My Top 10 Worst Moments As a Boston Sports Fan

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I wrote a blog awhile back about my best moments as a Boston sports fan. Obviously, Boston sports has had a pretty good run over the last twenty years or so, punctuated largely by six Patriots Super Bowl wins in 9 Super Bowl appearances during what has been one of the most storied dynasties in sports history. But that does not mean that there have not been painful memories. There was, after all, a time before the recent success when Boston was viewed as a city of lovable losers – with a hockey team that had no Stanley Cup Championships since 1972, a baseball team with no championships since 1918, and a football team that was the laughingstock of the NFL with no championships whatsoever. Even the Celtics – the most storied NBA franchise in history – went through a period in the 90s with some of the worst NBA teams in history. This was in large part after the tragedy of Len Bias, and it took a long time for the team to recover.


So I have been fortunate to have many great memories as a Boston sports fan. But I thought I would compile the list of the worst momemts I have experienced as a Boston sports fan.



  1. Patriots AFC Wild Card Loss to Ravens, January 10, 2010


This one stung because it was a big shocker. The Patriots were right in the middle of their 20 year dynasty run with a home game against the Ravens, one of the few times they had ever had to play on Wild Card weekend. Most pundits expected an easy win, but what we got instead was a 33-14 blowout loss. From the first kickoff, everything went downhill for the Patriots. Even the weird Patriots team of this past season kept it close against Tennessee; that was not the case here.


  1. Patriots Divisional Round Loss to Jets, January 16, 2011


Earlier in the season, the Patriots had blown out the Jets in one of the most humiliating losses in NFL history. By all intents and purposes, people assumed that they would do so again in the playoffs. Even though the Jets have not been terribly competitive for a longtime, there is a lot of bad blood between Patriots and Jets fans. As a Pats fan, you hate to give Jets fans any ammunition whatsoever. This is the one game they will always call your attention to.


  1. The Miami Miracle, December 9, 2018


I remember this one because I was with a group of friends at Professor Thom’s, the Boston sports bar in New York City. The Patriots had the game in hand until the very last play of the game where Miami ran a trick play to win the game. It was and will forever be known as “The Miami Miracle.” The Dolphins – who have been bottom-feeders in the NFL for decades now – are not a team you want to lose to, especially when vying for seeding in a competitive AFC Division. I took a lot of heat after this game from all of my friends. But the last laugh was mine when the Patriots went on to win another Super Bowl.

  1. Celtics lose to Lakers in 7, June 16, 2010


The Celtics had beat the Lakers two years prior fairly convincingly, but this one still stung. There is a window of opportunity in the NBA for teams who are able to build around a group of special players, and that window of opportunity for the “Big Three” of Paul Pierce, Ray Allen, and Kevin Garnett (not to mention Rajon Rondo as a fourth) unfortunately ended in only one NBA title. Of course, their opposition was Kobe Bryant and a cast of All-Stars on the Lakers, but it still hurt to only come away with one title with that group of players.


  1. Red Sox/Yankees ALCS Game 7, October 16, 2003


In 2003, the Red Sox were my favorite Boston team, so I probably never imagined a world where I would not list this in my top 5 of worst moments. The cursed Red Sox had no World Series titles dating back to 1918 and were playing against their most hated rivals in the New York Yankees in Game 7 of the ALCS where the winner received a berth to the World Series. This one came down to extra innings and Aaron F*cking Boone hit a home run off of Tim Wakefield that sent a dagger straight into my heart. Of course, this made 2004’s comeback against the Yankees from down 0-3 in the series and an ultimate World Series Championship all the more sweeter, but I did not know that that would happen at the time.


  1. Bruins/Blackhawks Stanley Cup Game 6, June 24, 2013


This was a great back-and-forth series which had all the makings of a Game 7. The year prior, the Bruins had lost a heartbreaking Game 7 to the Capitals in overtime for an early exit in the playoffs. Of course, they had won the Stanley Cup in 2011 and were looking to make it 2 out of 3 years. I went to this game with a friend. With under 2 minutes to go, the Bruins – who had a 1 goal lead – gave up two goals and lost the game. I went from planning what I would do for Game 7 to watching the Blackhawks carrying the Stanley Cup around the TD Garden ice. Not ideal!



  1. Bruins lose to Flyers in 7, May 14, 2010


Even though this was not the Stanley Cup, this one stung a lot worse than the Blackhawks loss. There is an ebb and flow in sports: the lord giveth with a Red Sox comeback from down 0-3 in a series against the Yankees in 2004, and the lord taketh away by having the Bruins squander a 3-0 series lead and a 3-0 lead in Game 7 to lose 4-3 in the game and the series. Compounding matters here is that I was a student at Princeton, which is a suburb of Philadelphia, and was heckled in the local sports bar as this unfolded. Not to mention that I really hate losing at anything to Philadelphia.


  1. Giants ruin perfect Patriots season, February 3, 2008


This one will be on t-shirts and memes forever. The 18-1 season. One of the best Patriots teams ever assembled loses a tight one to Eli Manning and the Giants to squanded what would have been a 19-0 perfect season.


  1. Bruins/Blues Stanley Cup Game 7, June 12, 2019


Some hockey pundits have ranked some of the worst Stanley Cup champions in history and pegged the 2018-2019 St. Louis Blues as the top (worst) champion in history. And that’s what makes this one sting. The Bruins, on paper, and really throughout the series, showed that they were the far superior team. And yet with a Game 7 on their home ice (a game I attended last year) they came out completely flat and lost. There is nothing as a sports fan I want to see more on my bucket list than seeing the Bruins hoist the Stanley Cup. 2011 happened in Vancouver. That opportunity was taken away from me with one of the most disappointing losses in Boston sports history.


  1. The Boston Marathon Bombing, April 15, 2013


I remember this day because I was not even in Boston when this happened. I was in New York City for work and literally going through the security line when I got the news. I watched helplessly on the airplane TV after I boarded the plane what was going on back home. It was unjustified of course, but I felt like I had betrayed the city in a way by not being there when the marathon bombing happened. My apartment was in Back Bay mere blocks away from the bombing site and I had to show police officers proof of my address to even go home that day. The city was shaken and still is to this day. But seeing the people who ran towards the bombs to help others, the athletes like David Ortiz who rallied the city, and really everyone pulling together was the light at the end of the tunnel for what was otherwise the darkest day in Boston sports history.

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