Montgomery was a smart child and the previous owner of the Super Mario Koopa Capers adventure book the club bought. While playing through the book, the club found that Montgomery had already solved a puzzle in the book. Murph called him a "privileged little brat". It was theorised that Montgomery was very intelligent (a Mensa baby) as he hadn't solved any of the other puzzles the club ran into, meaning he had avoided all their missteps.
It was later revealed that Montgomery was actually host Caldwell Tanner.