~narsil has a pretty fantastic collection of icons if anyone there strikes your fancy. but i love this dread pirate roberts'ing idea, and they sound great! i'm still working from some bare bones ideas currently but i think he might have had a somewhat shady magical apprenticeship with a teacher (and now might be a little cursed) before joining up with the guild, so they could at least have some magic ability to bond over? i think he'll be a cavalier thief type but wholly and completely loyal to your leader, and maybe we could come up with some prior backstory that could explain why they work well together or something (or why they'd even hire him as their second-in-command), whatever works best!