This monograph uses the life and work of groundbreaking female classicist Wilmer Cave Wright to examine several questions about the rise of women in that discipline. First, what went into the creation of a classics scholar under circumstances that would seem to preclude that? Second, why was it arguably Wright’s time in Chicago that was her formative experience and period? Third, why did Wright want so desperately to leave Bryn Mawr, and then stay and pour herself into her students? Fourth, through what lens did she approach the evidence of classical literature, and did it make a difference? Fifth, how did Wright survive the Thomas years at Bryn Mawr? Sixth, why did she abruptly abandon her long-term project on Libanius of Antioch? Seventh, what led her to suddenly switch from classical Greek literature to translating medieval Latin medical texts? Wright’s journey from Mason College to Girton College, Cambridge, the University of Chicago, and Bryn Mawr College is placed into historical context. Throughout, the significance of Wright’s work, particularly on the life of the Emperor Julian, is assessed.