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What are your most emotionally devestating moments as a fan?

Being biased towards my boys Hunto and Jamie Te Huna it's their losses that hit the hardest, but probably James more than Hunto, since James has taken the harder falls.

The Stipe loss was hardest to take of Hunto's, especially because I was pissed at him for not taking his prep seriously. For James it was the loss to Marquardt in Auckland, because I was there and because I knew how much it meant to him.

Anderson's leg snapping was also pretty harsh.
 
Anderson Silva breaking his leg v Weidman. Watching him scream like that was
Difficult and I didn't want him to go out that way.
This would have fucked me up a little more, but I went into the fight thinking he would get knocked out, and then when he broke his leg it took a little while to even understand what was happening. If I would have seen his leg rubberizing in real time it probably would have made me ill.
 
Really felt for Condit after the Lawler fight. To put that much into it and not get the verdict. Robbery would be harsh but I thought it was a close but clear victory for Condit.
 
Gus getting ko'd in his hometown in front of thousands fans..that was hard to watch, also after the fight interview..

The last time i cried was, when they execute john coffey in the green mile.
 
Really felt for Condit after the Lawler fight. To put that much into it and not get the verdict. Robbery would be harsh but I thought it was a close but clear victory for Condit.
I thought it was karma biting him in the ass for what happened in the Diaz fight =)
 
When Reem gets knocked out by a fighter he's expected to beat
 
Watching Junior taking so much punishment in the last 2 Cain fights.
 
Cro Cop / Gonzaga by far.

Pretty much every Ken Shamrock fight from Fujita onwards.
 
For some reason, I felt really bad watching Rockhold crush Machida's skull with elbows. I'm not even a big Machida fan. I still felt a kind of pure sorrow when I watched it.
 
1) Gus giving his all and coming up just short against Jones
2) Watching Gus getting "Rumbled" live in Stockholm and seeing how gutted/tearful he was after
3) Gus giving his all and coming up just short against DC

4) reading post on sherdog about how Gus has no heart!!!
 
Gus losing to Jones. Not that is was a robbery.. could've gone either way.. but a big Gus fan.
 
As a Barao nuthugger, the TJ fights were heartbreaking for me. The 2nd fight in particular was bad because I saw it with my girlfriend at the time and was in a really crappy mood after the main event. Ended up yelling at her over some stupid shit in front of my friends. Not my proudest moment.
 
Chuck just chuck man poor guy, really thought he was unknockoutable but damn. The way he just walked through that guy metzger head kick, I just thought every fight in his prime he would just eventually knock everyone out at some point in the fight. Then he fell so hard so fast it was awful.
Rampage4Real. Lol
 
Maia getting KTFO by Marquardt hurt me more than any other fight
 
Shogun losing to Jones, for sure.

When Mirko got KO'ed by Gonzaga... I was traumatized, but I just like, IDK, at that point in my life I couldn't really process what happened, when Shogun lost to Jones I was a little bit older and in touch with my emotions and that fight really scarred me

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and that was also like the beginning of MMA not really being that good for me as a fan until just this past year or two.
 
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Gus beaten down by Rumble infront of his people
Fedor's 3 fight skid
Shogun vs Jones
 
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