The Top 10 Worst Boston Sports Moments In My Lifetime

A.B. As if Mondays aren’t already bad enough, it seems I can’t go anywhere on the interwebs today without seeing Eli’s ugly mug with the Lombardi Trophy.

The whole world is rejoicing in our pain.

However I have always found the winning to be so much more enjoyable when I surround myself with the agony of defeat. I watch Buckner miss the grounder whenever it is shown. I never look away when FOX shows Aaron Boone’s home run during every Yanks, Sox game (F-you Joe Buck). Pictures of Kids in Africa wearing 19-0 Patriots t shirts? I try to smile.

African Kid With Pats T Shirt

Patriots T-Shirt Meme











Because let’s face it; ’04 was special because of the 86 years of pain. The Celtics in ’08 was special because it was the first time since Bird.

So excuse me for bringing up our painful past, but misery loves company.

I was born in ’84 so in the last 28 years, here is my list of nightmares come true:


#10) Cam Neely “forced” into retirement: In the end, it was the pain from a chronically arthritic hip that forced Cam to hang up his skates. But try selling that to any Bruins’ fan, and you will get a one-word answer: Ulf. Well, maybe the fan will add a few choice words to describe the player who will always belong on the wall at the Boston Postal Annex with the other nine most wanted criminals. No matter what anyone says, Boston blames Ulf Samuelsson and his knee-to-knee check during the 1990-91 Eastern Conference Finals for Neely’s premature retirement. Case closed.

#9) Damon signs with the Yankees

Damon was not the best player on the Red Sox when they broke the 86 year old curse. But he may have been the most important. Whether you look at his 2 big home runs in game 7 of the the ALCS, his ability to get on base & steal bases or simply his role in the group of “idiots” who changed Red Sox culture forever; without Damon… ’04 wouldn’t have happened.

So when he jumped ship in the off season to sign with the HATED Yankees, Boston was dealt a blow that we would never forget… or FORGIVE.

#8) Brady tears ACL & MCL

It was time to avenge the 2007 perfect season loss. The Pats opened the season at home against the lowly Chiefs. It would be the first win in another perfect season… or so we hoped. I’ll never forget this day.

I went into the kitchen to make a Sunday morning mimosa. My girlfriend was napping on the couch. 5 minutes later I walked back in the living room ready to catch a buzz and enjoy some football.

Brady is down. He’s holding his knee. He never returns.

2008 is a wash. Cassel plays well but the Patriots without Brady just isn’t the same.

#7) Travis Roy paralyzed

I was young when this happened but already playing & watching hockey every chance I got. Hockey was my life. I even had a t-shirt that said so.

So for a naive 11 year old to watch a lifeless player laying on the ice at BU’s Walter Brown arena, it was very scary.

I remember it was the first time I realized how human college & professional athletes were. No longer were my heroes immortal.

#6) 2010 Celtics Game 7

This was a choke job plain and simple. Up 13 points in the 3rd quarter. About 6 minutes from another Banner. The Celtics finally looked old. If you can’t finish, you won’t win. That simple.

#5) 2010 Bruins Game 7

I was at this game. I wish I never went.

My buddy who manages The Greatest Bar called me after the 2nd period and said he had 4 tickets unclaimed. The score was already 3-0 Bruins. I grabbed 3 friends and we ran into the Garden to celebrate the imminent victory. On the run over someone yelled, “3-1.” As we got through security, we heard rumblings of “3-2.” Soon it was 3-3 and the rest is history.

That is the first time I ever witnessed a grown main in black & gold face paint yelling to the exiting crowd, “I am going to kill myself!”

No idea if he ever made good on that promise…

#4) ’86 Sox – Bill Buckner Game

I was only 2 when this happened but it still hurts the same. If you are a true Red Sox fan and a Boston homer (like yours truly) this play has been burned into your brain since a very early age. 1 out away. 1 freakin’ out.

#3) ’07 Pats Super Bowl Loss

I’m probably going to get buried for having this as #3 & not #1. But the truth of the matter is that while I thought a perfect season would have been awesome & historic, all I really care about is Championships. And since this was only the first one the Pats had lost since winning 3 in 4 years – the hurt wasn’t as bad (as today).

But don’t get me wrong, this sucked. It was definitely one of the worst days of my life as a Pats fan. Just not as bad as the next 2…

#2) ’03 Sox ALCS Game 7

If I ever see Aaron Boone in person I will punch him in the face. It will result in me getting my a*# kicked & probably arrested, but so be it.

I also extend the sucker punch invitation to everyone at ESPN who had a role in hiring him as an analyst.

If Steve Levy was a real Boston fan he would reach over the anchor desk and knock Boone out.

#1) ’11 Pats Super Bowl Loss

Last night was the worst Boston sports experience of my life.

It wasn’t the perfect season on the line, it wasn’t to snap an 86 year old curse & it won’t keep Brady or Belichick from the hall of fame.

But it was a loss to a New York team, for the second time in 5 years, to a quarterback named Manning – and not the great one either.

There is no chance Brady can ever get the Giants back either. That would take 3 more super bowls, all 3 against the Giants, all three being won by the Pats. Can’t happen, won’t happen.

So for the rest of our lives we have to accept that Eli Manning is 2-0 head to head against Brady in the Super Bowl. Puke.

And what’s worse; we now have to pretend we think that ELI is ELITE. Puke twice.

So without making this an Eli debate, I will say this: He is good in the clutch, he has good fundamentals, he deserves to start on any team. But he is no Montana, Brady, Elway, Marino or (insert name here). He is a talented player who has always had more talent around him.

Can you imagine Brady with Bradshaw, Nicks, Cruz, Burress, Steve Smith, Jacobs, (insert more stars here)?

Instead Brady has won 3 titles with the likes of Kevin Faulk, David Givens, Deion Branch, (insert other role players here).

So lets be smart here. Congrats Eli, you continue to improve. You are good. But you will never be Tom Brady & THE RECORDS & STATS DON”T LIE.

Plus Brady’s still got +1 on you, homie.


Disagree? Plenty of comment space below to give me your edits/order. (Giants fans need not apply)

  • Dan

    Good list. For me, Aaron Boone is a flat out #1 if we’re talking about level of pain at the time. The catch ’07 hurt way more than catch ’11 because ’07 was a fluke play. At least this catch was a skill play, both the throw and the catch.

    Roger Clemens signing with Toronto is missing, that was worse than Damon. Len Bias and Reggie Lewis could also have made the list.

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