President Trump’s recent embrace of economic proposals run sharply against free-market orthodoxy, exploring three headline-grabbing ideas: capping credit-card interest rates, banning institutional investors from buying single-family homes, and restricting dividends and stock buybacks by defense contractors. Why is a Republican president is advancing policies more commonly associated with progressive populism? Drawing on economic history, constitutional law, and real-world market behavior, Epstein argues that price controls, capital restrictions, and politicized contracting consistently backfire, harming consumers, workers, and innovation alike. The conversation situates Trump’s proposals within a broader populist strategy, assesses the political incentives behind them, and warns that ignoring basic economic lessons risks repeating some of the most durable policy failures of the past.