Bernie Maddoff  

Skill: conscience of a cold cut

Weakness: cavity searches

Potential game: Grand Theft Everything

He’d be the Wizard at the end of the game who’d been pulling the strings the whole time and somehow convinced his minions they were doing it for charity, like that skit where Mitchell and Webb realize they're the bad guys. His game is like GTA but instead of cars you just walk into people's houses and steal everything. It's a metaphor.