[The Red Eminence]

I really like this question.

I can't predict the future, but I'll say no for now. I think it depends on how this season goes. If Kiffin takes this team to the expanded playoff, then I say he stays at Ole Miss. In this scenario, why would Kiffin leave a team with playoff potential for a program that needs significant rebuilding. By rebuild, I don't just mean in the team's structure, but the culture as well. I see your point that Florida has the means to be great in the future. It absolutely does, but it won't have the immediate success that Kiffin might enjoy at Ole Miss. 

Also, if Kiffin goes to Florida there will be an intense pressure to succeed. Frankly, he just doesn't have that at Ole Miss. If he produces many seasons with a high win count, then he should be safe. I think at some point Kiffin leaves Ole Miss for a bigger program, just not now.