Jack Bass

Chuck's uncle who comes to New York upon hearing of his brother, Bart Bass' death, and slept with Blair on New Year's. Jack headed Bass Industries in Australia and served as Chuck's legal guardian when Bart died. He then plots to take Bass Industries from Chuck and sets him up by having the Board of Bass Industries to witness his debauchery and inebriation. Chuck turns to Lily to remove Jack from Bass Industries due to his incompetence at handling the assets of Bass Industries causes the business to become stagnant. Jack loses hold of Bass Industries when Lily decides to become Chuck's new legal guardian, thereby transferring a significantly large power of the company to her. Jack then confronts Lily while he is high and attempts to rape her until Chuck has him kicked out of the opera. Jack is then sent back to Sydney. By the third season, during Chuck's opening of his new hotel, Blair aids him in getting a liquor license for Chuck by contacting Jack. Chuck confronts Blair for contacting Jack and Blair receives flowers and a note stating that the liquor license is fake. Blair and Chuck eventually allow the police to end the opening party and therefore receive enough press and publicity for future clients for a genuine speakeasy that Chuck has been planning.