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Squire Winston was a Forever Knight who made his first appearance in the episode The Creature From Beyond. He seems to have a crush on Gwen (much to Kevin's annoyance). He is a squire who was attacked by the Lucubra and turned into a mind-controlled slave. He was seemingly cured when Gwen sent the Lucubra back to its home dimension, but his eyes were later seen glowing the characteristic turquoise of one of the Lucubra's slaves, showing that he is still under its control. Under Diagon's control, Winston joined The Flame Keeper's Circle and became an Esoterica while still working for the Forever Knights behind their backs. He was caught by Ben, Gwen and Kevin in A Knight to Remember and was forced into revealing his secret to the Forever Knights. He was almost beheaded until Ben stopped the execution and saved him. However, he fell under Diagon's control again and not only raided the Flame Keeper's Circle into the hideout of where his heart and Ascalon are kept, but he also tricked Vilgax (who had absorbed the heart while impersonating Diagon) into breaking open The Seal as a ploy to reunite Diagon with his heart and bring him back to full strength. In The Beginning of The End, Winston is seen working for the Forever Knights again. He is now Sir George's squire and aided him during the Forever Knights' battle against the Esoterica. As they approach The Seal, the cult's leader Conduit Edwards sneaks up behind the duo and tries to kill George, but Winston shields him for the blast; killing himself in the process. He was declared to have died a Forever Knight by George instead of a squire.

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