In 1929, he was appointed Prefect of the Greek state of Drama where he held substantial power until 1932. In 1941 he was the active Minister of Justice as part of the Tsouderos government and the Greek government in exile during Nazi occupation from April 21, 1941 - May 2, 1942. Dimitrakakis was then appointed as Temporary Minister of the Army from June 2, 1941 – May 2, 1942 and Minister of Justice and Labour where he remained until April 14, 1944. He was instrumental in orchestrating the Greek brigades that are widely credited with freeing Crete of Nazi occupation during WWII through several operations that originated from the South of Crete and Cairo, Egypt known as the Battle of Crete.