The boundaries of higher education organizations (HEOs) are becoming increasingly porous both in the USA and globally. Research has shown that individuals within universities (e.g., trustees and faculty) can serve as boundary spanners who connect universities to their external environments. However, our knowledge of how individuals span HEO boundaries is limited, especially for university leaders. University presidents are leaders that bridge the boundaries of universities via the internal and external aspects of their role. We evaluate the connections presidents establish between universities and external organizations and how they change over time to expand our knowledge of boundary spanners. Drawing on literature on academic capitalism and the interdependencies between organizations, individuals, and environments, we conceptualize how presidents connect their institutions to external organizations and how these connections may differ across institutions over time. Using social networks and latent profile analyses, we examine the connections between elite US universities and external organizations via presidents between 2005 and 2020. Results show growth in connections over time as well as three distinct patterns of connections across institutions. This suggests that presidential connectivity differs across institutions and has changed over time in ways that have implications for university governance, decision making, policies (e.g., conflict of interest), and organizational inequality.