As Brazil becomes one important example of democratic decay, this paper explores the maintenance of an authoritarian mindset in some crucial moments of Brazilian recent history. It shows how this authoritarian mindset has had a vigorous capacity of reinventing itself as democratic in both explicitly authoritarian and democratic moments. Brazil has a fascinating history of transition to democracy and improvement of the rule of law. However, some impactful authoritarian legacies have not been overcome and have impaired the development of the country. This is the paradox many of the Brazil’s recent developments reveal: on one hand, there is visibly an institutional improvement, so the obedience to the “rule of law” has indeed become a more serious concern; on the other hand, that authoritarian mindset is also gaining momentum, as currently observed with the rise of Jair Bolsonaro as President. The future of Brazilian democracy depends on which side of this paradox will prevail.