This is a character, who’s continual explanations for there own existence, are connected to a classic blunder.
Bus in as many examples, of a thief’s challenge, and you can see, and know for yourself; how impossible. Pass on that one.
The main challenge, is approval of the overall class experience. There are only so many flawless examples, because it is dangerous. The team up, for any skill use, is rare, and powerful compared to other classes. Skills cover up the repeated failures (mostly), but there’s a way into the background with them.
To really get into the design of skill use, the thief is possible for anyone. They may actually gain from being the hanged man, just because there class can’t be ignored. The suave and charismatic, part can include the usual bravado, but the thing about the basic thief level, is that they have skills, and a style. When covering there final story, there escapes and acrobatic movement, show them still in the background unscathed.