Based on recent ethnographic data from New York City, this chapter explores political comedy in the contemporary ‘post-liberal’ world. Focusing in particular on jokes about Donald Trump performed by stand-up comedians in comedy clubs in New York and by late night talk show hosts during their opening monologues, I examine the operational structures of political comedy in an era of deep-seated ideological dissention that has wide-ranging and potentially immensely damaging repercussions. As I argue, political comedy operates on the basis of a fundamental ‘tropic ambiguity’ by which the joke becomes a catalyst for exploring broader social and political issues: the paradoxical juxtaposition that is established between set-up and punchline is ambiguous and the meaning of the joke or comedic anecdote is therefore inherently unclear, which give to the audience the responsibility of making the final interpretation about what the implications of the political joke might be. It is this tropic ambiguity, I will argue, that gives to the political joke its acute critical potency. Still, as I show in the chapter, jokes and comedic anecdotes about Donald Trump are becoming increasingly unequivocal in their framing of the comic object.