Dragoslav was born in Belgrade to a family of well connected politicians. But shortly following his birth, Dragoslav's father began to rapidly descend withing the Serbian political structure, threatening the family's prosperity. Desperate and afraid of the alternatives, his father made a deal with the influential Serbian Mob, agreeing to become their lobbying puppet in exchange for power and status. Dragoslav grew up alongside his older brother Dejan, and they were raised among an unhealthy mix of organized crime and high class society. Dejan began working with the mob as soon as he entered high school, becoming an accountant and finance manager, an underrated but highly valued skill in their trade. A few years later, as Dragoslav finally entered adolescence himself, the young man wanted to follow his brother into a life of organized crime, having gown up idolizing the mob as heroes. His father could do little to stop them both from pursuing such a life, and Dragoslav was taken in by Dejan's crew.
He was taught to shoot and to smooth talk, both being necessary skills to survive in their line of work. Dragoslav would often help to provide security for his brother when on important business, or when they were expecting retaliation from some rival gang. It was a dangerous and hectic lifestyle, but Dragoslav was well suited for it. Unfortunately for the Novak family, their father soon fell out of favor with both the mob and the government, and everything they had built together soon came crashing down around them. Their father was assassinated in the study of their family home, and the brothers knew they would be targets themselves. There was no time to mourn or to retaliate, and they made the decision to flee to the chaotic and recovering nation of Chernarus, hoping they'd be able to avoid anyone sent after them.