Abstract: To be sure, I offer only preliminary thoughts in this Essay. The Trump presidency is young. There are multiple challenges to multiple executive decisions and orders in courts across the country. A full treatment would take the reader into the robust literature on judicial decision making about context and pragmatism, with historical comparisons to other epochs where the challenges were comparable, even to empirical analyses of judging at different periods of time. I start with judging in “ordinary” times, the period during which I served. I then describe the challenges of judging in a time of Trump, and I conclude by illuminating the implications of those challenges perhaps for judicial education, law schools, and advocacy. The Future of the U.S. Constitution: A Symposium. April 14-15, 2017, Bloomington, Indiana. Sponsored by Indiana University Maurer School of Law, Indiana Law Journal & the American Constitution Society for Law and Policy.