James Loeb (1867–1933), one of the great patrons and philanthropists of his time, left many enduring legacies both to America, where he was born and educated, and to his ancestral Germany, where he spent the second half of his life. Organized in celebration of the sesquicentenary of his birth, the James Loeb Biennial Conferences were convened to commemorate his achievements in four areas: the Loeb Classical Library (2017), collection and connoisseurship (2019), and after pandemic postponement, psychology and medicine (2023), and music (2025). The subject of the second conference was Loeb’s deep and multifaceted engagement with the material culture of the ancient world as a scholar, connoisseur, collector, and curator. The volume’s contributors range broadly over the manifold connections and contexts, both personal and institutional, of Loeb’s archaeological interests, and consider these in light of the long history of collection and connoisseurship from antiquity to the present. Their essays also reflect on the contemporary significance of Loeb’s work, as the collections he shaped continue to be curated and studied in today’s rapidly evolving environment for the arts.