During the events of the novella Dangerous Simon was playing basketball after school was out, three seniors walked up to him and tried to pick a racially motivated fight. Simon "was being a smart ass," and one of the seniors pulled a pocket knife on him. Simon was going to do a knock-back spell, but then Derek came, threw the guy into a wall, and paralyzed him. Derek punched the second one and the third one ran. It got mentioned in the paper, and caused their dad to want to move, because he sensed the Edison Group would be on their trail.
Simon had a basketball game the next day, and Kit did not want Simon to miss it, so he said that they would leave after the game was over. Kit was then taken by the Nast Cabal, upon returning home, Simon and Derek found him missing.
Derek had been unable to find scents of anyone other than Kit. Later Derek and Simon are found looking for their missing father and were sent to Lyle House. After breaking out, they ran to their dad's friend, Andrew Carson, who later betrayed them.
Simon had a crush on Chloe Saunders while on the run and in Lyle House, but after his date (and kiss) with her he realized she was not interested in him. He knew she loved Derek and was okay with them dating, and even drew Derek a picture of Chloe hugging a large black wolf as a present.