Gary is the thoughtful, by-the-book president of the Midnight Society. His stories often involve magic which usually causes trouble, either by its nature or after someone unleashes or tampers with it. He gets most of his inspiration from the items from his dad's magic shop, Sometimes he brings them to the stories or acts as though he'll work magic. A recurring character from his stories is Sardo, the owner of the Magic Mansion magic shop, after David gave the character a second appearance in The Tale of the Dark Dragon for Gary's birthday (his first in The Tale of the Super Specs ended with him trapped in a crystal).He is Tucker's older brother and is often driven crazy by him, though they share some moments of closeness; Tucker was later inspired to start his own Midnight Society and give Sardo a few more stories. When he meets Sam, he develops a crush on her which Tucker and later Stig love to tease him for, though his shyness makes it take him a long time to learn that she has one on him back. He is good friends with Frank, considering him to be one of the best storytellers since he told The Tale of Cutter's Treasure along with him, and Betty Ann, confiding in her about Sam.While he is in college, he receives a message from his grandma Aggie to take on a task by his grandpa Gene, who has just died. He visits Tucker's Midnight Society and starts to tell them The Tale of the Silver Sight , about a cursed charm, then reveals it's real. They go to find and destroy the Silver Sight. After he, Tucker, Megan, Quinn, Vange, and Andy find all the pieces in the puzzle and locate it hidden in a carousel horse, he is forced to choose whether to trust the mysterious waif kid claiming its power can be used against those who oppose them, and the antiheroic General Liang Candle who claims the kid is a demon and the Silver Sight ultimately leads to the user's destruction. Since one of the clues leading to it was to know the true enemy, he turns the Silver Sight on the kid identifying it's him. It works, and the demon is destroyed. Before he leaves, Gary sees Gene's ghost riding the carousel, smiling in thanks to him.