Black Mask
I’ve always had a soft spot for Black Mask and I think of all the characters on this list, the wealthy industrialist deserves his bow most. The son of wealthy parents and notorious narcissists, Roman Sionis is born with a silver spoon rammed halfway down his throat. And despite this, he wants out. He kills his wealthy parents in a fire and pursues a career in crime, slamming those that wear fake masks in public.
In a modern society obsessed with money, there’s an opportunity to skewer consumer culture through the prism of this decidedly frightening mob boss, who turns to a life of crime despite the fortunes showered on him; who seeks to break free of the false masks worn in well-to-do circles.
If you’re anything like me, you’ll be excited to see Black Mask take ownership of the Sionis crypt and begin working towards a life of crime. On another level, his relationship with Deathstroke in Batman: Arkham Origins is proof that these rogues could work together. Mask is the orchestrator, the instigator with money to burn, and Deathstroke is the elite assassin tracking Bats down.