Simon’s practice covers a wide range of civil matters, including commercial disputes, administrative litigation, the defense of class actions, and special remedies such as injunctions. Simon has also acted for shipping interests in various maritime matters and represented clients in the defense of regulatory infractions. Simon is an active part-time Naval Warfare Officer in the Royal Canadian Navy, as well as an avid hockey enthusiast. He played for and managed the McGill University Faculty of Law's unofficial intramural hockey team, and helped organize a charity ball hockey tournament at the Faculty. He also wrote for and edited a hockey stick manufacturer's official blog from 2016 to 2019, publishing technical articles and managing online community relations.