Revolving door dynamics are pervasive in the United States. There are vast literatures on the revolving door and on Donald Trump, but so far, no attempts to bring these literatures together. This paper represents a first attempt to do so and answer the following questions: Can Trump’s rise be understood as a culmination of revolving door dynamics, under which managers become politicians and politicians become lobbyists? What motivated Trump to revolve, and how has Trump’s presidency affected the revolving door? The paper places Trump into the context of the revolving door and compares him with previous presidents and presidential candidates. In recent decades, revolving door activity has increased. While this suggests that the revolving door paved the way for Trump, a close examination of the evidence reveals a more complex picture. Many American businesspeople have unsuccessfully run for president. Like the businessmen-turned-presidents who preceded him, Trump is a family businessman, not a manager or a CEO of a listed company. A multitude of additional factors contributed to Trump’s 2016 win including his status as a reality TV celebrity, his charisma, and his right-wing populism: Trump is from business but not from the business establishment. In addition, Trump revolved from business into politics, rather than from Capitol Hill to K Street. Candidate Trump railed against the revolving door and pledged to drain the swamp. President Trump swamped the drain and precipitated one of the most serious crises and threats to American democracy in the country’s history.