Oskar was born in Bossier City, Louisisana. His father was stationed there as a member of the US Air Force. He would move three times before his father finally retired. At the time, the family was stationed at Hanscom Air Force Base in Bedford, Massachusetts. Oskar was 14 at the time and would graduate high school there before he himself enlisted in the military in 2002. Oskar however chose the US Navy and entered the Master At Arms Rating. He served twelve years before getting out in 2014. He returned home to Bedford, MA and joined the Middlesex County Sheriff's Office. He worked there for ten years before moving to Woodcrest.