Skills: Bluff/Sense Motive, Diplomacy, Disguise, Know Local, Know Royalty, Gather Info, Hide/Move Silently, Listen/Spot, Intimidate, Use Magic Device.
Feats: Deceitful, Investigator, Negotiator, Persuasive, Skill focuses, Leadership, Iron Will, Trustworthy, Alluring, Thug?, Streetsmart, Cosmopolitan, Education, Smooth Talk
Rogue special abilities: Skill Mastery, Slippery Mind.
Items: Rign of Mind Shielding or Spell Storing, Rod of Rulership/Rod of Splendor, Staff of Charming or Eyes of Charming, Cloak of Charisma, circlet of persuasion,
Check out Quintessential Rogue I & II for great character concepts and inspiration.
Is he going to be a guild master? Give us some more info to work with...