Not sure if anyone’s has similar thoughts, but I felt that every time he dies in the dungeon the people close to him dies instead of him. Kinda like in exchange for allowing him to red pawn the dungeon takes the lives of his loved ones. So once he has nothing left to take from, then he won’t be able to despair anymore...
If anyone had spoilers from the WN tag me. I’m quite interested to see if I’m right.