Of course you can win any hypothetical fight if you pick completely stupid moves for the other guy. I mean, if we're going to be that ridiculous about it, my warrior with crappy gear and most skills around 80% is going to take out your assassin with the damage from a single bash because the assassin is so f'ing dumb he's standing visible at Market Square Galadon convulsing and a tick from starvation death.

I would argue that a warrior, even with mediocre skills, who lets an assassin get away with what you describe in your post would have to be much worse than the poor bastard who just slips up and runs out of food at a bad time.