This thesis examines Donald Trump\u27s disruption of political satire. The history and format of the White House Correspondents\u27 Dinner provides a framework for understanding the shifting relationship between the president\u27s administration, the journalists who cover that administration, and political comedians. These three groups cross paths at the White House Correspondents\u27 Association\u27s annual dinner, which the president traditionally attends and where a headlining comedian entertains guests with a monologue. Trump\u27s decision to skip the Correspondents\u27 Dinner set the stage for a renegotiation of the traditional relationship between president, press, and performer. As President Trump continues to attack both journalists and late-night hosts, the two groups continue to discover common ground. The work of comedians looks increasingly like news reporting, and late-night shows have developed a format based on extensive research and journalistic storytelling. These comedians, however, insist they are only comedians, and dismiss the idea that they are responsible for any political outcomes. Controversy surrounding the 2018 Correspondents\u27 Dinner centered on this question of the role of comedy. Tracing the history of the 2006, 2011, and 2017 Correspondents\u27 Dinners provides a context for examining Michelle Wolfs consequential monologue at the 2018 Correspondents\u27 Dinner, which highlighted both the potential and the limitations of political satire in Donald Trump\u27s political world