In 1913, the young Walter Benjamin struck up an intense friendship with the poet Christoph Friedrich Heinle. As Benjamin’s biographers Howard Eiland and Michael W. Jennings remark, “Benjamin’s relationship with Heinle — which would last for little more than a year — is one of the most enigmatic episodes in Benjamin’s enigmatic life. At once epochal and impenetrable, the encounter with Heinle would leave a deep mark on Benjamin’s intellectual and emotional physiognomy for years to come.” Benjamin was immediately taken with Heinle’s poems and did his best to get them published — unsuccessfully. In 1914, when war broke out, Heinle and his girlfriend killed themselves. Benjamin was deeply shaken, and he began committing his mourning to a sequence of sonnets, at first fifty in number, though eventually there were more than seventy. They were the writer’s main preoccupation for three years, and their style is deeply reflected in his first major literary essay, “Two Poems by Friedrich Hölderlin” (1914-15). Yet the sonnets are little known or discussed — Eiland and Jennings barely mention them — and despite so many decades of insatiable hunger for all things Benjamin in the literary and academic worlds, they were published in translation only last year, in versions by Carl Skoggard, who has already has two other richly commented translations of works by Benjamin to his credit (Berlin Childhood Circa 1900, 2010, and The “Berlin Chronicle” Notices, 2011). Skoggard’s introductory essay is thus an important contribution to Benjamin’s life story. The poems themselves, however, present difficulties that would stymie any translator. Skoggard perhaps puts the best face on it by observing that, “unlike the sonnets written by anyone else,” and “equally remote from dramatic utterance and from sustained lyricism, they strike us as the expression of some hermetic thought process.” The poems’ mashing together of tormented syntax and overwrought emotionalism with strict formality in the handling of the sonnet form (which, wisely, Skoggard has not tried to emulate) has led to results that are often rebarbative, sometimes ridiculous: “But for my lips slow to confess a master / Waited who should better mark them / The hand which hesitates itself to give / / To friend is by him seized a crueler guide / So that the heart which loved in secret / Must now be spilled for all to see in rhymes.” And yet it may be that an understanding of Benjamin cannot avoid passing through these poems. Gershom Scholem, after hearing Benjamin read part of this oeuvre, reflected that Benjamin “can only have a connection with persons to whom he can speak of it” — which was almost no one. “All that he does,” Scholem wrote in his diary, “is intended to raise up, through methodical application, that dark center in which their friendship formed to an absolute brightness.” This brings us back to the enigma that Eiland and Jennings identified in the Benjamin/Heinle relationship. Bearing in mind that “Heinle was, by universal consent, an unusually beautiful young man,” according to Eiland and Jennings, and that “Benjamin could still refer to Heinle and his brother Wolf ten years later as ‘the most beautiful youths I have ever known,’” it’s impossible not to wonder what unspoken sexual component might be harbored in the emotional extremism of Benjamin’s love for his friend, an attachment that, as he later said, let him occupy “a pole opposed to the one that is mine by nature.” What was that nature? The more we know about Benjamin, the harder it becomes to say.