@Lock We can hazard a guess : Maybe Jyi is the reason why the girl that was with Skoll is dead (But I mean, in the past, when he was a "full" star with omnipotent power). Skoll said it: "I can't forgive you! Forgiveness is impossible!". That means that Jyi is the cause of something related to Skoll.
Since Jyi had no memories of it when he contracted with Skoll, this one waited for Jyi to recover his memories and make him face all this shit. Like, Skoll wanted to know if the current Jyi would go on a path that is "correct", meaning protecting people and such, after recovering his memories.
But I guess we'll only find the answer in the third part of the trilogy.