The article reconstructs the main periods and facts in the biography of the Ukrainian intellectual Mykhailo Drai‑Khmara in the historical and cultural context of the 1910s–1930s, focusing on his poetic, critical, translation‑related, and linguistic achievements. Drai‑Khmara’s poetic activity is analyzed from the perspective of the transformation of his individual style, which went through the stages of symbolism, neoclassicism, and socialist realism. In the field of literary history, Drai‑Khmara specialized in Slavic studies, especially Croatian, Polish, Belarusian, and Ukrainian literature of the 18th–20th centuries. The scholar made a major contribution to the development of national comparative studies by analyzing works of the Ukrainian writers in the context of European literatures. The posthumous promotion and reception of his heritage in the United States of America and Europe are also described. This article provides special information on Drai‑Khmara’s connections to Romania, including his travel in 1913, the poem “Constanța” dedicated to it, and also the reception of his work in Romania.