Dragiša after high school,  studied law, but because of his anti-communist and anti-regime belief, was expelled from the university. In Ljubljana subsequently managed to continue studying law. Meanwhile writes books for children and published his first two titles "Tales from the Zoo" and "Nasreddin." In 1952, the District Court in Dubrovnik sentenced Dragiša, as a student of the Law Faculty,  eight months in prison for attempting to illegally leave Yugoslavia. Kašiković managed to cross the border of Yugoslavia in 1955 and seize to Austria, where he stayed for two years. After a hard struggle for survival, with seven dollars in his pocket, he came to the United States. As written by the diaspora chronicles, he went over there to "fight against communism in the homeland and strengthens the Serbian spirit in exile with ancestral faith and human care." Upon arrival in Chicago he became editor of the emigrant newspaper "Freedom," a voice of  Serbian National Defense, which was about to close, but  Kašiković, quickly brings the reputation back, creating rich content and a active newspaper. In 1963 Kašiković runs a literary newspaper "Today" and the satirical newspaper "Velcro" and successfully runs radio program by Serbian National Defense. Translates  thousands of pages of text for Orthodox Church in America from English into Serbian, and all major institutions of the Serbian emigration rely on Dragiša's education, patriotism, enthusiasm and organizational skills. Dragiša Kašiković  graduated from college and perfectly mastered English, German and French in the US. Kašiković was 45 years old when he was killed in the night between 18th and 19th June 1977.