A recording of Game 5 of the 2025 World Series still sits on my DVR, but not because there’s any danger I’ll ever forget it. The truest words that Yankee manager Aaron Boone has ever spoken came in the aftermath of that game when he emerged bleary eyed from the clubhouse to face the media and answer questions about one of the most shocking defeats in the long postseason history of the greatest franchise in sports.
“As I said to the guys, obviously it stings now. This will sting forever.”
I said something similar to my wife the next day as I was trying to put my life back together. “As long as I live, I will never get over that game last night.”
I could say that confidently because twenty-four years later I still haven’t gotten over Game 7 of the 2001 World Series, and I still wear the scars of the last four games of the 2004 ALCS. Keep in mind, my connection to this organization is measured only by the dozens of Yankee caps I’ve worn over the past 47 years, the seven World Series titles I’ve celebrated, and the thousands of games I’ve watched. This team is a part of me, so obviously losses like these are more than just disappointments.
But I’m at least self-aware enough to know that I don’t really know. I can’t possibly know what it feels like to begin working with a purpose in January, report to spring training in February, ride busses across Florida in March, endure the trials and tribulations of a six-month regular season, and then fight through two playoff rounds in October only to have the journey end in the most inexplicably painful way imaginable.
What I do know is that there are coffee mugs and mouse pads and t-shirts with the FOX chyron from that fateful top of the 5th inning, souvenirs that celebrate one team’s devastating collapse rather than the other’s improbable comeback. I know that I’ve catalogued the comments and asides I’ve gotten from Dodger fan friends and family here in Southern California, each remark innocent in its delivery but cutting nonetheless.
But I can’t know how many times Aaron Judge has thought about that dropped fly ball or how he will feel when he inevitably gets a sarcastic standing ovation before his first at bat at Dodger Stadium on Friday night. I can’t know how often Nestor Cortés has replayed the pitch he threw to Freddie Freeman, or whether or not Gerrit Cole had flashbacks during PFPs in spring training.
Will those demons get in the way during these three games, or will they drive the team to success over the weekend and through the rest of the season? Paul O’Neill frequently reminds us that the white hot brilliance of 1998 might never have happened had it not been for the October disappointment of the year before, so maybe we’ll see something similar this year. Maybe.
But I don’t think we’ll get an answer to that this weekend. Instead we’ll get constant comparisons of Judge and Shohei Ohtani, frequent reminders of last October and some of the more distant Octobers, and breathless predictions of another matchup in this year’s World Series. And we’ll probably get some good baseball.
And me? At some point I’m sure I’ll check my DVR and navigate to the folder titled “L.A. Dodgers @ New York Yankees.” I’ll watch the first inning as Judge hits a rocket into the right field stands and the crowd explodes with relief, I’ll watch Jazz Chisholm follow with a home run of his own, I’ll scan ahead to Stanton’s bomb in the third, and I’ll remember how it all felt. But then I’ll watch the fifth inning, and I’ll wonder what might have been.
[Image Courtesy of Wikimedia Commons.]


