The main character of Sergey Simakov’s painting Saint Cornelius of the Pskov Caves is the hegumen (Father Superior) of the Dormition Pskov-Caves Monastery — one of the most famous, ancient and large monasteries in Russia. Cornelius took the charge of it in 1529 at the age of 28. It was under him that the monastery began to actively develop: the brethren grew to 200 people, there were founded an icon-painting and pottery workshop, a bookish and literary school, the monastery itself was expanded, and there was built a fortress wall. In the end that was what killed Father Superior: according to legend, the fortification angered Ivan the Terrible and he personally killed the hegumen in 1570.

In this painting, Simakov depicted the moment of the assassination of Cornelius in a realistic manner, but the figures of the saints and the monastery buildings are executed in the icon-painting style. Depicting the monastery walls, the artist did not use one-point perspective: the structures are almost proportional in the foreground and background. Simakov combined icon-painting and realistic traditions in his last secular painting — Saints Zosima, Savvaty and Herman of Solovki, 1991.

According to Sergey Simakov, he often painted Orthodox ascetics, admiring their courage, serenity and humility. He wrote that he would like to have their ability to ‘resist attacks and evil and get out of every cataclysm pure, without aggression, without grudge against the evil that was committed against them’.