<p>This text analyses the main traits of the specific “<i>Trumpian jouissance</i>” which is the driving force behind both the U.S. president’s public attractiveness and ambiguity. Donald John Trump’s political behaviour is characterised by a rather unique form of intense, transgressive pleasure called <i>jouissance</i>, which transcends normal limits and fuels his unpredictable actions, impacting both domestic and international politics. The phenomenon of <i>jouissance</i> explains both his appeal to millions and the risks posed by his leadership style. The text integrates a variety of classical and comparative sources from the history of ideas such as Augustin, Machiavelli, Jacques Lacan and Ernesto de Martino to explore how Trump’s <i>jouissance</i> manifests in his rhetoric, actions, and communicational and decisional behaviour, impacting not only the U.S. but international political culture as well. Taken together, the text integrates the genre of the classical political portrait in the sense of a personalized “political psychology” with delving deep into advanced contemporary analytical approaches of inter- and trans-disciplinary calibre such as contextual political analysis, culturo-political philosophy and historical symptomatology. This is why it can be read as a psycho-philosophical essay.</p>