Heavy-Handed Harry is the head guard of the Rock Island Prison, and is involved in the Rocking Out quest. He is so convinced of the security and inescapability of his prison that he knowingly puts prisoners in a cell with a large hole in its back-wall, which allows them to escape regularly.
It is implied during the quest that he suffers from some kind of delusional illness (probably megalomania) and has to be medicated to be kept controlled.