Does anyone else feel bad for Winter?

Sure, he is objectively a villain and a terrible person, but he has also spent some unknown amount of time on Duskmourne. At that point, doing whatever you need to in order to escape is perfectly justified. Everyone else on the plane is going to die there anyway. The only truly unjustified act of evil he did was being cruel to Loot. The fact that he almost managed to escape Valgavoth, twice, but then had it ripped away from him at the last moment by meddling plansewalkers is so annoying. Come on writers, just give the poor dude a break.

On the bright side, this likely means his part of the story isn't over. Unless Valgavoth brutally murdered him, but I doubt he did.