Most heartbreaking loss EVER for the city of Boston?

[Eja117]

Here's a few for me.

Losing Tim Duncan

Losing Greg Oden (at the time) AND Kevin Durant

Losing Bird's healthy back

Losing Ray Bourque cause there was just no way on Earth to get the guy a Stanley Cup

Losing Adam Vinitaeri to the Colts

When the British occupied the city during the Revolutionary War. Not as bad as Buckner, but still

I was very frustrated when BC was ranked as high as #2, lost to VA Tech in the ACC championship game and was given something like the Champs Sports Bowl. Then something very similar happened the next year

Watching the Bears in Super Bowl XX grab the Pats' arms, punch them with them and say "stop punching yourself. Stop punching yourself"

Losing Doug Flutie to graduation, then Canada, then retirement

Losing DJ

Losing with Rick Pitino on a nightly basis, and then losing your marbles when walking into a book store and seeing "Success is a choice"

Losing justice when our senator was given time served or some such thing for drowning a girl

Losing his brothers to assassins

Harvard losing a squeaker to Yale for the national championship in 1894....just kidding. Made that one up. But I bet you something like that happened

[nickagneta]

As a child it was losing Bobby Orr to the Blackhawks. I was too young to understand the intracacies of the contracts and agents and management. All I knew is the biggest hero in Boston sports history(sorry CBers he was bigger than Bird, Orr OWNED this town) was going elsewhere and 35+ years later, I'm still just a very very casual Bruins fan. At the time, I knew little else but Bruins hockey.

[celticsclay]

Here's a few for me.

Losing Tim Duncan

Losing Greg Oden (at the time) AND Kevin Durant

Losing Bird's healthy back

Losing Ray Bourque cause there was just no way on Earth to get the guy a Stanley Cup

Losing Adam Vinitaeri to the Colts

When the British occupied the city during the Revolutionary War. Not as bad as Buckner, but still

I was very frustrated when BC was ranked as high as #2, lost to VA Tech in the ACC championship game and was given something like the Champs Sports Bowl. Then something very similar happened the next year

Watching the Bears in Super Bowl XX grab the Pats' arms, punch them with them and say "stop punching yourself. Stop punching yourself"

Losing Doug Flutie to graduation, then Canada, then retirement

Losing DJ

Losing with Rick Pitino on a nightly basis, and then losing your marbles when walking into a book store and seeing "Success is a choice"

Losing justice when our senator was given time served or some such thing for drowning a girl

Losing his brothers to assassins

Harvard losing a squeaker to Yale for the national championship in 1894....just kidding. Made that one up. But I bet you something like that happened

I can see most of yours, but vinateri? He is not even the worst patriot loss in the past 10 years. If we were to pick one with a lot more meaning it would have to be losing curtis martin to the jets. That definetely set back our running game a long time and helped our rivals!

[guava_wrench]

I'm a Mets fan, but Buckner seems like the answer to me due to their long drought. The Celts did win 2 years ago. I thought the Magic hook was far worse than this year since we so overperformed in the playoffs this year and it was also clear that we ran out of gas in the game.

[PosImpos]

This loss can't be considered that heartbreaking because of the level of expectation surrounding it compared to the other examples.

18-1 was so devastating because the Patriots were clearly a much better team (the best in the league by far) and they just had a really bad game at the worst time possible.

The 2010 Celtics were never really meant to get as far as they did, considering all their regular season issues, their 4th seed, their age, etc.  They overcame all kinds of odds, and fell just short of winning it all.  That's not really a heartbreaker.

Also, in both the aforementioned cases, the team had won a championship recently.  Buckner probably stands out above any of the others because it perpetuated the Red Sox curse.  You can't really be heartbroken as a fan if your team has won in the last couple of years.

[Q_FBE]

Wow, a bunch of tough choices there. I went with other only because I go back a bit further than you guys. I picked the 1971 1st round of the Stanley Cup Playoffs when #8 Montreal beat #1 Boston with a rookie goalie named Ken Dryden. Then there was that too many men on the ice with 2 minutes left in game 7 in 1979 and Boston leading 2-1. Montreal gets the tying goal and wins in OT.

