There is no specific study about Stephan Kalynovskyi, and the texts written about him contain many mistakes. This article presents the biography of Kalynovskyi, including the following stages of his life: student and professor at the Kyiv Academy, archimandrite of the Zaikonospassky Monastery, rector and professor at the Moscow Academy, archimandrite of the Alexander Nevsky Lavra, member of the Synod, bishop of Pskov, archbishop of Novgorod. In this article, attention is paid to his relations with students and brethren of monasteries, as well as to his intellectual heritage (philosophical course, Bible translation, his library). The sources portray Kalynovskyi as an innovative teacher because he was one of the first at the Kyiv Academy to teach Greek language, history in the course of rhetoric and ethics in the course of philosophy, and also as an organizer of educational institutions. At the same time, he was a very conflict person. His philosophical course, taught at the Kyiv Academy, was copied verbatim from the philosophical course of the French author Franciscus le Rées.