While previous authors have broadly examined the motivations and outcomes of the philanthropic activities of organizations, the present study extends Miska et al.’s (J Bus Ethics 1–12, 2013) rationalistic approach to examine the degree to which managerial philanthropic decision-making behaviour is dominated by morality. This study also tackles the question of whether this relationship is moderated by the strength of the geographical proximity and amount of the donation within an agency framework. To probe the radical agency problem and the effect of intervention, an alternative heuristic scenario is also developed to provide evidence that managers under the same moral level show significant differences in donation intention under a variety of agency conditions. The results indicate a significant difference between the existence and non-existence of agency problems in charitable decisionmaking by managers high in idealism and relativism; however, at the same time, philanthropic behaviour is intertwined with various dilemma-related contexts. These findings bridge the gap in the literature on ethics and corporate social responsibility, and challenge current thinking on corporate governance mechanisms in this area by offering researchers and practitioners an integrated model that responds to a strong sceptical bias or a high premium placed on morality.