I want to say kid yamamoto. But injuries played a big part so even though it's somewhat understandable it's hard watching him lose now when you think of how dominant he used to be. 
Huerta. Dude had a great roll in the UFC, one win away from a title shot...
Leaves, goes to smaller promotions and has a terrible ride. I don't even know when he's fighting anymore, just log on here each day and then I see him getting his head kicked off.
Also, he's still quite young so that's even more surprising. 
Tyson,is a good one.......he was widely regarded as a future multi,time champion ir contender and he really got lost in the shuffle.......
Jens
Bob sapp
Hardy
Dave terell
Heath 
Joe daddy. Never been the same since he was destroyed by bj 
Filho and Kang surprised me. They each have had a lot to deal with - chemical dependency and the loss of a loved one, respectively.
Bones Jones once he goes to heavyweight
Rick Story... Honestly thought I was looking at the answer to GSP and the next champ a few fights ago. 
Vemola.
Was throat slashing at opponents and shit beating them till he came to the UFC and hasn't really been at all as effective since and dropped 2 weight classes.
GSP24 - People are naming former UFC champions for fucksakes. Do you not know what a career fail is? It sure as shit ain't a former UFC HW champ who defended the title twice.
Fucking stupid fack!
I win by saying David Terrell.
/thread. Goodnight. 
People are naming former champions because he asked about the biggest career fall, not fail.
Chuck.
I said Rampage would beat him again, but I did not think his career would go downhill so rapidly.
The shocking thing about Fedor's loss is that it was to a grappler! If he lost via getting KO, due to his sloppy punching style, would make perfect sense.