The correspondence between two great men – Ivar Ivask (1927–1992) and Bernard Kangro (1910–1994) – from the first half of 1959 is the focus of this article. Ivask was a scholar of literature, the editor-in-chief of the periodical Books Abroad/World Literature Today, an organiser of the international literary scene, a critic, a poet and an artist. Kangro, on the other hand, was one of the most important Estonian émigré writers, the editor of the periodical Tulimuld, and the managing director of the Eesti Kirjanike Kooperatiiv [Estonian Writers’ Cooperative]. The correspondence between Ivask and Kangro began in March of 1951 and Ivask was its initiator. He wrote to Kangro to advise him on the content of the new periodical Tulimuld. Thereafter Kangro proposed that Ivask write an article for Tulimuld on the comparison, translation and criticism of Estonian poetry. Ivask’s first article in Estonian ‘Contemplations on the Tasks of Criticism of Estonian Literature’ was published in 1951. The most interesting period in their correspondence turned out to be the end of the 1950s, when Ivask came up with the idea to put together a collection of selected poems by Kangro to mark Kangro’s 50th birthday in order to identify the best of Kangro’s poetry and to embed it in the literary canon. The motivation for this was apparently Ivask’s dissatisfaction with the anthology of Estonian poetry compiled by Arvo Mäe (vol. I in 1958 and vol. II in 1959). The correspondence between Ivask and Kangro is a valuable document concerning the views of each of these men on literature.