@Seek_Kolinahr Now you know why I prefer Shadowrun and GURPS; they don’t have artificial constructs like “classes” and “levels” to restrict character design. Makes things simpler :)
Something else to bear in mind is that thieves do all the things they do for the end goal of power. Money is power. Blackmail is power. Assassination is power.
Politics is something that requires Charisma; Bards are a subset of Rogues.
Espionage requires a blend of charm (getting secrets from people) and stealth (getting secrets from their premises). Who are the sweet-talkers and second-story men?
Efficient and stealthy use of deadly force can topple regimes as well as any war can; which of the four class-groups do Assassins belong to?
Taking over a kingdom by force usually means ruling over a barren wasteland in need of rebuilding. Taking over by more subtle means allows you more power, and often a scapegoat that will get killed while you escape.
More importantly, it’s proper role-playing of a Rogue. Rogues don’t do swords, fireballs, or miracles. Leave the hack-and-slash to Fighters, blowing shit up to Wizards, and smiting for Clerics! Rogues are about subtlety, finesse, and getting what they want, preferably without a stand-up fight.
But if he just wants to kill them all then you’re better off just having him play an Orc Barbarian :p