In this article, Donald Trump and the emerging ideology of ‘Trumpism’ are interpreted by drawing on perspectives from management and organization studies and related fields. The article begins by exploring key themes that emerge from a critical interpretation of Trump’s business career. Beginning as a real estate entrepreneur in the 1970s and 1980s, Trump experienced a period of mixed fortune in the 1990s, before eventually becoming a popular celebrity via the reality TV show The Apprentice. This portrayed Trump as a decisive and successful business leader. Trump’s approach to business leadership is critiqued. Emphasis is placed on seeking opportunity in economic decline, a zero-sum or negative-sum approach to profit-making and economic value, often benefitting at the expense of counter-parties. The article then explores how this approach to business was combined with previously marginal right-wing conservative ideas to project Trump as both critic and solution to bleak and troubling perceptions of American politics, economy and society. In turn this has led to a radical conservative agenda in office.