Rudolf Mäesepp was a fellow student of Konrad Mägi at Stieglitz Art School, and studied there at the same time as Mägi, from 1905 to 1907. Unlike Mägi, he did not leave the school as a protest over the crackdown on the 1905 revolutionaries nor did he travel to Åland Islands or Paris. They saw each other again only when Mägi returned to Estonia. Mäesepp, later a merchant, also worked as an artist, but he never became a significant one.

At the time of the portrait, Mäesepp was in his late 20s. His attire and bearing give a certain sense that he might be a dandy, which is not surprising as Mäesepp was not only a successful businessman but the son of a wealthy book dealer and real estate owner; he stood out at Stieglitz for his easy come, easy go attitude to money. His nickname was Croesus and another fellow student, Gustav Mootse, says Mäesepp didn’t put that much value on money. “He was the baby of a rich family,” writes Mootse. “And as a baby of the family, he lived like a total gentleman in comparison to us, because his family was generous when it came to their youngest son and brother.”

Konrad Mägi painted portraits of men on several occasions, but unlike women, he gave them all a singular psychology and instead of idealizing, he personalized them. The men he depicted come from different social classes: besides the successful businessman (Mäesepp), he also depicted cultural Others (a portrait of an anonymous Romani man, and Jewish men, Natan Altmann and Bronislav Orlovski), an avant-gardist (Altmann), a conservative (Friedrich Kuhlbars) and senior state official (Theodor Käärik). Thus, Mägi does not construct any particular social class, ethnicity or even an idea of male identity in his male portraits, as the pictures are personalized and the models come from different backgrounds in age, social strata and nationality. Decorative details also have less prominence in the male portraits. For example, the Mäesepp portrait has an evenly green background and the clothing is not ornate (although it is stylish). Kuhlbars is characterized by shelves full of books (there is nothing like that in the background of any of the female portraits). Thus, Mägi helps the male models rise to the fore; they are not decorative objects that melt in with the background.

The reproduction of these works without the express written consent of the owner of the works is prohibited.