Winston is a traumatized kid who dislikes getting a fairy godparent because of what Jorgen did to him. Due to being traumatized, it is shown that Winston develops post-traumatic stress disorder, due being terrified by Jorgen, suffering from the torture of his babysitter, Alyssa, making his life very miserable. Despite this, Winston is fully aware of the existence of fairy godparents and their godkids. This is either because the fairy council forgot to erase Winston's memory of Jorgen and his days as a godchild or the fairy council taking sympathy for Winston towards Jorgen's treatment of him decided to not erase his memory as long as doesn't reveal the existence of fairies. Much like Cosmo freaking out if someone mentions the Super Toilet and Astronov getting angry if someone mentions Juandissimo's name, Winston can get terrified if someone mentions Jorgen's name, which causes him to hallucinate about Jorgen and faint.
He has red hair and wears a red and yellow striped shirt.