The current paper is a review of leadership theory from the perspective of “strain” theories of conceptual development. From this perspective, key cultural concepts emerge to the extent that they can mediate between contradictory cultural values and symbolically capture both sides of opposing dimensions, leading such concepts to become both generally attractive and semantically ambiguous. I argue that the leadership literature, with its highly varied and sometimes contradictory conceptualizations of leadership, can be understood as such a symbolic mediation. To illustrate, the review illustrates several classical leadership approaches as attempts to capture both sides of the value dimensions of individualism–collectivism and agency–structure. While generally privileging one side of each dimension, each leadership approach tries to explain both sides, with some approaches taking borderline or hybrid positions. The potential of this approach to understanding leadership scholarship, and to building reflexivity in scholarship, is discussed.