Fedor's management didn't handpick all his opponents. You think during the GP's they got to choose who he fought next? Back in RINGS tournaments? It's also not unheard of at all for managers to have a big say in what fights an athlete takes. It's part of managing a fighter's career.
In response to your larger question, Fedor's mystique has disappeared to a large degree, but that happens to everyone who doesn't die young. I wouldn't say that his mystique can be reasonably compared to Kimbo's, either. Kimbo's wasn't earned, Fedor's was.
His helmet was stifling, it narrowed his vision. And he must see far. His shield was heavy. It threw him off balance. And his target is far away.