Nadja and Laszlo have known Simon for centuries; he travelled to New York on the same ship as them and during so he had a romantic relationship with Nadja. She and Laszlo settled on Staten Island while Simon went to Manhattan. He became king of the Manhattan vampires there at the age on 107 and owned a vampire nightclub called the Sassy Cat Club. The Staten Island vampires would frequent the club during the 1920s. Prior to the documentary filming, the flatmates had not seen Simon since 1976.
After being tasked by Baron Afanas to take over the new world, the flatmates plotted to join forces with Simon. They came to the Sassy Cat Club and Simon happily caught up with Nadja. When her roommates caught up, they proposed their plan to him. Simon agreed to join them, but only if Laszlo handed over his witch skin hat, despite Laszlo’s reluctance and Nadja’s insistence that the hat was cursed. Simon’s crew, the Leather Skins, intimidated Laszlo into handing it over, but Simon went back on his deal, kicking them out of the nightclub. As they left, Simon accidentally blew up the club while trying to fire a flaming arrow, thus becoming the latest victim of the cursed hat.
With his nightclub ruined and his health badly deteriorated, Simon began lurking in the sewers of Staten Island, secretly plotting to get the hat back. One night, he lured a passing Laszlo and Nadja into the sewers by calling out to them. He claimed that Carol, a strange vampire he befriended in the sewers, and Count Rapula were the only remaining members of the Leather Skins, the others having abandoned him. Nadja felt so sorry for him that she offhandedly invited him to their house, leading Laszlo to storm off with her. The two argued on the way home and upon arriving, they found Simon, Carol and Rapula already receiving a house tour from Nandor. Laszlo immediately suspected that Simon was only there to gain the witch skin hat back.
During his stay, Simon gifted the residents a sculpture of a bat he made from trash found in the sewers as a token of gratitude for letting him stay. Unbeknownst to Simon, Guillermo accidentally killed Carol trying to defend himself from her. Simon secretly recruited Elvis Presley, now a vampire renting a coffin in the house, into the Leather Skins.
Simon recovered to his normal self and called a ‘house meeting’. He announces that he assumed Carol ran away and demanded to have the hat back. Laszlo retrieved the hat and he and Simon fought over it, with both parties repeatedly stealing the hat back and getting injured due to the hat’s curse. The fight moved outside and Simon led Laszlo into the sewers in bat form. Laszlo’s roommates followed them and became outnumbered by the Leather Skins, with Simon wearing the hat. Nadja demanded to know why he wanted the hat so badly, Simon asserted that he was envious of Laszlo and Nadja’s relationship and could not gain satisfaction from anyone, including his own gang. Simon then realised his foot had become stuck on the sewer grating he was standing on, which started to break, leaving him to slowly sink into the water below. The Leather Skins, offended by his lack of caring, refused to help him and Nandor, Laszlo, Nadja and Guillermo left. Simon’s fate is unknown.