In the decades around the turn of the 20th century, American business leaders took their first sustained interest in higher education. This historical article, based on archival analysis, challenges the traditional understanding of these wealthy individuals' philanthropy as either passive or ill-intentioned. Using Andrew Carnegie as a case study, the article shows the evolution of one very visible industrialist from a critic of American higher education who oriented his philanthropy elsewhere to one of its most ardent supporters. In between those extremes, Carnegie became a reformer who administered his largesse strategically and helped to bring American colleges and universities into closer connection with the interests and ethos of the business world. His evolving project ultimately bolstered the legitimacy and stability of both sectors.