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Freedom of thought is not directly protected as a right in the United States. Instead, US First Amendment law protects a range of rights that may allow thoughts to be expressed. Freedom of speech has been granted especially robust protection. US courts have extended this protection to a wide range of commercial activities judged to have expressive content. In protecting these rights, US jurisprudence frequently relies on the image of the marketplace of ideas as furthering the search for truth. This commercial image, however, has increasingly detached expressive rights from the understanding of freedom of thought as a critical forum for individual autonomy. Indeed, the commercialization of US free speech doctrine has drawn criticism for “weaponizing” free speech to attack disfavoured economic and regulatory policies and thus potentially affecting freedom of thought adversely. The Internet complicates this picture. This paper argues that the Supreme Court’s expansion of the First Amendment for the benefit of commercial actors lies in the problematic tension with the justification for individual freedom of thought resting in personal self-direction and identity.