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Walter Benjamin's sonnets, written to mourn his friend Fritz Heinle, constitute an important though little-known part of the philosopher's literary achievement and a unique contribution to the history of the German sonnet. Benjamin would add to their number over a decade, having begun his project soon after the outbreak of World War I and the suicide of his friend. They were among the writings that Benjamin, forced to flee France, entrusted to Georges Bataille in 1940 for safekeeping. Here, for the first time, readers of English are offered translations of all 73 Heinle sonnets along with the original German text and an extensive commentary. The Introductory Essay examines the poems' biographical context as well as Benjamin's bold approach to sonnet writing. These poems weave the deeply personal together with Benjamin's evolving religious and philosophical perspective--shedding new light on the emergence of the man and the thinker.