CrossFit’s unprecedented ascent as a fitness phenomenon has attracted widespread attention due to both its unorthodox training methods and the often norm-breaking persona of charismatic CrossFit founder Greg Glassman. Although Glassman has argued that he uses a libertarian approach to guiding the CrossFit organization, Glassman’s anti-elite and often brash rhetoric, coupled with his autocratic approach to running the CrossFit corporation, evokes comparisons to authoritarian populist political leaders such as Donald Trump and Boris Johnson. In tracing the origins and evolution of the CrossFit phenomenon, this chapter explores the ways in which Glassman’s public persona, development of the CrossFit program, and frequent crusades against dominant fitness institutions are imbricated with authoritarian and populist ideologies. In concluding, I will look to the ways in which Glassman’s influence within CrossFit was diminished in recent years and how his resignation following an online racist tirade may create openings for a more equitable and democratized CrossFit.