In 2266, Rolano stood by Leroy and other Kuderian Guards when King Wobine faced a winged kurgo in the arena, then he showed the landing party from the USS Enterprise to their quarters. Sylva approached and told him that the emperor had suddenly chosen to marry her. Rolano was arrested and sentenced to death for touching the emperor's fiancee. Kirk pleaded for mercy. Ledoy agreed to consult his advisor Vrunon, but the mysterious wizard agreed with the death sentence. Vrunon agreed to help James T. Kirk, Spock and Montgomery Scott save Rolano's life if they would help uncover his origins. Meanwhile, Kirk took Rolano's place in the arena and fought a dragon-like gordoon. Ledoy later freed Sylva from marrying him, so she could be with Rolano.
- Rolano strikingly resembled newspaper comic strip hero Prince Valiant, a character from medieval England who had been knighted by King Arthur.