User blog comment:IamJakuhoRaikoben/Chapter 402: Iron Fist of the Fire Dragon, Review./@comment-1359322-20140929144423/@comment-25111584-20141001093446

For the reasons you mentioned, I can't really see OS working with Jellal. Brain offered them freedom, but ended up using them. Jellal is offering them the same thing, why should they accept? Once burned, twice shy, right? And I hardly see them following him because they fear his power, they might follow him for a very short time out of sheer shock at their defeat, but they'll recover quite soon. Not to mention the extreme clash in Midnight and Jellal's personalities, think Natsu and Gray with the brotherly love being replaced by childhood hatred. It's far more likely that somebody from OS just backstabs Jellal.

On the other hand, is there something instantaneous that could motivate OS to mend their ways? You know what I'm driving at here, and it's not Hoteye. With Jellal there, he's going to take a while to fulfil that promise, and the OS are hardly going to wait; once they recover, they'll be at his throat again. On the other hand, I can see the group dynamics working beautifully with Jellal out of the picture, serving only as the inspiration for the group. With Brain out of the picture, I think the rest of the OS members now do actually care a lot about each other, what with Cobra's determination to free all but Brain, etc. And, as people who have lost almost everything themselves, they might feel empathy with Meredy, who would have now lost her last partner.

Midnight could easily be a fantastic leader. I'm not referring to the filler arc here, but I like to think of it as foreshadowing this event. Yup, not a great assumption, but a guy can try, right? ;) And I never thought of Meredy as a leader. Hoteye is not assertive ... at all. Meredy could serve as the moral conscience of the group, a role which I find extremely befitting. I ... see no way in which this could work with Jellal unless Mashima just discounts everything and has OS follow him obediently right from the start, which, unfortunately (imo), has a high probability of happening. >.>

Well, as I said earlier, I'm biased about the Erza thing and the romance dynamics of the story in general, so I don't really pay much heed to that, sorry. >.> Though, with 2 extremely hyped bosses still to go, it wouldn't be that difficult for Mashima to set up a situation in which Jellal dies right before OS as well as Erza.

For the last statement, I actually think the opposite. If he doesn't die in this arc, he's most probably going to survive throughout the whole series. There's a good reason for his death now, with him living making for some difficult relationship dynamics to work through. I don't think there will be such a situation later.