Rick Wilson's The Enemies List

What really fueled Donald Trump’s 2024 comeback? In this episode Rick sits with journalist and author Alex Isenstadt to discuss his new book, Revenge: The Inside Story of Trump's Return to Power. They dive into Trump's campaign strategy, his ability to harness cultural resentment, and the political maneuvers that secured his victory. From his outreach to young male voters through podcasts to the decisive role of figures like JD Vance and Elon Musk, Isenstadt provides an insider's perspective on how Trump reshaped his movement. They also explore the psychological impact of the assassination attempt in Pennsylvania and how it further galvanized his supporters.

The fight for civil rights wasn’t just waged in the streets, it was built in classrooms led by unsung heroes. In this episode Rick speaks with author Elaine Weiss about her new book, Spell Freedom: The Underground Schools That Built the Civil Rights Movement. They discuss the little-known history of citizenship schools—grassroots educational programs in the 1950s and 60s that empowered Black Americans to pass literacy tests, register to vote, and fight systemic oppression. Weiss sheds light on the broader civil rights movement, the institutional barriers activists faced, and the enduring importance of civic education in today’s political landscape. Elaine's book, Spell Freedom: The Underground Schools That Built the Civil Rights Movement, available now.

The balance of power in American democracy is being tested like never before. In this episode Rick is joined by legal expert and author Tristan Snell to discuss the latest legal battles surrounding Trump, the Supreme Court’s role in shaping executive power, and the broader implications for American democracy. They break down key cases, including the limits of presidential immunity, the Administrative Procedure Act, and the growing constitutional crisis if Trump defies court rulings. Visit Tristan's Substack at tristansnell.com.

America’s political landscape is shifting in dangerous ways. On today's episode Rick is joined by journalist and author Garrett Graff to dissect the current crisis in U.S. democracy, where unchecked power, disruptive media narratives, and the staggering influence of figures like Elon Musk are redrawing the rules of governance. Graff introduces his incisive newsletter, Doomsday Scenario, which reimagines American news as if it were unfolding overseas—casting a stark light on the nation's mounting instability and the erosion of federal institutions. Subscribe to Garrett's newsletter at doomsdayscenario.co.

Will Trump and the House GOP end up becoming the dogs that caught the car? What happens with the impending shutdown - and should Democrats try to keep the government open? And why all those horrible polling numbers for Trump in House seats really don't matter to Trump and Elon. It's all a race - can Trump derail democracy before we win back the House? What can we do to stop it?

Gen Z is at a political crossroads, and the battle for their votes is intensifying. In this episode Rick speaks with Gen Z political commentator Dash Dobrofsky to discuss the shifting political landscape among young voters. Dash shares his journey into political activism, the impact of social media on shaping narratives, and the growing influence of right-wing messaging on Gen Z—particularly young men. They dive into economic frustrations, media strategies, and the urgent need for Democrats to improve their branding and messaging. With insights on the future of digital political engagement and the 2028 election, this conversation sheds light on the evolving battle for young voters' attention and trust.

We have entered a whirlwind of chaos and controversy as the new order attempts to reshape the American political landscape. In this episode Rick sits with Andrew Egger, chief White House correspondent for The Bulwark, to dissect the early months of Trump's second first term in the White House. They explore how a disruptive, Doge-fueled approach is reshaping federal agencies, from hasty cuts in key national security institutions to internal power struggles, and debate the evolution of conservative politics. And of course, Rick adds to the Enemies List.

The chaos isn’t slowing down, it’s accelerating. In this episode Rick is joined by Will Saletan from The Bulwark to dissect the unfolding turmoil in D.C. and beyond. They discuss Elon Musk's growing influence, Trump's erratic decision-making, the GOP’s shift toward isolationism, and the potential global and domestic fallout from these radical changes. From economic instability and foreign policy upheaval to the looming dangers of reckless governance, the two break down the woodchipper-like destruction of key institutions and its long-term consequences.

Is America’s economic power a weapon, or a ticking time bomb? In this episode Rick is joined by Edward Fishman, author of Choke Points: American Power in the Age of Economic Warfare. They dive into the rise of economic warfare as the primary battleground for global powers, exploring how tariffs, sanctions, and export controls have reshaped international relations. Fishman discusses the risks of Trump's aggressive trade policies, the potential fallout of economic isolationism, and the unintended consequences of a fractured global economy. Edward's book, Choke Points: American Power in the Age of Economic Warfare, available for pre-order now.

Can Democrats win back rural and working-class voters before it’s too late? In this episode Rick Wilson sits down with Adam Frisch, former congressional candidate from Colorado, to discuss the state of the Democratic Party and its challenges in connecting with rural and working-class voters. Frisch shares insights from his campaign against Lauren Boebert, emphasizing the importance of dignity, economic messaging, and breaking through the Democratic Party’s institutional mindset. He also critiques the party’s communication strategies and highlights the need for candidate-led campaigns. Together, they explore the impact of Trump’s policies, the role of soft power, and the looming economic consequences that could shift voter sentiment in the coming months.

USAID being dismantled before our eyes is just the beginning. In this episode Rick is joined by Josh Rogin, Lead Global Security Analyst for Washington Post Intelligence, to discuss the shocking dismantlement of USAID by Elon Musk and Donald Trump. They explore the broader implications of this decision, including the erosion of America’s global influence, the potential humanitarian crisis, and how adversaries like China and Russia stand to benefit. The conversation also delves into Trump’s complicated relationship with Xi Jinping, the future of Taiwan, and the geopolitical risks of a second Trump presidency—particularly regarding Ukraine, where Vladimir Putin is poised to take advantage.

Today we tackle a new age of politics and propaganda as Rick is joined by philosopher and author Jason Stanley. The two discuss the manipulation of language, propaganda, and the rise of authoritarianism in modern politics. They examine how global far-right movements are using nationalism, immigration fears, and media control to consolidate power, drawing parallels to historical fascist strategies. The conversation delves into the role of education, corporate-state alliances, and the erosion of democratic norms, highlighting the dangerous shift toward kleptocratic authoritarianism. Stanley also discusses his latest book, Erasing History, and the ongoing battle for truth in an age of disinformation. Jason's book, Erasing History, available now.