This is an account of the ways in which one experienced secondary school principal developed and sustained his success over a thirteen year period. The paper is organised in three parts: 1 Developing success: the first seven years; 2 Broadening and deepening: the next six years; 3 Progressive leadership trust: the person and the acts. The paper provides multi-perspective qualitative and quantitative data which complements and extends the empirical work of Bryk and Schneider (2002), Tschannen-Moran (2004) and Seashore Louis (2007). The data suggests that trust was an important feature of his success as leader and the success of the school; that it may be understood as value, disposition, behaviour and consequence; and that, to contribute to the school's success it should be exercised on individual, relational and organisational levels.