This chapter looks at the twenty letters that Joseph Weiss sent to the author in Cambridge, Massachusetts, over the years 1949 to 1968. These letters offer an insight into Weiss's spiritual constitution and into the extraordinary friendship that developed between him and Professor Gershom Scholem, its vicissitudes notwithstanding. The letters are of value not only for the personal and biographical details they contain, but also because they contribute to a deeper understanding of Weiss's scholarly work, while at the same time enriching one's knowledge of intellectual life in Jerusalem and in the Jewish academic community of the 1950s. Undoubtedly, however, their greatest importance is that they provide a new perspective on Weiss's complex personality and add a unique and personal dimension to his scholarly bequest. Joseph Weiss's letters are unusually frank: they speak of the changing circumstances of his life; his poverty and alienation, particularly during his unsettled period in England in the early 1950s. There are hints of his ambivalence towards Diaspora Jews in England and towards the State of Israel, and one sees his response, wounded and sarcastic, to the criticism of his bold new approach to the study of hasidism.