Thanks for the reply Insidious,
I usually judge a character by two traits, (1) how much the character offers for personal and overarching plot, and (2) how much fun the personality can be to play. Maybe it's a bit of a throwback from my tabletop experience, but those are often my foci when bringing a character in.
I'll just go over them again in kind.
Sidetrack I can see as a part of a specialist team. I will admit, I have a soft spot for combiners, but understand I can not engage with them (I am guessing there is a reason for this Out Of Character), still, if there is a chance for such a thing to come about as a part of a story arch down the line it could be very interesting indeed. Particularly with his themes of being more together than apart, it can often play to his own ideology.
As for the character, he would be focused around mining and laying foundation, very grounded (pardon the pun), making him akin to a constructicon in allegiance before he turned. I am thinking his specialty being able to quickly loosen earth and splitting rock in a surgical manor.
I think one of the earliest things that needs to be explored with the character is that struggling to integrate with the Autobot mentality, and I can imagine that there are some core Discepticon ideals that he may struggle in letting go, or sometimes twisting an Autobot code with a Discepticon application. It's not that he's completely lost the cause, so much as he's come to realize just how far it will have to go, and in doing so he can't handle the sheer volume of destruction and death that will follow.
Unfortunetly when it comes to playable G1 characters, there isn't one that is really jumping out at me. Still skimming, but haven't found somebot that I feel I am gravitating to. I'll keep looking in case something does show up (Spent the past hour browsing and trying to extend my thoughts on this topic but I am coming up blank).
I understand the risks involved playing such a character as Jailbreak, and if that's the fate in store for him then so be it, it's the character's story to be told. The truth of it is that he's there to serve as a counterpoint, and I imagine without a strong and insightful leader many Discepticons would be at each other's throats more than they already are at times, so it is really on the leader. He's more of force of nature at times, and because of that it may come to situations where it's best to get out of the way and duck for cover, regardless of side. On the other hand, harnessing that behaviour can become a task to show just how good such leaders can be.
I'll look up the OOC chat, see what's up