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Rupert of Rathskeller.

Former aide to the late Prince Basil of Caronia.

When Caronia's King Charles travels to Washington to secure a loan from the United States to keep the army of Caronia strong, rotten ruthless Rupert of Rathskeller follows, determined to stop the loan, take over the army and kill the king [Episode #106: "To Sire, With Love, Part 1"].

To this end, he kidnaps Charles from the Smarts' apartment where he has been staying and holds him hostage for the Royal Diamond Scepter which the king has brought with him as security for the loan. Maxwell Smart, after discovering a secret hideout below the Caronian embassy, engages Rupert in a duel, saving the King's life, but Rupert escapes, quoting Kipling as he goes, "He who retreats from battle today, lives to continue the war tomorrow" [Episode #107: "To Sire, With Love, Part 2"].

Portrayed by James Caan (credited as "Himself").