Smiling Hugh O'Connell was an Irish-American crime boss who lived in the Five Points of Manhattan, New York City during the 1860s. In 1864, Carwyn Rodrick approached O'Connell for help with stealing the proceeds of a Union Army benefit gala; O'Connell was promised 50% of the score and even more money if he killed NYPD detective Kevin Corcoran. However, when the money box turned out to be empty, O'Connell accused Rodrick of hoodwinking him and stabbed him dead; Robert Morehouse had stashed the money in his wooden leg.