This article is based on socio-demographic data of 3,352 Estonian volunteers in the Finnish Army during the Second World War. Longitudinal life histories of these men (more than three quarters of them born in 1918–1926) over a period of more than 70 years allow us to analyse the impact of the Soviet regime and repressions on longevity. The war and its aftermath divided this group into four distinct subgroups, creating a situation resembling a natural experiment: 11% were killed during the war, 38% escaped into exile after the war and lived their lives in freedom in Western countries (mainly Sweden, Canada and the USA), 18% were repressed by the Soviet regime, mainly being sentenced to prison or forced labour camps (20% of this subgroup died as a direct result of repressions), and 29% lived in Soviet Estonia. Crucial life history data was missing for only 4% of the total group. Another 4% of the men were still alive, all being over 90 years old. We observe significant differences in the average lifespan across the subgroups. Men who escaped to Western countries lived longest, outliving the group of repressed men on average by 11 years. In addition to the immediate effect, the impact of repressions is manifested in elevated mortality risks of survivors from the latter group over several decades after the end of Stalin’s rule. The results also reveal a general negative impact of the Soviet regime on longevity, reflected in excess mortality among those who lived in Soviet Estonia relative to those who lived in Western countries. The comparison of mortality patterns of these two groups indicates a cumulative effect of risk factors arising from the Soviet regime: excess mortality did not emerge immediately after the war, but rather in the later stages of life (after the age of 60).