Recognizing leadership as a social influence process (Treadway et al., 2012), the purpose of this dissertation was to develop and empirically evaluate a moderated, multi-mediational model linking leader political skill, leader-subordinate relational quality, and multi-target benefitting workplace outcomes. Specifically, it was hypothesized that leader political skill would be related to both the leader and the subordinate in the form of intrapsychic (i.e., within individual) and interpersonal (i.e., between individuals) effects. These effects were hypothesized to influence the development of high-quality leader-subordinate work relationships, which, in turn, were hypothesized to influence a number of leader-, subordinate-, and organization-benefitting outcomes. Utilizing a sample of 717 subordinates and 414 leaders representing 288 unique dyads from public sector organizations, results revealed that leader political skill was positively related to each of the intrapsychic effects, but the intrapsychic effects were not related to work relationship quality. However, post-hoc analyses revealed that the intrapsychic effects of political skill were positively related to leaders' participation in transformational leadership behaviors, which were in turn related to work relationship quality. Moreover, work relationship quality was significantly related to the majority of auspicious workplace outcomes. Unfortunately, the data revealed that subordinates could not empirically distinguish between the interpersonal effects and work relationship quality; therefore, this precluded the examination of these hypothesized relationships. Regardless, this dissertation answers a number of recent calls for continued or renewed leadership research, including those for increased research on leader style (House & Aditya, 1997), political theories of leadership (House & Aditya, 1997), and examinations of leader traits/characteristics influencing the leadership process (DeRue et al., 2011). Directions for future research and implications for science and practice are discussed.