yankees, tossing five shutout innings on just 50 pitches. In the sixth, though, things changed.
Anthony Volpe doubled, Austin Wells singled, and Trent Grisham walked. The bases were juiced with nobody out. The tying run was in scoring position for the heart of the order, including Judge. Judge worked the count full against Gausman and got a 3-2 splitter way out of the zone that could’ve been an RBI walk. Instead, Judge whiffed.
This was really the one time this postseason that Judge fell short, as he exorcised some demons with a 13-for-26 showing and a 1.273 OPS in 31 PA … but this still hurt. (At least he had Game 3.)
Cody Bellinger then drew a bases-loaded walk, but Ben Rice and Giancarlo Stanton stranded the bases loaded against Gausman and Louis Varland. After this, Weaver would implode in the seventh, and Cruz couldn’t stop the bleeding. With a lead, are we sure Weaver ever enters this game? If the Yankees led, they could’ve gone with Cruz, Williams, and David Bednar to steal Game 1. If you’d rather bemoan the final, deflating Game 4 loss instead, that’s justified, but it’s entirely possible that stranding the bases loaded was what doomed the Yanks from the start.
1. A post-deadline catastrophe
Unlucky recapper: Estevão
There was no bigger shift in vibes throughout the Yankees’ season than there was in the last week of July. A month and a half into their summer swoon, the Yankees took three out of four against the Rays after Judge’s elbow scare nearly sent the entire organization into panic mode. Not just that, but the Yankees were wheeling and dealing at the deadline, acquiring four new players on the final day, including three relievers to repair a shoddy bullpen.
The first game after the trade deadline was in Miami, where the Yankees looked to be coasting with a 6-0 lead in the fifth. After four shutout innings by Carlos Rodón, he began to collapse. Javier Sanoja, who had just one MLB home run, hit a two-run shot. Two more walks chased him from the game, and Jonathan Loaisiga struggled in relief, plunking Otto Lopez to load the bases and allowing a two-run single to Liam Hicks, making it 6-4.
In the seventh, Grisham smashed a three-run homer to make it a five-run game. The Yankees also had bases loaded later in the inning. Crisis averted, right? Nope. Bird came on for his Yankee debut and he struggled badly, giving up a back-breaking grand slam to Kyle Stowers in the bottom of the seventh, making it 9-8.
Bednar came in for his Yankee debut after and, two batters later, coughed up another home run to Sanoja. Two of Sanoja’s six home runs on the season (in 342 PA) came in this game, and it was Bednar’s first blown save and first home run allowed since May 23rd. Tie game. A double, a single, and an RBI single by Agustín Ramirez made it 10-9, Marlins.
But, once again, the Yankees rallied. Anthony Volpe blasted a game-tying home run to lead off the eighth and hit a clutch RBI double in the ninth to help the Yankees go up 12-10, handing the ball to the third reliever acquisition, Camilo Doval.
Doval got the first out, but the Marlins put the tying run on base quickly after. This is where the fourth player the Yankees acquired comes into play. José Caballero, a utilityman who offers great defense in the infield and outfield, pinch-ran for Rice in the ninth and made his Yankees’ debut in right field. On an ensuing single by Xavier Edwards that would’ve only scored one run, Caballero let the ball roll under his glove for a game-tying error that put the winning run on third. Shortly after, a swinging bunt by Ramirez left Wells helpless, and the Marlins walked it off.
It was as stupid as it gets. All four players acquired the day prior completely imploded, and although Caballero and Bednar would eventually become fan favorites, it left a sour taste in everyone’s mouths for a while.
