Olaf is pretty dumb for hoping he'd die during The Harrowing.
It should have been pretty clear from the sea monster he killed coming back to unlife that dying isn't really dying when it's in The Black Mist.
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Next Year-
Underworld Olaf (Would be a great looking skin)
he did consider that. Locked in an eternal struggle against the Krakenwurm? That is fantastic for him!
He wants to break the "prophecy", it doesn't matters if he becomes undead if he does it with honor.
I think he was too excited to consider that.
It should have been pretty clear from the sea monster he killed coming back to unlife that dying isn't really dying when it's in The Black Mist.
He himself remarked that if he died, he and the ghost Krakenwyrm would "fight for eternity".
It'd be a weird version of Valhalla.
Why would he really care if he's becomes a ghost? He was alive, accomplished many a manly endeavours and even if he becomes a terrifying undead he can still fight monsters as the dead.