Pinstripe Hopes and Postseason Woes

“Soto a high fly ball to center…Thomas backing up…Thomas at the wall…” The rest of the announcer’s call was drowned out by cheers; my brother and cousin erupted into screams over FaceTime, and my dad and I high-fived in jubilance. All of our previous anxiety, distress, and exhaustion disappeared: it was Game 5 of the American League Championship Series (ALCS), in which the Yankees had a 3-1 lead, and Juan Soto had just hit a monster three-run home run in the top of the tenth inning. As we watched him jog the bases, one almost unbelievable thing became clear: for the first time in 15 years, the New York Yankees were going to the World Series.

At various points in baseball history, the Yankees’ progression to the World Series was expected. Most recently, under players like the “core four” (shortstop Derek Jeter, pitchers Mariano Rivera and Andy Petite, and catcher Jorge Posada), the Yankees saw a dynasty era from the late 90s to early 2000s; older fans, including my father, witnessed four championship wins within five years (‘96, ‘98, ‘99, 2000), as well as the 2009 championship and two other World Series appearances (‘01 and ‘03).

My brother, cousin, and I, however, had lived through a fifteen-year dry spell. We witnessed various playoff appearances and various almost moments, but just that: our generation’s Yankees were always almost there, yet never close enough to star in the fall classic. Perhaps the earliest example of this in my time as a fan was 2017, when the Yankees made it to Game 7 of the ALCS…only to be shut out by the Houston Astros. The Yankees would lose to the Astros in the ALCS again in 2019 and 2022.

This year, however, was different—there were no Astros to stifle the Yankees’ race to the World Series. It was our year…until it wasn’t.

The 2024 World Series was supposed to be one for the ages. Not only did it revive a historic rivalry between the Yankees and the (once Brooklyn-based) Los Angeles Dodgers, but it was monumental: record-wise, it was a series between the two best teams in baseball; outfielder Aaron Judge and Dodgers pinch hitter Shohei Ohtani, the predicted MVPs of their respective leagues, would be facing off in their first World Series appearances; and the series sparked a battle between the East and West Coasts. Viewers—including myself—expected a grueling, back-and-forth, and neck-a-neck seven-game series.

Game 1 played into this illusion, with the Dodgers and Yankees going back and forth and extending the game into a tenth inning with a 2-2 tie. The Yankees then took the lead, with third baseman Jazz Chisholm Jr. stealing two bases and scoring a run off of shortstop Anthony Volpe’s ground ball. I will admit: that play finally allowed me to breathe—but just for a second. The bottom of the tenth got off to a weak start as defensive errors allowed second baseman Gavin Lux—who walked against pitcher Jake Cousins—to run to second. With two men on base, the Dodgers returned to their leadoff man, Ohtani.

Yankees manager Aaron Boone called in Nestor Cortes, a lefty starter, a decision that was questionable to many. Though Ohtani hadn’t previously faced the pitcher, proving advantageous, Cortes had been out due to an injury since September 18th; his first game back was Game 1 of the World Series. Though he was able to thwart Ohtani, Cortes intentionally walked right fielder Mookie Betts, loading the bases for first baseman Freddie Freeman. Freeman took full advantage of his position, driving Cortes’ first pitch deep into right field.

I remember the stadium erupting on my TV as my heart dropped; the Yankees’ one-run lead was no more. Freeman hit a walk-off grand slam, the first to ever be hit in a World Series game—granting the Dodgers a magical Game 1 victory. A victory marred by the Yankees’ defensive errors and managerial choices which would remain prevalent throughout the series.

Game 2 also saw an offensive struggle. The Dodgers won 4-2 as the Yankees collected only four hits throughout the game (as opposed to the Dodgers’ eight), struggling under starting pitcher Yoshinobu Yamamoto. Though the Yankees were able to load the bases in the bottom of the ninth, their efforts turned out to be futile, as they scored just a paltry run before the game ended.

Still, I—like many fans—went into Game 3 with a glimmer of hope. A 0-2 deficit wasn’t impossible to return from, and the Yankees were home at Yankee Stadium; if they could win all three games in the Bronx, perhaps they had a chance.

Yet, as Fat Joe’s subpar pre-game performance foreshadowed, the Yankees had become lifeless. Their offense struggled, with Dodgers starting pitcher Walker Buehler managing five shutout innings. Though left fielder Alex Verdugo was able to put the Yankees on the board at the bottom of the ninth, their rally was too little too late—once again. The Dodgers prevailed with another 4-2 victory, extending their World Series lead.

