In this non-partisan dialogue, we examine Donald J. Trump’s deal-making during the first six months of his presidency. Rather than judging the man or evaluating his policies, we regard his actions as an opportunity to reflect on the realities of flawed and frail leaders more generally, and the impact they have on others.

We follow Isaacs’ recommendations for ‘generative dialogue’1 to overcome fragmentation in the public discourse about President Trump and in the academic literature about leadership. The dialogical method has a long tradition. Socrates engaging ordinary Athenian citizens in dialogues probing central ethical and political values and assumptions is a keystone moment in western intellectual history. In eastern philosophy, the dialogical method was used extensively in the ancient Indian scriptures, Upanishad (which literally means “sitting down near a teacher”): they portray a teacher, a disciple, peers, and scholars engaged in dialogue in the court of a King, aiming to stamp out ignorance, find meaning, and advance new ideas and institutions.