By placing the relationship between the United States and Brazil under President Donald Trump into long-term and recent historical and diplomatic context, this chapter argues that relations between the two countries under Trump are best interpreted as the latest manifestation of a two-century effort to impose U.S. hegemony. From Brazilian independence in 1822 until the election of Luiz Inácio Lula da Silva in 2003, the relationship between Brazil and the U.S. was characterized by U.S. economic and diplomatic imperialism on the one hand and Brazilian efforts to promote its own independence, development, and prestige on the other. Under the government of Lula and his successor, Dilma Rousseff, Brazil, like other Latin American “pink tide” countries, made even greater efforts to assert its sovereignty. In its most provocative intervention, this chapter argues, based on a variety of intriguing public and leaked statements from U.S. and Brazilian actors, that the U.S. collaborated with Brazilian authorities to neutralize Lula’s Workers’ Party (PT) and put a more pliant government in power. Seen in this light, the recent rapprochement between Trump and new Brazilian president Jair Bolsonaro is unique not because the U.S. expects Brazil to be a faithful lackey of American foreign policy, but rather due to the obsequiousness of Bolsonaro in his efforts to gain the approval of a country he deeply admires. More broadly, the chapter uses the Brazilian case to argue that in recent years, the U.S. has not retreated from empire, but rather regrouped and struck back, using new, less obvious means to attempt to impose the interests of its political and corporate class on the rest of the world.