Despite Joseph Brodsky's apparent dislike of the Russian turn-of-the-century classic, in 1993 he wrote a poem titled in English: “Homage to Chekhov.” The poem, which stylizes the atmosphere of some of Chekhov's works has since puzzled several Brodsky scholars. The central question of the scholarly debate has been whether Brodsky sought to pay the playwright a belated homage or was instead deliberately mocking Chekhov in a parody. This article takes another stab at the mystery adopting a new approach: it looks for the solution in the poem itself, rather than in the history of Brodsky's dislike of Chekhov or in his polemics with literary critics. My article identifies a number of Chekhovian subtexts in the poem and explains how exactly Brodsky achieves the effect of a Chekhov pastiche here. It also draws a connection between “Homage to Chekhov” and some of Brodsky's poems dedicated to the theme of fin de siècle. The article puts forth a hypothesis: Brodsky did not think he would live to see the millennium and this brought him closer to Chekhov, who did not live to witness the start of WWI – the “actual” beginning of the 20th century. I argue that by 1993 Brodsky had reached the age when he could better appreciate Chekhov's lack of resolve. I show that the figure of Erlich in the poem is a stand-in for Brodsky himself. That Brodsky depicted himself behind the mask of a Chekhovian character seems to indicate that around the end of his life the notoriously unpredictable poet might have experienced a change of heart about Chekhov.