I swear to god if he says, "Ah jeez two more weeks again, sorry guys." I'm going to have an aneurysm.
What a fucking asshole. There's no way, simply based on the timing of the deadline and "woops" posts, that he isn't just procrastinating over and over again, realizing he can't make it at the last minute, then giving himself as much breathing room as he possibly needs to destress before doing the same shit the night before again.
This man is his own worst enemy, and if he had any self awareness he'd hold himself more accountable instead of less. Otherwise, he'll never get any better.