My 10 Saddest Baseball Moments

As a baseball fan of over 35 years, I’ve experienced thrilling victories and heartbreaking losses that still linger in my memory. Of the saddest experiences I’ve had as a fan of baseball for over 35 years. Perhaps you’ve got your own saddest moments. If so, these might pale in comparison to yours, but to me, these stick out.

From enduring gut-wrenching playoff defeats with my favorite teams to getting lost in an unfamiliar neighborhood outside of a stadium, here are ten of the most poignant moments from my journey as a baseball fan:

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1. Player Too Busy For Autograph

I was 16 or 17. One of my favorite memories growing up as a baseball fan is watching legendary players come out of Yankee Stadium after a game. This happened for the first time in 1985. The clubhouse exit was next to the parking lot, and through the years I got to see some of baseball’s greatest players. On this one day, I hadn’t actually attended the game but instead was watching it on TV. I left my home, knowing it was likely that the game would be over by then and I could wait for my favorite players to come out. I got to see a lot of players exiting the clubhouse. One in particular, unfortunately, didn’t have enough time to give me an autograph as he was in a rush. The player wasn’t rude. It was clear from his quick pace that he was genuinely in a rush, not trying to brush me off or anything like that. I felt a bit disappointed that I couldn’t get an autograph, and at that age, perhaps I hadn’t been as forgiving a person because I was young. But still a sad moment.

2. Getting Lost Outside of the Stadium

In September 1993, I got to visit my first baseball stadium outside of New York City. The name of the place was Joe Robbie Stadium, former home of the Florida Marlins. On that day, they were playing the Los Angeles Dodgers. I decided to go to that game solo. I got to see many of my favorite players from both teams, including former Mets who were now on the Dodgers team. After the game, I stood outside the stadium where I’d been told players might come out, and to my amazement and surprise, I got to see quite a few players. I stayed until Ramón Martínez, the phenomenal pitcher for the Florida Marlins and brother of Pedro Martínez, a Hall of Famer who also played for the Mets years later. After the game, I wandered off outside the stadium and ended up lost. I honestly think to this day that I was lucky. I approached someone working on his car outside his home and asked if he could take me to the nearest gas station. At first, he was reluctant but then took me there. From there, the owner of the gas station drove me straight to my university.

3. Injuring Myself Just Before Little League All-Star Game

In the summer of 1988, I was chosen by my teammates and manager to play in our Little League All-Star game. I was thrilled, as this was the second time in three years that I’d been picked to participate in the event. Sadly, during one game I injured myself, rupturing my hamstring on the run to first base. It is, to this day, one of the most painful injuries I’ve experienced. Right after the game, I was informed that I’d been selected to the All-Star team, which only made me feel worse. I was told that it would take place a week later—nowhere near enough time for the injury to fully heal. I sat out most of that crucial game, only stepping in as a pinch hitter late in the innings, where I managed to draw a walk. The pain was still there, but I decided to take the risk. Fortunately, I didn’t have to run, which could have aggravated the injury. The combination of the injury and being unable to fully participate in the All-Star game makes it one of the saddest baseball moments of my life.

4. Mets Loss to Dodgers in 1988 NLCS

The 1988 World Series loss to the Dodgers is one of my most painful baseball memories. I can still vividly recall Howard Johnson making the final out by striking out. Then I see him looking down before heading to the bench. Two things make it particularly sad for me. The first is that the series went seven games, so they were close to making it to the Fall Classic, yet were outperformed by the Dodgers. The second is that this occurred in a visiting stadium, so the raucousness of the crowd as the team clinched the win was painful. They say that silence is painful, but I personally would have preferred them to lose at Shea. The memory of their loss still haunts me.

5. My Favorite Broadcaster’s Death

I was saddened by the death of iconic broadcaster Tim McCarver’s a two years ago. McCarver was one of the greatest broadcasters ever to call games. His analysis and interesting tales while broadcasting, as well as his expertise, brought something special. He paired well with Ralph Kiner, who sadly also passed away. Kiner was older than McCarver. His death too was painful, but somehow, I thought to myself, he’d lived a very long life. McCarver seemed to have a youthfulness within him as well, and I miss him. McCarver also responded through his assistant when I wrote one of my first ever emails, in 1998. I believe I’d asked him a question about his favorite wine, and to my pleasant surprise, I received a reply. He will be dearly missed by me and all the Mets fans who found his broadcasting both entertaining and informative.

6. The Cubs’ Loss in the 2003 NLCS

This was painful for every Cubs fan. The team had been in the playoffs since 1998. Prior to that, it had been 1989, but they hadn’t reached the World Series since 1908. Watching this game, like every fan, I thought the Cubs would at least hold on, that the team would finally make it. And the beauty of it would be that they’d meet the Yankees in the World Series. Both teams are storied franchises, and it would be just as thrilling for me to watch them play against each other as it was when the Mets met their cross-town rivals. But, alas, the 8th inning was tragic as the Marlins came back, seemingly out of nowhere, to take the game and eventually win the National League pennant.

7. My Last Game at Childhood Park

March 1995 was the last time I ever played baseball, as far as putting on a uniform and playing on a field. This park, located in the Bronx, is where I’d often spend weekend summer days watching my uncle play. It is because of him that I have a love of baseball—back in the 1980s, he introduced me to the Mets, one of the dominant teams of the decade. On my very first at-bat, I got hit. It wasn’t painful. In fact, it didn’t hurt at all. I proceeded to first base, and then, a batter later, ended up on third. The inning ended moments later, and little did I know that it would be the last time I ever played a game. It was also around the time of the MLB strike, so we fans faced the possibility of not seeing baseball that year, which added to the air of sadness surrounding this whole event of me playing for the last time.

8. Darryl Strawberry’s Leaving the Mets

Darryl Strawberry leaving the New York Mets for the Los Angeles Dodgers was and still is one of the saddest moments for me. But the sadness would eventually disappear, as several years later he ended up back in New York City with the Yankees. Even though I’m not as great a fan of the Yankees as I am of the Mets, he helped propel the crosstown rivals to greatness during the 1990s, taking them from a team that wasn’t so great to one that would win four World Series titles in five years.

9. 1994 Strike

I still can’t shake the memory of the 1994 strike. That year must have been particularly sad for Montreal Expos fans, as the team, at the time of the strike, was in first place and had its most serious chance of making the playoffs since the 1981 season. This strike is especially sad for me because it happened right in the middle of summer, when baseball seems to be at its height. We wouldn’t see baseball again with regular players until April of the next year, so essentially we were all left nine months without baseball. A sad time I will never forget.

10. Ricky Henderson’s Death

Like every baseball fan, I was saddened by the death of Rickey Henderson. He was an inspiration to me, and I can still remember the first time I went to see a live game at Yankee Stadium—coincidentally on my 10th birthday (the community center in our neighborhood sometimes gave out free tickets to kids who cherished baseball, and that happened to be one of those lucky days). I was actually working on an article that mentioned Rickey Henderson—I included him as one of the best players of all time. When you saw Rickey Henderson play, you admired all of his skills and ability. I also liked his swing and how he would make that jerky move after catching a ball. I could not believe when he passed away. At 65, he still had a lot of life ahead of him. Without a doubt, he is one of the greatest to have ever played the game. There will never be another Rickey Henderson. I will always remember him for the excitement and joy he brought to me as a fan of the sport. He may no longer be with us, but he will always live in the hearts of baseball fans.