Background/Context: Faculty unionization is an important topic in modern higher education, but the history of the phenomenon has not yet been fully considered. This article brings together issues of professionalization and unionization and provides needed historical background to ongoing unionization efforts and debates. Purpose/Objective/Research Question/Focus of Study: This article examines the context of, debates surrounding, and ultimate failure of the first attempts to organize faculty unions in the late 1910s and early 1920s. Following a discussion of the institutional change of the period and the formation of the American Association of University Professors (AAUP) as an explicitly nonlabor organization, this article considers the founding, endeavors, and demise of 20 American Federation of Teachers (AFT) locals. In doing so, it demonstrates long-standing divisions within the faculty and concerns regarding professional unionization. Research Design: The article uses historical methods and archival evidence to recover and interpret these early debates over the unionization of college faculty. It draws on numerous collections in institutional and organizational archives, as well as contemporaneous newspaper and magazine accounts and the writings of faculty members embroiled in debates over unionization. Discussion: Beginning with the founding of AFT Local 33 at Howard University in November 1918, college and normal school faculty organized 20 separate union locals for a variety of social, economic, and institutional reasons before the end of 1920. Some faculty believed that affiliating with labor would provide them with greater voices in institutional governance and offer the possibility of obtaining higher wages. Others saw in organizing a route to achieving academic freedom and job security. Still others believed that, amidst the difficult postwar years, joining the AFT could foster larger societal and educational change, including providing support for K-12 teachers who were engaged in struggles for status and improved working conditions. Despite these varied possibilities, most faculty did not organize, and many both inside and outside academe expressed incredulity that college and university professors would join the labor movement. In the face of institutional and external pressure, and with many faculty members either apathetic about or opposed to unionization, this first wave of faculty unionization concluded in the early 1920s with the closing of all but one of the campus locals. Conclusions/Recommendations: Unionization in higher education remains contested despite the tremendous growth in organization in recent decades. The modern concerns, as well as the ways that they are overcome, can be traced to the 1910s and 1920s.