This article examines the citizenship application of Oleg Vassilkovski (1879–1944),
a White Russian émigré and former officer of the Imperial Russian Army who settled in Estonia in 1920. His application was rejected by the Ministry of the Interior in 1935, following a recommendation from the Political Police. As this assessment was apparently based on his long-term activities in Estonia, the article first outlines the circumstances that had drawn the attention of the Estonian authorities to Vassilkovski during the fourteen years preceding his application.

Upon his arrival in Estonia, Vassilkovski established a ship repair workshop in Tallinn. Beneath this entrepreneurial façade, however, he was actively involved in monarchist circles. The organisation he led – the Russian National Union – sought to prepare for the overthrow of the communist regime in Russia, seeking assistance from White émigré organisations operating abroad. In police reports from early 1923, Vassilkovski was described as a fervent monarchist and one of ‘the leaders of the monarchist movement in Estonia,’ who ‘regards Estonia as a future guberniya of an undivided Russia.’

In the spring of 1923, the Estonian authorities decided to expel Vassilkovski, along with several other prominent Russian monarchists, from the country. The decision was justified by his contacts with foreign organisations and individuals acting against the interests of the Estonian state, as well as by his efforts to promote their activities within Estonia, which were regarded as a potential threat to national security. Archival records suggest that despite this decision, the expulsion was never fully implemented due to the absence of legal mechanisms allowing the deportation of stateless persons; by that time, most Russian émigrés had lost their citizenship. Deportation to Soviet Russia was impossible on humanitarian grounds, as it was self-evident what the Soviet authorities would have done to those identified as anti-Soviet, many of whom had also fought directly against the Red Army during the Russian Civil War.

Consequently, Vassilkovski was allowed to remain in Estonia, though he was expelled from the capital, Tallinn, and lived in Pärnu until early 1924. The same pattern was repeated in 1927, when he was convicted of harbouring an unidentified person who had secretly entered Estonia from the Soviet Union – allegedly one of his agents in Soviet Russia. This again resulted in his banishment, first to Hiiumaa and later to Pärnu.

From 1924 onward, Vassilkovski resided in Estonia under a so-called Nansen passport issued to stateless persons. At the end of 1934, he applied for Estonian citizenship; however, the Ministry of the Interior did not support his request. The Political Police advised against granting him citizenship, arguing that his activities had ‘on several occasions been contrary to Estonian interests.’ As the Estonian state did not recognise the former lieutenant general of the Imperial Russian Army as one of its citizens, he remained stateless in Estonia until the Soviet occupation in 1940.

The Soviet authorities, however, regarded him unequivocally as an enemy. After the establishment of Soviet power, Vassilkovski was arrested and sentenced to death in 1941. Although the sentence was soon commuted to ten years of forced labour, he died in a Soviet labour camp in 1944.