Max Gamble

Max Gamble is a money-obsessed stereotypical gangster based out of the Casino Night Zone and running many casinos, as well as various dangerous fly-by-night enterprises. He is so obsessed with money that when Tails was defending the Zone from being exterminated by Commander Brutus, Gamble threatened violence against him unless Tails did it quicker so people would go back to his casinos. He would later try to have Tails killed for humiliating him, as well as loyally helping Robotnik turn people into Badniks.

When Robotnik was overthrown, he made a bid to have his mob assume control over the whole Zone; Tails rallied the citizens against him, and the mobsters themselves turned on him when it was revealed Gamble was sending money to Robotnik. He and his criminal activities would occasionally pop up to harass the Freedom Fighters, including running holidays to Robotnik's old Flickies Island base (which nearly killed several people) before he was finally forced to go on the run. He used the Eternity Ring to escape Mobius and ended up in a world shaped by people's thoughts; he created a world based around gangster films to amuse himself before Amy Rose and Tekno took him down.

In Sonic the Comic Online, he has become a lackey for the Insect Family crime organisation.