James "Whitey" Bulger $1 million reward

Leader of the Winter Hill Gang, an Irish American crime family based in Boston that controlled illicit drug trade and extortion rackets in South Boston. Bulger has shown how hard it can be to capture a criminal. The FBI has pursued Bulger for more than a decade for Bulger's alleged roles in numerous murders. His wealth is estimated between $30 million and $50 million and he has associated with major criminal enterprises throughout North America and Europe, including the Irish Republican Army. The 78-year-old is using the wealth and contacts he developed through his criminal operations to stay out of the reach of law enforcement and is believed to be on the run with his longtime girlfriend. The FBI has a $1 million price tag on him, but by concealing his appearance and using false identities, Bulger has evaded the substantial effort to bring him to justice. There are indications that he recently traveled to Sicily.