When he was a child, his brother drowned. He tried to tell his parents, but they didn't listen, so his brother drowned, and he spent the rest of his life blaming them for this. When he grew up, all he wanted to do was help children, that is why he got a job at Pluckies. He applied for manager, but was turned down.
Now an employee at Plucky Pennywhistle's Magical Menagerie in Wichita, Kansas, Howard is using a Hoodoo spell to exact revenge on people he perceives as mean or neglectful parents. Howard takes a drawing of the child's fear, which the restaurant chain encourages them to do on placemats, and combined with an object owned by the parent. There is power in the child's fear, and combined with the spell, it manifests in reality.
When Sam and Dean arrive in town, one man has been killed by a gaint octopus, and then another is gored by a unicorn. When the janitor Saul offers to give Sam information, he is killed by shark in the kiddie's ball pit.
Another employee Cliff tells Dean and Sam he and Saul heard noises coming from the sub-basement. When one of the waitresses Libby berates her son Tyler, she appears to be the next victim. Sam follows, on the lookout for the giant robot with laser beam eyes (Tyler's fear).
Dean goes to the sub basement, and finds Howard's hoodoo books and equipment, including a cauldron with a fire in it. Howarde confront's him, and tells him he's put a spell on Sam. As Sam watched Libby and Tyler, he is approached by two evil-looking clowns, who attack him.
Dean manages to get a clown statue Howard owns, along with a drawing he did of his brother drowning, and tosses them into the fire. Howard's drowned brother appears, and Howard "drowns" and with his death his magic was undone, and Sam survived.
- Magic - Using fear based magic, he could manipulate the power of people's fears, and limitly warp reality, and make the fears become real to kill people.