Dietrich Bonhoeffer’s perplexing and controversial shift from admitted pacifism to tyrannicide has been the source of scholarly and popular inspiration and criticism. How could an admitted Christian pacifist be involved in a plot to assassinate a political figure? Is there a way to understand and explain this phenomenon comprehensive enough to encompass all relevant data? One that takes into account the nuances of Bonhoeffer’s theology and all of the elements of his complex historical and personal contexts? This study attempts to offer an explanation by linking Bonhoeffer’s political thinking and action with his understanding of the church-world relationship and by evaluating the changes in that thought-action dyad as his life progressed. What emerges is a portrait of a bold and visionary thinker and political agent whose church-world theology, while discontinuous, is consistent enough to be authentic and yet flexible enough to meet the extraordinary challenges presented by Nazism and its intrusion into the churches. Gides suggests that it is actually Bonhoeffer’s malleable church-world thinking that ultimately distinguishes him from his theological and ecclesial contemporaries and even from the mass of German church persons and citizenry; it allowed him to confront evil by reaching beyond the constraints of traditional Lutheran thinking.