Most heartbreaking loss EVER for the city of Boston?

[LB3533]

For me it's Game 7 of the 2003 ALCS.

They weren't supposed to lose that game, not like that.

[JSD]

This is the first championship series I've ever seen Boston lose and it hurt the most.

[Celtics18]

I agree with many of you.  '86 Red Sox was hands down the most devastating loss. 

I was 17 at the team, and not really a big baseball fan. I'm still not big into the sport, but, yeah, there was something just nasty and wicked about the way the Sox lost that one.  The hurt was personal and deeply wounding for all New England sports fans.

[butterbeanlove]

Bill Russell would be proud of getting booed by the crowd of jackasses in LA. And then he'd let out that trademark cackle.

Most devastating loss? Probably 1987.

[Pucaccia]

Mine was Bucky "F@@king" Dent

[Surferdad]

Bill Russell would be proud of getting booed by the crowd of jackasses in LA. And then he'd let out that trademark cackle.

Most devastating loss? Probably 1987.

Yeah 1987 was awful, but we knew that McHale's ankle and Bird's back were in bad shape.  I think Parish was hurting too.  Just like this 2010 Celtics team, you can argue that they over-achieved based on the injury situation.  Therefore, I consider neither of them the most heartbreaking loss.

[looseball]

For me it's Game 7 of the 2003 ALCS.

They weren't supposed to lose that game, not like that.

Maybe Doc had a Grady Little moment when he eschewed his bench in game seven.

[greg_kite]

I wasn't around for it but I'm guessing trading Babe Ruth wasn't a great day for Boston fans.

I didn't witness the 86 series but that seems to be the worst actual loss in a game.

I was personally devastated when Reggie died.  Just an awful day.

The loss to the Lakers sucked but given the overall circumstances (4ht seed, beating the Cavs and Magic) the season overall was a success.  The Lakers were favorites and had homecourt.

The Pedro/Grady Little game 7 was rough too.

[boscel33]

By far, Bill Buckner for me. 

I was coming off such a high of the C's in 86, then was devastated by the Len Bias death that the Sox had captured me in the fall, only to be crushed by a "slow roller up the first base line".  I hear that call in my sleep, still.  How could Mcnamara leave Buckner in.  It's why teams carry defensive specialists, to substitute when the game is on the line!

[Eja117]

I just can't let this thread go.

Here's my question about all these other things. Did you cry after 18-1? Honestly I thought it was exilerating. It was instant legend that took almost two miracle plays within a play. Humbling in the best possible way. Even Bostonians could appreciate the David vs Goliathness, which we ourselves had against the Rams.

Did you cry after this loss to the Lakers? I didn't. The team totally exceeded expectations.

Did you cry after the Bruins? There were key injuries. It was epic.

But grown men still cry many years later after Buckner, and will for many years more. It was probably one of the only truly traumatic thing I feel like I saw in sports. It was maybe the eqivalent of Barabaro in the horse world for people that REALLY like horses.
I cry for myself, but even more for him.  And then for the city to treat him the way it did and then years later to have a big banner saying we forgive him?  The guy was hobbling out there and he was trashed for two decades and nobody ever apologized. Even though I was only a young kid I will always be embarrased and not really ever forgive myself about the things I said about Buckner. That play had more to do with us than the play.  I'm not sure, but I suspect the only player that suffered more abuse in baseball was Jackie Robinson, but he knew what was coming and is a great triumph of history.