Presidential impeachment is an effective instrument for controlling presidents, used to threaten governments, negotiate advantages, and gain electoral benefits. Hypothetically, a presidential impeachment process requires an offense committed by the President, which is usually stipulated in the constitution of the country under study. In this research, we analyze the cases of Brazil and Chile, exploring impeachment resolutions against Presidents Bolsonaro and Piñera (2018–2022), both qualitatively and quantitatively. In the Brazilian case, after the Federal Constitution of 1988, all Brazilian presidents faced impeachment resolutions, but Bolsonaro (2019–2022) was the most contested. In the case of Chile, President Piñera (2018–2022) was the first—following the return of democracy—to undergo an impeachment process, a precedent never before seen in Chilean democracy. The study proposes a typology based on the Constitution and Law of both countries. Thus, it employs descriptive statistics with frequency analysis to quantify the number of impeachment resolutions per presidential term and their legal grounds in both countries. We find that both institutional variables and presidential leadership influenced the accusations against both presidents.