This essay analyzes how the presidency of Donald Trump presented a challenge to satirists. It argues that the ironic complexities of the Trump figure itself created an unusual situation for satire, one which required it to adapt and change in novel ways. Because Trump was both absurd and terrifying, because he was both parody and credible threat, he created a unique situation for satirists, one where many of the common tools they carry in their comedic toolkit didn’t work. Satirical irony of Trump was not a matter of irony everywhere or ironic post-truthiness; when Trump satire was at its best, it worked in two competing, yet intertwined, representational directions because it was at once a return to sincerely using irony to reveal the truth while also using irony to reveal that reality had become grotesquely and ironically absurd. This essay explores two key examples of this new satirical aesthetic, Sarah Cooper’s interpretations of Trump and Jimmy Kimmel’s use of satire to defend democracy.