Fedor/Werdum was the most instantly soul crushing for me.
Fedor/Werdum didn't really affect too much after the fact. Has a sort of changing of the guard feel to it. The Bigfoot fight, on the other hand...
Fedor/Werdum was a big deal to me. Werdum was a pretty sizeable underdog, he wasn't seen as much of a threat at the time. A lot of people dismissed it because it was such a quick loss. His Werdum loss took him right off the P4P rankings on here. The Bigfoot fight wasn't as shocking for me. He lost his aura of invincibility with the Werdum loss imo.
He did lose a lot of that aura after the Werdum loss, but the BF fight showcased how far he'd really declined, both physically and tactically IMO. Fedor fought a who's-who of the hw division for a decade, but none had even come close to putting the beating on him that Antonio Silva did. So in my mind, the Werdum fight shattered his aura of invincibility, the BF fight showed us just how far he'd fallen, and the Hendo fight was kind of like the funeral of his mystique.
Funny story about that fight........I'm trying to watch this event but my GF has been a bitch all day and we are fighting/yelling so I'm missing all of the fights. Right about the start of this fight she finally stops bitching and we get to the fun make up sex part. During which I hear "OHHHH" "OH MY GOD" come from the TV so I push her off and dart naked into the living room to see what the fuck just happened. Now I'm jumping around completely ecstatic that Crocop went down, but boy she didn't see it that way.
Fedor vs Bigfoot. Watching HW king getting pounded was depressing.
Silva vs Wedman. Many people nearly quit mma watching that here in sherdog.
JDS vs Cain ll, lll. Disgusting to see a man taking punishment that long period of time.