User blog comment:Kajune/SPN's redeemed antagonists/@comment-26992577-20160601113705/@comment-26271908-20160608023402

Like I said: A completely twisted sense of justice. In the Norse Mythology, Loki was known by this. It's not like all his victims did something evil. Gabriel simply thought with his uncommon sense that something they did was evil for whatever reason and decided to punish them in interesting ways. This is what happens when a twisted sense of justice mixes with a murderous sense of humor and a vast array of immense powers

Killing the Archangels everyday would be interesting, but I would love to see them forced to live as Humans without any kind of power and being a prey of a different creature each time to teach them humility. Just imagine it. It would be hilarious

Kajune is right. He thought that killing Dean hundreds of times would break Sam apart and teach him that destiny is unavoidable and he would've been forced to abide it's laws and do nothing about Dean. However, I think it somehow worked: Sam didn't looked for Dean. Surely it was not because Gabriel's cruel lesson but I think it served as the very first step into the concept, like an introdution or prologue