Of course the most painful game was the one that ended the latest. It was slightly after midnight when the Los Angeles Dodgers put the finishing touches on a World Series Championship and celebrated in the house of the New York Yankees. The only good news about this outcome is that I actually get to have more than six hours of sleep. The bad news? It will be extremely difficult to get this Series loss out of my head. After all, this is the fourth straight year that the Yankees’ season has ended in embarrassing fashion.

Ryan and I were texting throughout the entirety of Game 5, long after everyone else went to sleep. To say Ryan was unhappy is a major understatement. He waited all his life to see his most favorite team play for a championship. The result he got, particularly in the clinching game, was nothing short of disgusting. From the pulling of Gerrit Cole in Game 1, to the final whiff of Alex Verdugo, it felt as though the Yankees were a JV team compared to the Dodgers fielding a varsity squad. As much as he tries to love Aaron Judge, him striking out in nearly half of his playoff at bats gives him pause on judging (no pun intended) how to rate this team since 2017. Despite the payroll, despite the talent, the franchise has consistently come up short when it mattered most. In case you have forgotten, this is how each of the last four years have ended:
2021-Wild card blowout vs. the Red Sox
2022-Swept in the ALCS vs. the Astros (lost the clincher at home)
2023-No playoffs, 82-80 record
2024-Lost the World Series in five games (again, lost the clincher at home)
Some of you reading this might say, “But at least they get to the playoffs almost every year. Most teams would kill for that”. Sorry, that’s not good enough. Talk to fans of the Milwaukee Brewers who have made the playoffs five out of the last six years with nothing to show for it. Ask Caitlyn. Do you think she is thrilled with the Phillies coming up short three straight seasons? Making the World Series in 2022 was great but these last two years have ended in frustration. Do you think those fans feel lucky?
I have my own feelings about what needs to happen to next. I don’t want to say them out loud yet because I could change my mind next week. One thing I do know is that the status quo cannot remain the same. If that means Brian Cashman and/or Aaron Boone are relived of their duties, then so be it. Their pairing as a team was good but ultimately fell short of what every Yankee fan should experience: a World Series championship.
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