I remember discussing this when I first came to the boards along time ago. Back then I was pretty emphatic that Hendo would KO Rich rather easily.
I still think Dan would be the favorite and probably win. His duck my head and throw right hands routine would only have to catch Rich once, and it seems pretty fair to say that he could take Rich down if he gets in serious trouble on the feet. However, I really don't like Hendo at 185. He loses something at that weight. He hasn't looked good there in awhile.
So if Rich doesn't get caught with Hendo trying to brawl, I think he could eventually overwhelm him as the fight progresses.Although I don't think he could finish him.
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