I think Penn was plenty big for a LW. I think his cardio and his mental state were the biggest detriments. I think his refusal to adopt any type of game planning till MMA had caught up--and passed him--was critical as well.
What if Fedor had adopted a regimen that had leaned him out to within reach of LHW? [Let's just go ahead and assume that in this alternate universe you're suggesting, the Fink took the path he was truly destined to perform and produced lo-quality Russian porn with mail-order bride-wanna-be's]
What if Anderson wasn't hobbled by soares, and made enough money where he literally gave not a single fuck, and felt comfortable enough to challenge himself against whoever, whenever, wherever?
All manner of men came to work for the News: everything from wild young Turks who wanted to rip the world in half and start all over again -- to tired, beer-bellied old hacks who wanted nothing more than to live out their days in peace before a bunch of lunatics ripped the world in half.
Dr. Hunter S. Thompson
The Rum Diary