18-1 was bitterly disappointing considering the distractions of Spygate and the Hatriot Culture. I wanted to win for the FU value. That also was the turning point in Boston sports karma and for me personnally.

[Kuberski33]

The Buckner game was by far the worst.  2nd is the Bucky Dent Game in '78.  3rd for me Game 7 Bruins/Canadians -- the Too Many Men on the Ice game -- final game of the Don Cherry era, which made it all the sadder.  After that is Game 7 of the '75 World Series (Jim Burton has become obscure, but he killed a dream season when the Sox came out of nowhere).

This one is probably 5th.  But it's definitely in the ballpark with the other four.

[nickagneta]

I gotta believe the younger crowd is pushing the Game 7 loss to the Lakers to the front of this poll because anyone that can remember the 1971 Stanley Cup or the 1986 World Series or the 1978 one game Yankees-Red Sox playoff game or even the SuperBowl XX(heartbraking on a grand scale because of the never before seen in this area hype of the SuperBowl and also for the absolute record setting, at the time drubbing the team took) game knows this last game just doesn't compare. Heck this isn't even the most devastating loss in Celtics history, the baby sky hook game in 1987 was the worst.

[bstnsportsfan3]

my first true heartbreak from boston sports was the 2003 alcs...i was born in 1987 and my dad taught me of the horror's of being a sox's fan (Dent, Buckner, ect....)so i was a 16 year old kid who started dancing when the sox's went up 5-2...and  then grady left pedro in, timmy wakes knuckler didnt knuck...and we all know how that turned out my dad looked at me 3 seconds after the ball landed in the stands and told me my red sox virginity had just been broken and i knew what it was like to be a sox's fan....i just stood their staring at the screen, then felt a deep pit in my stomach...i got up, screamed " i dont wanna be a F@#$#%$ red sox fan anymore"...and went to bed...never gave up my fan hood but i was devastated until next season made up for it....lol looking at it know i realize  how bad a reaction that was but i loved the sox's and hated to see it end like that....to me it was the worst moment i have had as a boston fan....close second is 18-1....this celtics game? no where on the radar...we were playing with house money at this point and it was a hell or a season.

[Bahku]

"Loss" being a subjective word, and assuming this is in reference to sports, for me it would have to be the death of Len Bias.

[celticsclay]

im still pretty upset and its been quite a few days. I guess i could answer this question better a few months from now

[Eja117]

I gotta believe the younger crowd is pushing the Game 7 loss to the Lakers to the front of this poll because anyone that can remember the 1971 Stanley Cup or the 1986 World Series or the 1978 one game Yankees-Red Sox playoff game or even the SuperBowl XX(heartbraking on a grand scale because of the never before seen in this area hype of the SuperBowl and also for the absolute record setting, at the time drubbing the team took) game knows this last game just doesn't compare. Heck this isn't even the most devastating loss in Celtics history, the baby sky hook game in 1987 was the worst.

I think I agree with you nick that it must be young guys pushing the results. I don't think anyone will get physically bad reactions to watching replays of this 20 years later like Buckner.

[Roy Hobbs]

I think that without a doubt it has to be the 1986 World Series.  There was so much riding on that game, after 70 years of negative history.  To blow the game like they did was the ultimate stomach punch.

That said, the Game 7 loss against the Lakers sucks, and has left me with a deflated feeling ever since.

[Kuberski33]

The common denominator with the games I mentioned is just being stunned over the result.  I actually forgot to include the Pats/Giants Super Bowl.  Definitely had the feeling then too.

I think those 6 games get grouped together.  The Magic sky hook game is a notch below -- not that it didn't royally suck, because it did.

But the Buckner game stands alone...especially because it was the Mets with all that obnoxious hugging and the various clowns that squad had between Dykstra, Strawberry, Garry 'Lights' Carter, Hernandez and all those other jerks...

Part of assessing level of losing is how much you hate the other team...... 

[Mr October]

Pats/Giants by far. Even though I am much more of a Celtic fan.

The Pats were supposed to win that game.

The Celtics weren't supposed to even be in the finals this year. It was a great run.