University graduate-level programs are striving to address needs for community college leaders. One way they are doing this is by strengthening their graduate programs with relevant community college courses. Increasingly, however, community college presidents are being invited to join universities in professorial roles. These new graduate faculty leaders are bringing valuable transferable skills and experiences, but they are also experiencing transitional challenges. Studies have been conducted about other university executive administrators transitioning to university professor roles, but no studies have been conducted about community college presidents making this transition. This article represents an initial effort to explore a distinct class of leaders within academe--community college presidents-turned-professor. The findings of this exploratory study of 12 former community college presidents who transitioned to graduate university professors are reported along with stories, lessons learned, and advice for successfully crossing over from the community college sector to the university one.