Bailey began working for the Crosswire family before their second child, Muffy, was born (he was possibly the butler of Chip, their first child). When Muffy was 8, Bailey revealed his hate for his job. After a few physical assaults against the family, Bailey set the Crosswire Mansion on fire (Bailey's Breakdown). It is possible that the entire family perished.
Bailey has a British accent, and he wears a suit and tie. He worked as a butler for the Crosswires, specifically Muffy. In the originial Arthur series, he said that he likes his job. But that was proven to be untrue in Bailey's Breakdown.