Even though a lot has changed since 1891, it is still a regular invocation in political debates to treat the military and the courts as moderating powers. This proposal intends to recover and criticize such ideas. Going back to the Brazilian dictatorship of 1964-1985, it will explore how militaries interfered with judiciary power in order to avoid any kind of rebellion. Under the Brazilian Constitution, the tense line between civilian and military will show that to restrict political activities from such branches is a difficult task. Back to now, the proposal will unravel how both militarization and judicialization of politics will overlap in Bolsonaro’s term. This work will analyze signs of the “weak democracy syndrome” in Brazil, considering its middle income status, and focusing on a critical approach on courts and the military as actors that can work to destabilize, rather than consolidate, new democracies and their endeavor to overcome an authoritarian past and avoid its return.