Trump Cashes in on Thousands of Stock Trades While Americans Get Crushed

Scott Galloway and Jessica Tarlov break down explosive new ethics filings showing that President Trump made thousands of stock trades during the first quarter of 2026, with transactions totaling hundreds of millions of dollars. While the White House insists the trades were handled through trusts and third parties, the revelations arrive alongside reports that Trump has secured a massive $1.8B fund from his own DOJ to be distributed to allies or supporters who were investigated during the Biden years. Scott and Jess also unpack growing speculation that the administration could be laying the groundwork for a future military operation in Cuba, following new sanctions and eyebrow-raising intelligence claims involving military drones. Plus: Senator Bill Cassidy became the first Republican senator in nearly a decade to lose a bid for renomination, after voting to convict Trump in his second impeachment trial. They discuss how this outcome reinforces the Trump-centrism of the Republican party, and the political risks of dissent in today’s GOP. They also dive into the increasingly bizarre Los Angeles mayoral race, where reality TV personality Spencer Pratt is gaining traction. What does his rise reveal about voter frustration, celebrity politics, and governance in the state of California? And finally: Gen Z graduates are openly booing tech executives promoting artificial intelligence in their commencement speeches. Does it mean that Gen Z is fed up with AI? Or are the boos a reaction to the generational anxiety about automation, income inequality, and the future of work?