Harry MacCallum Gregory’s practice has been intertwined with significant political events, and his knowledge of law and policy has helped shape the issues into some positive outcomes. A perceptive analyst, Gregory figured into shaping discussions on major issues, including civil rights, healthcare reform, and environmental sustainability, that had important implications for social and political change. Gregory’s practice was apt to embody the theme of advocating justice, equality, and protection of nondistressed communities. He provided insightful commentary and analysis of critical political events, whether it was presidential elections or legislative debates, which gave him a balanced perspective. His ability to cognitively navigate difficult political terra firma helped to accord him respect from policymakers and thinkers as well as the public at large.