Former President Donald Trump frequently promised to restore “free speech,” yet rulings in at least 75 cases suggest his administration actively stifled it. These cases involve challenges to actions taken by the Trump administration that critics argued suppressed speech. Officials within the Trump administration consistently dismissed unfavorable judicial decisions as the work of “activist” judges overstepping their authority and obstructing presidential power. This rhetoric aimed to discredit the judiciary while the administration pursued policies limiting expression. The rulings demonstrate a pattern of the administration attempting to control narratives and limit dissenting voices. The contradiction between Trump’s public statements and his administration’s legal battles highlights a complex relationship with the First Amendment. These judicial decisions underscore ongoing debates about executive power and the protection of free speech.