Upon return to Estonia, some prosperous years followed for the Pitkas. Johan Pitka was one of the leaders of the League of Liberators for a short time but left the organization in 1932. In 1937 he was also a member of the National Constituent Assembly ("Rahvuskogu"). After the Soviet occupation in June 1940, Pitka escaped from Estonia to Finland. In 1941 tragedy struck the Pitka family, their three sons were arrested by the Soviet occupiers and perished. In 1944 Pitka returned to Estonia to organize military resistance to fight for Estonia's independence. Pitka is thought to have died in a 1944 battle.