The problem is that you let it get to five. FIVE?!?!
Wow.
The first time, if he's polite, he gets his rope and uses it up. If you didn't feel the need to tell him we aren't going to discuss judgement calls at the end of that, then a QUICK stop sign at the BEGINNING of the 2nd time out gets him that speech. Not the 3rd... not the 4th.... not the 5th.
Too much rope. FAR too much.
And after you said what you said, and he started up... toss him.