Principal Grimley is the principal of Marie Kiddo's school. He owns a "Principal of the Year" mug which he gave to himself, that brings him joy. His computer, which gave him stress, was destroyed by Marie but that only gave him more stress as he wondered what happened to his computer. One of his chairs got thrown through the window as well as a way for Marie to "free him from clutter". He had a change of heart towards Tammy after being asked if she brought joy or not, by saying she is the best student in school. His diplomas were also destroyed after Marie thought they were in pain from being nailed to the wall. His antique mahogany desk was sawed in half with a chainsaw to remove any broken glass bits on it, which resulted in sawdust bits getting in his beard.
At the end, his office was completely destroyed after a truck plowed through the wall of it.