Since you decided to behave I'll respond to this thread now.
Kimbo winning is a pretty big long shot IMHO, but weirder things have happened. If he wins, then yes he would have to get a pretty good camp together and really work on the ground game while becoming an actual striker and not a brawler.
To be honest, I just think the days of the brawler are almost over. MMA is at a much higher level now than it was maybe even 2 years ago. We're starting to see much more well-rounded fighters who can't just beat you in one facet, but in all facets. The quality of fighters on TUF for season 10 in terms of athletes is sounding pretty incredible as well. So yeah, long shot.