Why shouldn't he? No reason for anyone to get wound up here. Let it go.
Back to the OP: If we assume a straight 1/3 chance to win any game, given that someone wins one game, there is a 1-in-81 chance they'll win five.
Given that someone has won five games, there's a 1-in-729 chance they'll win eleven.
Therefore, since there have been fewer than 729 five-time champions, I'm not all that surprised that we haven't seen it.
(Yes, I know that a five-time champion is more than 1/3 to win any given game. However, if we assume that there are roughly 10 five-game winners per season, then there would have been 80 of them since Ken's run, roughly. To get a 1-in-80 chance that a five-game winner will win six more, the probability of a five-game winner to beat two random opponents would have be roughly .4817.)