Oskar Rodriguez was born on October 3, 1986 in San Juan, Puerto Rico. His parents, Dr. Oscar Antonio Rodriguez and Wanda L. Ramos, raised him and his older brothers Oscar Antonio and Oscar Alberto in a warm and loving environment. Oskar and his siblings attended school at the American Military Academy in Guaynabo, where Oskar was taught under the Military pedagogy the importance of responsibility, dedication, organization, and integrity.