At this point, my illusion of a Yankees comeback was crushed. No team has ever returned from a 3-0 deficit in the World Series, and only one team has done so in any seven-series game: the 2004 Boston Red Sox in the ALCS…against the Yankees. The mention of that series still strikes fear into the hearts of fans who were there to see it, like my father.

I, like many viewers, walked into the decisive Game 4 expecting the worst: a blowout Dodgers victory and a World Series delivered to LA in the Yankees’ backyard. Freeman’s first-inning two-run home run only cemented my concerns—until Volpe stepped up to the plate during the third inning. In the previous inning, the shortstop made a base-running error, failing to score on catcher Austin Wells’ double. Fortunately, he was able to redeem himself, hitting a go-ahead grand slam.

Not only was it a breath of fresh air to see the Yankees finally take the lead, but it was extra special for this lead to come from Volpe. The 23-year-old grew up in the New York metro area as a fan of the Yankees—a picture of him at the 2009 World Series parade went viral prior to the World Series. Many children grow up dreaming about playing for the Yankees as a shortstop and having a “Jeter moment”: 15 years later, in only his second major league season, Volpe finally had his at the best time possible.

Volpe’s grand slam gave the Yankees some much-needed momentum, and they went on to win Game 4 11-4. The Yankees finally woke up, and this victory instilled just a bit of confidence in fans; while we certainly didn’t expect a championship win, we at least had hope that the Bronx Bombers could force a Game 6.

Game 5, however, was a game Yankees fans will look back on and cringe for years to come. It started off promising: Judge hit his first World Series home run in the bottom of the first and Chisholm Jr. followed, giving the Yankees a 3-0 lead. Their offense continued to flourish and Gerrit Cole pitched four shutout innings, amounting to a 5-0 lead. Finally, the Yankees were playing as a World Series-caliber team…

…until the top of the fifth inning. The Dodgers scored five unearned runs due to sloppy and, honestly, embarrassing defensive errors; Judge failed to catch a routine fly-ball, Volpe and Chisholm Jr. had a faulty throw, and Cole and first baseman Anthony Rizzo failed to cover first, fully erasing the Yankees’ lead. Though Giancarlo Stanton put the Yankees back ahead in the following inning, it was no use: the Dodgers scored two runs in the top of the eighth (on the back of yet another error), earning them the victory and the World Series championship. 

As I shut the TV off to save myself from watching the Dodgers’ celebrations (celebrations at Yankee Stadium, no less!) and commiserate with my brother, one sad truth became clear: the Yankees lost to themselves. 

The entire World Series could have and should have gone differently, but the Yankees were sloppy and reckless. Their poor defense, questionable managerial choices, and lack of focus were nothing new; in the regular season, the Yankees made 113 errors, the seventh highest in the MLB. These fundamental mistakes may not have seemed as dire to some in the regular season, especially as they were drowned out by star power and power hitting, but they became fatal in the World Series—especially against a team as strong as the Dodgers.  

That’s not to say that the season was a complete failure: the Yankees won 94 games, extending their winning season streak to 32 years; they took the AL East title; they made their 59th postseason appearance and won their 41st AL pennant; and they made it to the World Series for the first time in fifteen years. Rather, watching the team waste their potential was disheartening.

Not only that, but the team has conditioned fans to have a “World Series or nothing” mentality in their chase for twenty-eight. We are expected to hold these Yankees to the same standards as those of the 90s and 2000s, yet year after year we are disappointed: the two eras are not the same. The Yankees need to prove their place, rather than relying on a legacy that long precedes them. Serious changes need to be made. For one, management needs to emphasize fundamentals. Errors like those in Game 5 cannot happen on the big stage. 

Furthermore, managerial mentalities need to change. It’s fruitless to continue playing the same way season after season—loss after loss—and expect something to miraculously change. Aaron Boone, seemingly returning for the 2025 season, has been the Yankees’ manager for 6 years (since 2018), and the team has only made one World Series appearance in this time. 

The Yankees also need to work during the off-season and fill in the gaps in their lineup. Of course, much remains up in the air, with one question weighing down on most fans: the fate of Soto. The outfielder is one of the most highly sought-after free agents in the offseason, and it’s difficult to tell whether or not the Yankees will be able to bid high enough to keep him. 

All this being said, all hope isn’t lost. Though the first Yankees World Series of my lifetime didn’t go as I had dreamed it would, it proved that my generation’s Yankees can make it to the World Series. Not only that, but young players—like Volpe—are a beacon of hope for the Yankees’ future; with further training and experience, they might just become unstoppable. In fact, I believe that, with some team-wide reevaluation and reorganization, the Yankees can take it all. It won’t be easy, nor will it come immediately, but it’s possible—and that’s all that matters. Until then, I’ll remain tuned in for every game, no matter how much they make me want to pull my hair out.