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OTM Roundtable: Worst moment as a Red Sox fan?

Tim Wakefield leaves game Photo by Doug Pensinger/Getty Images

This is a week at SB Nation in which we are looking back at all of the various moments in sports that have made us cry, and as such I thought it made sense to look through that same sort of lens for our staff roundtable this week. So, for this edition’s question I asked the staff, “What was the most upsetting moment for you as a Red Sox fan?”

Shelly Verougstraete

The most upsetting moment for me as a Sox fan was seeing the team trade away Jon Lester. At the time, I knew they were at the bottom of the AL East standings with a 48-60 record but, Lester (and Gomes) for Cespedes and a competitive draft pick? Seriously?! Then, during the offseason, you don’t give him a competitive offer and see him go to the Cubs? Yes, I know Lester has been pretty mediocre at times the last few seasons but he was our guy. I don’t think I’ll ever be comfortable seeing Lester in a Cubs uniform, even after all this time.

Mike Carlucci

With all due credit to the 2003 ALCS, the most upsetting moment for me as a fan was 2004 ALCS Game 3 when Joe Buck and Tim McCarver named Hideki Matsui ALCS MVP. I don’t remember what the score was at that time, but it might have been as soon as his home run off Bronson Arroyo. I had missed parts of Games One and Two with class but for Game Three, I was ready. Two college roommates - one a Yankee fan always politely clapping at their hits, the other a Red Sox fan who made his own Trot Nixon-style dirty hat - were there to watch. We were all excited for a good game, at the very least, despite knowing our rival was the winner if our team lost. At least 19 times my roommate clapped and cheered while we became more and more silent and depressed. For all the joy and happiness that was soon to follow, that game was painful and awful. 2003 happened in an instant. Game 3 happened over hours.

Phil Neuffer

I’m not really sure how the answer for anyone my age can be anything other than Aaron Boone’s walk-off home run in game seven of the 2003 ALCS. That entire sequence is still burned into my mind and that’s after four subsequent World Series titles for the Red Sox.

Aside from the obvious, what made the moment even more difficult was its sudden nature. During playoff baseball, commercial breaks are brief respites from the crushing stress of the moment to moment of the games themselves. You are usually able to ramp back up gradually as the inning progresses. Not this time. Boone led off the bottom of the 11th and launched the first pitch he saw into the stands. In fact, as I remember, the broadcast I watched cut back from commercial with Tim Wakefield already beginning his windup.

Thankfully the 2004 season played out the way it did or else this might be an even worse memory than it already is.

Keaton DeRocher

There’s been a lot of happy moments lately for the Red Sox fans, so what’s better than during a time like today going back to the sad times. It just seem fitting. I’m guessing this will be a repeat moment but the first time I cried about the Red Sox was, of course, Aaron Boone’s homer in 2003. I remember watching the last innings with my dad and as soon as Boone hit the homer, my dad just got up and went to his bedroom, offering nothing to console me but a hearty, “get used to it”. Thankfully I did not need to. Even though it was one moment, and so many Red Sox fans they had to endure more than one moment, it was some misery with which I was able to bond over with past Red Sox generations, which is kind of nice. But for now, on to the next one.

Michael Walsh

Being born in 1998, my time as a Red Sox fan has been basically all positive. My earliest memory was the classic ‘04 team, and my latest memory is the 108 win championship team. I must have watched that ‘Faith Rewarded’ 2004 championship DVD 200 times throughout my childhood. So it’s safe to say I’ve been spoiled, at least compared to my dad. However, my most upsetting moment has to be David Ortiz’ final game in Boston. I was convinced the Sox were going to win it all in 2016, and truly believed we were coming back from that 0-2 deficit against the Indians in the ALDS. It was heartbreaking for me to see my favorite player of all time out there holding back tears, especially knowing I would never have a chance to see him play again.

Brady Childs

Three moments jump to the front of my mind.

The first one was 9/28/11. I had just started senior year of high school and was upset enough to take out my composite notebook for English lit and jot down some melodramatic thoughts during class. We were lucky that 2013 came when it did. It washed away a lot of bad memories that could’ve lingered for a long time.

The second was the firing of Dave Dombrowski. This came up on Twitter yesterday when Tim Marchman brought up a piece of horseshoe theory: the beginnings of sabermetric writing and thought is based in arrogance. If you don’t believe me, go and search the old logs. A lot of us, when we get into this hobby, think we know more than the people upstairs and I was no exception. At some point we get smartened up and realize that there’s a lot more nuance to the game than we ever imagined and surrender to the fact that the people upstairs know more than we do. The firing of Dombrowski along with the general direction of baseball has flung me back into thinking that I do know something the guys upstairs don’t know: that the point of the game is to win titles, not to win as many games as cheaply as possible. That doesn’t qualify me to be a member of a major-league front office but it does mean that I understand the point of sport. I mean, the so called “smartest” teams championed the proposal that contracted a number of minor league teams. In what universe is that conducive to winning?

The third thing was the trading of Mookie Betts. Matt has told us not to write about this for months, so I won’t, but you can imagine how I felt about that after reading what I wrote above.

Matt Collins

It was 2011 for me, and I wrote a bunch about that yesterday so I’ll just link to that and move on.

Jake Devereaux

2003 was my nightmare. I was a junior in high school at the peak of my irrational Red Sox fandom. The Red Sox had my favorite player of all-time, Pedro Martínez, on the mound and they were facing a great villain in Roger Clemens. After getting the best of Clemens and invading enemy territory by successfully jumping out to a 4-0 lead they somehow found a way to screw it up. Martínez and another favorite of mine Tim Wakefield would be left on the hook for the loss in a terribly managed game. The Red Sox had no chance at all of ever breaking this curse. The aura of Yankee greatness and the evil magic on Yankee Stadium was real. Aaron Boone was the worst curse that could be uttered to me following this game. I thought long and hard about my future prospects as a fan—specifically the lifetime of pain in store for me as a Red Sox fan. I stayed the course and 2004 happened. To this day I can’t watch highlights from 2004 without crying like a baby. That meant so much more to me than any sport ever should. I keep a picture of that team above my computer and look at it daily. It reminds me that anything is possible and to keep the faith no matter what.