“Hope” and “change” were the keywords of President Barack Obama’s 2008 campaign, and in his farewell address on January 10, 2017, he cited the evidence that he’d delivered—from reversing the Great Recession, rebooting the auto industry, and unleashing the longest stretch of job creation in the nation’s history to winning marriage equality and securing the right to health insurance for another 20 million citizens. At the same time, and with a view to the country’s divisive polarization, he made a plea for “the decency of our people” and “the sense of common purpose that we so badly need right now.” In hindsight, it is increasingly possible to understand whether and how Obama’s legacy matched his rhetoric as well as to evaluate from various angles what his presidency accomplished and what this has meant for US politics, public policy, and civic life going forward. In some of the leading observers and scholars of US politics take up this challenge. In twelve essays these writers examine Obama’s choices, operating style, and opportunities taken and missed as well as the institutional and political constraints on the president’s policy agenda. What were Obama’s personal characteristics as a leader? What were the policy aspirations, output, and strategy of his presidency? What was his role as a political and public leader to the various constituencies needed to generate presidential power? And how did his presidency interact with other political forces? Addressing these questions and others, the authors analyze Obama’s preferences, tactics, successes, and shortcomings with an eye toward balancing the personal and institutional factors that underlie each—all the while considering how resilient or fragile Obama’s legacy will be in the face of the Trump administration’s eager efforts to dismantle it.