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The stupidest Yankees playoff games of the past 25 years

We’ll be remembering some wonderful playoff memories over the next couple weeks, so let’s humble ourselves a bit.

New York Yankees v Cleveland Indians

Back on Monday, we here at Pinstripe Alley began a series looking at the 25 best Yankees playoff games from the past 25 years. Considering how often the Yankees have made deep runs in October in that time, there’s plenty of good games to choose from, and we’re going to have fun looking back through them.

However, not every playoff appearance has ended in championship glory. In fact, to the consternation of many of us, it’s been a while since the Yankees have even appeared in the World Series. That means that while there’s been many great wins over the last 25 years, there’s also been some very annoying ones in that time.

As we remember the successes over the years, let’s also take a look at the stupidest playoff games from the last 25 years to drag us back to earth a bit, obviously with the exception of 2004, since it was so weird that they just cancelled the season after the Yankees went up 3-0 in the ALCS. This post is not necessarily about the worst or most painful losses. We’re just talking about sillyones.

5. 2022 ALCS Game 3

A fairly new addition to this list, but it certainly earned it. After getting no-hit by Cristian Javier and the Astros bullpen in a June game at Yankee Stadium, it seemed like the 2022 Yankees were en route to doing it again in the Bronx during a must-win ALCS Game 3. It didn’t end up taking that long into the game before Giancarlo Stanton’s fourth-inning double, but with the vibes already in the toilet, it felt more like Javier was on the verge of doing it again. The Yankees only managed three hits in the game, which was far too few to get a win and keep any genuine chances alive.

This one might be recency bias, but it felt pretty galling to watch in the moment.

4. 2006 ALDS Game 4

Speaking of vibes, being in the toilet: this game! After splitting the first two games in New York, the Yankees were blanked in Game 3 in Detroit by Tigers starter Kenny Rogers — a man who had an 8.85 career playoff ERA in nine previous games. Alex Rodriguez’s struggles were especially notable, to the point where Joe Torre dropped him down to eighth in the order.

You’re not going to believe this, but that didn’t improve things.

A-Rod went 0-for-3, the Tigers pounded the hopeless Jaret Wright, and the Yankees lost 8-3, with all three runs coming in the late innings when they were already down big.

3. 2007 ALDS Game 2

This one only needs one word to describe it: midges.

2. 2017 ALDS Game 2

The 2017 Yankees were definite underdogs to the 102-win Cleveland team in the ALDS, but led by a rookie Aaron Judge, they were a fun young team who was dangerous. They showed that in Game 2 of the series as they jumped out to an 8-3 lead, looking to level things up. Then the sixth inning happened.

Starter CC Sabathia would exit the game after starting off that inning with a walk and a lineuout. Chad Green came in and got a second out, but then allowed a double that put two runners in scoring position. Next up was Lonnie Chisenhall, who was ruled to have been hit by a pitch that just seemed to graze his bottom hand. Except that on closer look, it really seemed like it hit off the knob of the bat and not his hand. Despite multiple Yankees players immediately looking at the dugout to tell them to challenge the play, manager Joe Girardi opted not to. Naturally, Francisco Lindor then immediately hit a grand slam, getting Cleveland within a run.

Sure, maybe it was possible that a replay review would’ve deemed the call too close to overturn, but it really looked definitively not a hit-by-pitch. With the stream rolling in their favor, Cleveland would later tie the game before winning it in 13 innings. The Yankees would somehow muster a series comeback and win it in five, but Girardi failing to challenge that HBP call seemed like the death blow in the 2017 season when it happened.

1. 2018 ALDS Game 3

The Yankees were feeling pretty good about things after splitting the first two games of the best-of-five series on the road in Boston. The win meant they had a chance to take the series at home if they could hold serve in Games 3 and 4. Oh boy, did that extremely not happen.

After possibly getting the wrong start time and not warming up until very close to first pitch, Yankees starter Luis Severino struggled. He allowed a run in the second, two more in the third, and then was finally pulled after loading the bases to start the fourth. Lance Lynn replaced him, but that arguably went even worse. He only got one out in four batters before Chad Green was sent in. When the dust settled in the inning, the Yankees were down 10-0, and that was basically it for the game.

That wasn’t the end of the Red Sox onslaught either. Things got so bad that the Yankees went to the position player well and brought in Austin Romine to pitch the ninth inning. That was the first, and so far only, time that a position player has taken the mound for the Yankees in the postseason.

The final score ended up 16-1, and it’s going to take a truly horrendous performance to ever top it.