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We have a First Amendment right to criticize the government. But this freedom does not translate into a right to criticize one’s boss even if, as for millions of Americans, one’s boss happens to be a government employer. Public employee speech doctrine has long established wide latitude for public employers to supervise their workers. Employees must show at the threshold that their speech was on a matter of public concern and not an internal workplace matter. The Supreme Court’s pronouncements over the last decade in a related doctrinal area, however, have unsettled the line demarcating workplace speech. In its agency fees cases, the Court has repeatedly stated that when a union speaks on matters of interest to the general public, even internal workplace matters, it triggers constitutional scrutiny. Taken at face value, the new definition of matters of public concern in a government workplace provides a basis for employees to claim expanded free speech protection. This Note is the first scholarly work to propose how public employees will claim expanded speech protection on the basis of the Court’s holding in Janus v. American Federation of State, County, and Municipal Employees (AFSCME). The expanded definition of matters of public concern is likely to destabilize public employee speech doctrine, causing uncertainty for employers as to how to supervise employees in compliance with the First Amendment.