The territory was therefore heavily militarized and added to the Soviet Baltic Military District which included a strong presence of the Soviet Air Defence, Navy and also the Strategic Rocket Forces.
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As a consequence to the German occupation of Estonia during World War II (1941–1944) and fleeing the Soviet occupation of Estonia (1944), Ole left as a refugee to Finland in 1943, where he continued to paint portraits of personalities of Finnish cultural life, such as the ones of the linguist Lauri Kettunen and of Viljo Tarkiainen, biographer of Aleksis Kivi, and landscapes.