This chapter focuses on the relationship between the American Right and the U.S. Federal ExecutiveFederal executive in the twentieth and twenty-first centuries with a special emphasis on the TrumpTrump, President Donald Presidency. It notes the evolving tensions between many of the Republican Presidents in the post-New Deal era and the bureaucracies charged with implementing programs and policies that these presidencies disliked, especially social welfare and regulatory policies supported by constituencies that typically are in opposition to the Republican PartyRepublican Party. The chapter argues that the TrumpTrump, President Donald Presidency of 2017–2021 magnified these tensions even beyond past levels. While TrumpTrump, President Donald was not particularly interested in program or policyPolicy issues as such, he was innately tuned into Republican opposition to regulation on business as a result of his own experiences in business and as a developer. However, he also found his politics of resentment emphasizing populismPopulism, xenophobia, an affinity towards religious fundamentalists, hostility to mainstream institutions and procedural regularities was to be rewarded by similar tendencies that had been emerging in the Republican Party for some time and were furthered by the Party’s strong embrace of unimpeded executive power.