Despite boasting its self-characterization as the "land of the free," US American "freedom" is, at times, tainted with historical amnesia, hypocrisy, and inhumanity. This article examines today's socio-political climate by drawing from de Tocqueville's (2003) prediction that American democracy is a tyranny of the majority. Because tyranny relies on gaslighting and dismissing facts, no definitive portraiture of freedom is made; therefore, the tyrannized wonder whether they are truly living within freedom or, instead, in collective submission to its illusion. This article examines this phenomenon in order to investigate how whiteness (re)produces conditions of disillusionment and tyranny. By employing hermeneutics of whiteness as a methodology, the authors investigate how whiteness infiltrates thoughts/epistemology, speech/rhetoric, emotions/emotionality, and nationalistic symbols/semiotics. The authors analyze implications for US education and offer a plea for all to consider.