Leonard usually hangs around at Ted E. Bear's Mafia Free Playland and Casino, where he has managed to amass 10 million tokens by cheating at Indian Poker when the Freelance Police encounter him. After they cheat him out of his 10 million, he steals the casino's famed Meatball Sandwich. Sam and Max capture him when they find him trying to sell the sandwich to Jimmy Two-Teeth and torture him with Your Mamma Jokes.