The answer is literally NEVER! He says it near the beginning; he thinks that everyone around him is literally playing to the drama scenario that he made up randomly to Alpha long ago. He does not even for one second think any of it is real! XD To him they are all actors who are helping as supporting characters to make his whole Shadow Lord Act as cool and edgy as possible. One BIG part of this problem is that - for better or worse - because he never says anything about plans or the situation happening around them, all of the other characters think he's freaking brilliant and that everything is under control and that all is going according to his plan! XD This unfortunately only helps to further feed in to the supporting cast scenario with their absolute trust in him to take care of everything so no one ever thinks calls him out on his bullshit because of how well everything turns out. XD