Leonard is a bald overweight man who works 4 hours a days selling toner over the phone so he can devote all his time to playing chess in the park with strangers. He enjoys making fun of everyone who loses to him. Malcolm played Leonard multiple times, but always tied. After seeing Leonard was in debt to rather frightening people, Malcolm gets him a job interview at the Lucky Aide. He is interviewed by Craig, but loses the job after he is seen making fun of him with Malcolm in private. He moved away after this incident leaving Malcolm a letter stating that everyone is a jackass, and that world isn't fit for people like us(Referencing that Malcolm and he are both antisocial).