Racially minoritized college presidents represent less than 17% of all college and university presidencies in the United States, and less than four percent are Latinx/a/o. This study explored how Latino college president men, a heavily underrepresented group in the leadership pipeline, ascribe meaning to their intersecting identities while navigating systemic oppression within higher education contexts. By applying a hermeneutical phenomenological approach, this study provided in-depth insights into how Latino men make sense of their masculine identities and leadership development. Findings revealed that influential women or mujeres influyentes in the family significantly shape the masculine identity development of Latino men. Furthermore, graduate school education played a key role in socializing Latino men in the field and was an essential step for achieving the college presidency. Additional findings underscored the biases and stereotypes that Latino men overcome throughout their career trajectories. Implications for research and practice are also included in this study.