Surprisingly few, if any, works on the First Amendment have explored the relation between free speech and certainty. The same holds true for decisional law. While this relationship is inherent in much free speech theory and doctrine, its treatment has nonetheless been opaque at best. In what follows, the author teases out - philosophically, textually, and operationally - the meaning of that relationship and why it is important for our First Amendment jurisprudence. In the process, he examines how the First Amendment operates to counter claims of certainty and likewise how it is employed to demand a degree of certainty from those who wish to curb or cabin free speech rights. Drawing its satirical title from words purportedly spoken by Galileo when he was persecuted by ecclesiastical inquisitors for defending the heliocentric theory of Copernicus, the Essay argues that many free speech theories (from Milton to Meiklejohn and beyond) have the net effect of constricting our First Amendment freedoms based on uncertain claims to normative benefits and equally uncertain claims of societal harm. In this general sense, many free speech theorists might be viewed as the descendants (albeit kinder ones) of Galileo’s ecclesiastical detractors insofar as they invoke their own sense of morals (or normative theories) or alleged harms to trump actual facts in order to censor speech. This problem is compounded when First Amendment lawyers must disingenuously pigeonhole their client’s speech into the doctrinal boxes compatible with normative theories. In the course of things, comedy becomes political action, erotic sexual expression becomes self-realization, offensive speech becomes cultural criticism, and imagistic commercial expression becomes consumer information. Strange as it is, in such circumstances falsity is necessarily called into the service of placing a normative face on aberrant expression. By way of a bold counter to all such theories, and duly mindful of the role of some harm in the working scheme of things, the author advances a view of the First Amendment premised less on certainty and normativity than on risk - real risks. Thus understood, the very idea of risk must be an accepted and preferred part of the calculus of decision-making, be it judicial, legislative or executive. Hence, at the philosophical level, a risk-free First Amendment is a contradiction while at the operational level it is a formula for suppression. Undaunted by the specter of criticism of his own experimental views on the matter, the author invites the kind of First Amendment risk-taking once roundly championed by Justice Louis Brandeis, a kind of freedom though uncertain of its success is nevertheless hopeful of its attainment.