Letters of the poet Mikhail Isakovsky to the literary historian Anatoly Abramov (1917–2005) published in this article constitute a portion of the poet’s extensive epistolary legacy. The two selected letters dated 1968 are mainly concerned with the poet Aleksey Prasolov (1930–1972), whose literary career Abramov actively supported. Having approached Isakovsky for an opinion about the Voronezh-based poet’s verses, Abramov received very harsh feedback. There can be a number of reasons why the poems, some later recognised as Prasolov’s best, were dismissed by Isakovsky: the fact that the two poets belonged to very different poetic generations and traditions and adhered to disparate aesthetic principles may have played a key role here. A poet of a traditional folk-poetic formation, Isakovsky rejected Prasolov’s verses, whose poetics is directly influenced by Blok’s modernist experimentations. Isakovsky expected Prasolov, an author of challenging complexity, to write about subjects easily recognisable and clear to the reader. Thus, incompatible ideas about a poet’s purpose and dissimilarity of poetic languages precluded the two remarkable poets from ever meeting in person.