This paper is in four parts. First, it undertakes an in depth analysis of contemporary cultural concerns—politicians’ expenses in UK, Catholic Hierarcy’s handling of child sexual abuse in Ireland and the crisis of leadership in banking internationally from the perspective of leadership: the creation, corrosion and corruption of rules. Second, the role of rules in selected leadership literature will be critically examined and the roots of rule-breaking rhetorics carefully scrutinised with particular emphasis on the shaping influences of such discourses on conceptions of leadership excellence, orthodoxy and transformation. Third, vignettes from the professional deliberations of school principals will be critically analysed to gain insight into how professionally responsible leadership is understood and enacted by those who regularly navigate its eddies of uncertainty. Fourth, the concluding section will draw together what appear to be key ingredients of professionally responsible leadership that hold in productive synergy the art of legitimate compromise with personal and professional integrity in decision-making, while briefly outlining the implications of such deliberations for concepts of leadership and professional learning.