This book examines challenges to the First Amendment during the Trump Era. The Trump Era is characterized first and foremost by a president who has publicly challenged First Amendment free speech and press principles, norms, and rights. Candidate and now President Trump has declared “war” on the institutional press, publicly condemned individual protesters, blocked Twitter critics, made derogatory comments about race and gender, and exhibited a general intolerance of criticism and dissent. These events have transpired in an era also characterized by a diminished institutional press, mass digitization of speech, generational uncertainty about the benefits of freedom of speech, deepening social and cultural cleavages, the rise of intense and negative partisanship, and the proliferation of hateful expression. Together, these conditions pose serious threats to our First Amendment traditions concerning freedom of press and speech. In particular, they pose a distinctive threat to the creation and preservation of a culture of dissent, without which democracy itself is imperiled. Although some of the era’s conditions and challenges are new, many of the First Amendment concerns they raise are not. The book thus looks to historical events to highlight both what is unique about the Trump Era and what is historically familiar. In terms of rebuffing authoritarian impulses and resisting pressures to conform, the lessons of the past point the way forward.