IF THEY KNEW CAS WAS INFAMOUS FOR BEING A LITTLE SHIT AND FUCKING STUFF UP FOR THE ANGELS AND PICKING HUMANITY
WHY WOULD THEY SEND HIM IN AFTER DEAN IN HELL I MEAN HONESTLY???
“OH YEAH LET’S JUST SEND THE DUDE IN THAT REBELS EVERY TIME LET’S DO IT GUYS”
OR MAYBE HE WASN’T SUPPOSED TO AND WHEN HE ANNOUNCED HE SAVED DEAN EVERYONE WAS LIKE
“OH DAMMIT NOT THIS AGAIN”
Or he wasn’t supposed to come back at all. Maybe they sent him to Hell, hoping he wouldn’t return, because they knew Castiel would put his everything into saving the Righteous Man.