Oh Brotha.
Fedor shouldn't be compared to Kimbo in any sense.
As a BJJ practicioner, and a member of the Relson Gracie association, I will say that Rickson, in all his greatness, would get destroyed by Fedor. If Mas Funaki, can clip Rickson, Fedor would pummel him. Big Nog, who is the best MMA fighting BJJ blackbelt got destroyed by Fedor on two occasions. Fedor's ground and pound would KO Rickson from Top. Rickson is only superior on the mat, without striking. I don't think his closed guard would be sufficient to stop Fedor from posturing up and dropping some heavy strikes to KO Rickson.
Regarding the loss to Tripp, "he didn't understand the rules." 
If they were to fight again, Rickson by armbar. (had to say it.)
You are delusional, and I mean that with no disrespect. Rickson's record in professional fights is 460-0. Show me a single fighter that can even approximate this. If we include amateur brawls, that record rises to 2,000+ wins with no losses.
You seem to ignore that, even to this day, most fights end on the ground, and who's the king there?

Are you really that insane that you believe that Fedor would be able to grapple with Rickson once they are on the ground? Fedor has a small chance of knocking him out when they are still standing, but that's his
only chance.
If you think that Fedor's greater size and strengh would close the deal, think again. Rickson has fought with Zulu, a giant who outweighted him by 100 lbs, and who could crack the trunk of a small palm tree with his base hands. Strikers, graplers, wrestlers; Rickson has fought with all and defeated them all. Boxers, kung Fu masters, black belt karate champions; all were demolished by Rickson. As for a BJJ black belt having been defeated at MMA, who cares? He was not Rickson.

Rickson makes black belts seem like white belts. Like Royce said:"Rickson is ten times better than me. When it comes to him, I am just a fan like everybody else." Or to quote Mirko Filopovic:"Rickson is Zeus, the god of the gods." Just accept the facts that Rickson is the greatest ever, and bow down before crushing greatness when it's staring at you.
