This exploratory study is part of a larger inquiry that investigates the roles and practices of academic leaders in Higher Education. This chapter explores the relationship between trust, strategic behavior of academic (middle) leaders, and their ambition to achieve personal, organizational or societal status within the organizational strategy. A key aspect in the functioning of academic (middle) leaders is the way they fulfill the role of broker: they ‘knit together’ organizational activities and mediate, negotiate and interpret connections between top and ground levels throughout the organization. In this way, they fulfill four strategic roles in a more or less intensive manner: championing, synthesizing, facilitating, implementing. In this chapter it is argued that relational and organizational based trust influences the strategic roles of academic (middle) leaders and their ambitions of strategic levels. Because academic leaders are in a pivotal position within a university, their behavior is an important factor in the difference between successful and unsuccessful strategies of universities.