Oscar Whitehead is a smuggler. According to Verbal Kint, Oscar was picked up at the John F. Kennedy International Airport by Officer Steve Rizzi and Sergeant Jim Strausz, two corrupt police officers of the New York Police Department, where they are a part of a high profit racket known as New York's Finest Taxi Service consisting of numerous corrupt cops driving smugglers and drug dealers all over New York City for a few 100 dollars. Jim and Steve were driving Oscar to Staten Island but were robbed by five criminals, Verbal, Keaton, McManus, Fenster, and Hockney than set the police cruiser on fire. Though, Jim, Steve, along with fifty cops were arrested, Oscar got prohibition.
He later became a target of the Anti-Hunters.