This chapter explores the ways in which some progressives, in the years leading up to Trump’s election, had grown skeptical of expansive First Amendment protections, viewing them as impediments to the pursuit of equality objectives. Although some of that skepticism is understandable, the chapter details the multiple ways in which free speech and free press protections helped curtail some of Trump’s autocratic policies and practices. In doing so, the chapter argues that progressives, going forward, should not allow what it calls “First Amendment skepticism” to grow to the point that it undermines the amendment’s ability to shield democratic processes, dissenters, and vulnerable groups from future autocratic government officials in the Trump mold. The chapter ends with an exploration of future hate speech regulations. While it would be understandable for progressives, after Trump’s repeated use of hate speech, to call for greater regulations of such speech, the chapter urges progressives to be cautious in this area because of the real possibility that the regulations will be used by future government officials in the Trump mold to target and discriminate against both progressive viewpoints and racial and religious minorities.