Whose fault is it the boy is suffering?
The boy

What should the boy do?
Stop being so damn weak and stupid

What has the boy done wrong/right?
He is weak, believing he can change the world
He did not embrace the world as it is
He allowed himself to be caught up in charms of a woman a second time (fool me once shame on you, fool me twice shame on me)
When the bandit told him to attack a caravan he should have attacked the caravan or the bandit leader, always get the first strike