I think you need to go back and rewatch that episode . Damon was not at all sure he would be brought back when he crashed his car . It was the entire reason he was so dead set against Elena being in the car with him ! Remember ? Elena jumped in at the last minute and he vehemently tried to make her get out . Therefore , imo , if he was sure . why would he care if Elena was with him ? Wouldn ' t he be just as sure she would come back as well ? Furthermore , Damon is a fatalist . He sees things that happen to him as if they are meant to befated to be because of his past actions . I believe he has always assumed he is going to hell . That is why he constantly says he is a bad guy . Why he has said to Elena over and over . I ' m not good for you . He believes he deserves the bad things that happen to him . That is why I believe going to hell would not scare Damon . In season 7 he hallucinated that he had burned Elena up and even had to watch his brother go up in flames as well ! He tortured himself with those visions for much of season 7 but survived . Now , if what Sybil showed Damon as hell is a vision of Damon having to endure an eternity of scenes like that torturing , maiming and killing Elena andor Stefan then yes , it would be absolute torture to Damon ! It is his worst possible nightmare . losing the two people he loves most in the world , moreover , being personally responsible for their deaths . again and again . and again . I would agree that visions like those would definitely make Damon want to run as far and as fast as he could . He ' d flip every switch he had to avoid such a gruesome ending . However , since TVD writers have not cared enough to actually show us what Damon is seeing . I cannot actually say his hell is watching himself torturing or even killing Elena andor Stefan . However , from the way they talk about it . I don ' t think that is what it is about . Imo , it appears more as if it is Damon himself in hell and that is what is scaring him . and after watching this show for so many years . I just don ' t think that would terrify Damon , because , in his true fatalist fashion , that is what Damon thinks he honestly deserves . Damon doesn ' t wear rosecolored glasses . he ' s a fatalist and a realist . he knows he ' s done bad things . unless hell included killing his brother andor Elena , I just don ' t see him panicking . But then again . since Damon is the writers ' proverbial whipping boy , this plot may have no point at all . It might simply be just another way for TVD to rehash and regurgitate the good old storyline of Damon needs to be saved again drama . They have to do it at least once a season before they move on . this might just be that moment .