This era of the Yankees never gets the last laugh

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The crushing end to this year's World Series shows again this era of the Yankees' struggles to punch back when push comes to shove.

Having been born in 1991 and with my first sports memories of any sort being the 1996 postseason, my life as a Yankee fan hasn't been too bad. I've gotten to see five World Series titles, a couple other AL pennants, and countless big games, plays, and memories.

Even in some of the years where the Yankees came up short, I still treasure some games. I'm talking like the heroics of Games 4 and 5 of the 2001 World Series, Aaron Boone's home run in 2003 — even if it has partially led to his often frustrating tenure as Yankee manager. As sad as the endings to those various runs were, I still love those particular games and moments.

While we're still in the raw aftermath of the Yankees 4-1 loss to the Dodgers in this year's World Series, I can't help but think that there aren't really any moments from this run that I'm going to have those emotions for. Juan Soto's ALCS-clinching home run was undoubtedly cool and a hell of a feat, but my immediately feeling is that it won't quite hit the same as something like the Derek Jeter "Mr. November" homer.

Part of that is probably due to hindsight and the fact that the Yankees won several other World Series titles in that era allows me to look wistfully at stuff that didn't lead to one. Perhaps if Soto returns and helps the Yankees to a title or two or three then my opinion will change. However, my worry in the days after this World Series is that the reason I don't feel that way is because I don't trust this era of the Yankees because they never seem to get the last laugh.

I'm not going to go into WFAN caller mode and start calling them "mentally weak" or say that they need to fire everyone and hire a manager that comes in and screams at them all the time. (Wouldn't be opposed to a managerial change at the very least, and would prefer a new GM in place of Brian Cashman too, but that doesn't look likely, so whatever.) However, I just can't get rid of the suspicion that the vibes of this team just quickly go down the toilet when they get punched in the face.

In 2018, the Yankees put up an excellent regular season that was just bested by a better Red Sox team. They got a chance to face off against Boston in the ALDS, and went in and split the first two games on the road. After their Game 2 win, Aaron Judge was spotted playing "New York, New York" from a boombox as the team headed out of Fenway Park. The Yankees then famously lost Game 3 16-1 and went out in four games. The Red Sox clearly used the boombox incident as motivation, winning that matchup and the World Series, even playing "New York, New York" in their post-championship celebrations.

In 2020, the Yankees and Rays had some heated words for each other. After Aroldis Chapman buzzed Mike Brosseau with a pitch in a late regular season game, Tampa Bay manager Kevin Cash took great umbrage with that, saying after that game that he had a "stable of guys who threw 98," semi-warning the Yankees after an incident they believed was intentional. While nothing ever led to fisticuffs, that season ended with Chapman allowing a home run to Brosseau to allow the Rays to best the Yankees in a do-or-die Game 5 in the ALDS.

Even in less high stakes incidents, the Yankees often can't get the last laugh. In a 2021 game against the Mets, Francisco Lindor took exception to some whistling coming from the Yankees' dugout, believing they might be stealing signals. After Giancarlo Stanton hit a game-tying home run later in that game, he made a whistling motion towards Lindor, causing tempers to flare and benches to clear. How did that game end? Naturally, Lindor hit an eighth-inning homer for his third of the day, giving the Mets a lead they held on.

Add in the Yankees' constant struggles and playoff frustrations at the hands of the Astros, this era of the team has so often gotten their bluffs called, and then can't do the same in return. To be fair to them, two instances of them sorta doing that just happened this year. They held up after Jazz Chisholm Jr.'s comments about how the Yankees were better than the Royals and were going to win the ALDS despite splitting the first two games at home. They did that semi-comfortable. The ALCS Game 3 loss following the ninth inning homer from Jhonkensy Noel was one of the more brutal ones in Yankees' history, but they rebounded to take the next two games and the series.

Frankly, I don't know what the fix is. If I could add anyone from baseball history to this roster, I think I would pick some like Rickey Henderson. Some with bravado and the skill who could say "F*** you, I'm better than you" and then go out and actually prove it. However, a prime Rickey Henderson isn't walking through that door. Besides re-signing Soto, they need to make some other moves to have a realistic shot at taking that final step. I just hope they can figure out what those are, because I want to have the last laugh again.

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