Importance of leadership in fostering cohesion within organizations has received increased scholarly attention. Researchers have shown that leadership can lose its legitimacy by pursuing unpopular policies or negating the common interest of the group. However, researchers have not yet been able to establish the leadership issues that shaped the 2016 Republican primaries as President Trump's victory (despite not having the support of any living past United States president both Republican and Democrat), was indicative of masses' frustration with the political establishment, and desire for change. Using complex leadership theory as a focal lens, the purpose of this phenomenological study was to explore the experiences of members of the Republican Party pertaining to the leadership issues that shaped the outcome of the 2016 Republican primaries. Data were collected through semistructured interviews with 12 registered members of the Dallas Texas Republican Party who supported President Trump during the 2016 Republican primaries. Data emanated from the central research question of what leadership issues shaped the outcome of the 2016 Republican primaries, and were transcribed verbatim, inductively coded, and thematically analyzed. Key findings suggest that disconnect between the leadership and membership of the Republican Party, ineffective leadership, and lack of effective communication strategies, were some of the leadership issues that shaped the outcome of the 2016 Republican primaries. The implication for social change for this study is that the Republican Party may benefit from the results of this study by highlighting the importance of effective, responsive, and inclusive leadership in navigating the dynamic challenges faced by the party.