Theodor Käärik studied law in Moscow and St. Petersburg, but was later known as one of the founders of the Estonian military and the first Estonian state secretary. According to analysis by Estonian War Museum researchers Leho Lõhmus and Toomas Hiio, it was probably painted in the spring of 1915. We can see that Käärik is wearing an ensign’s epaulets, but he was promoted to junior lieutenant on 5 September that year and is unlikely that he would allow himself to be painted as having a lower than his actual rank. However, the St. Anne’s sword that Käärik is holding is an indication that it is the spring of 1915 and not an earlier time, as according to his service record, he was awarded the honour for valour in battles, in which he fought until 1 June 1915. He was then wounded near the village of Shuravkov and evacuated to the rear, but he had received the decoration, the Order of St. Anne for Valour, 4^th Class, in February of that same year and possibly he also received the sword at the same time.

The portrait was painted in Viljandi, where Käärik was probably visiting home. The session produced two paintings of Käärik: the other was by Villem Ormisson, who wrote the date under the painting, which referred to 15 April.

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