The Rachel Maddow Show: "Rambling Trump accidentally reopens questions about an election payoff"

Date: October 14, 2025
Host: Rachel Maddow
Guests: Ezra Levin (Indivisible), Rev. David Black (First Presbyterian Church of Chicago)

Episode Overview

This episode investigates President Donald Trump's unusual praise for Egypt's authoritarian leader and the resurfacing of questions regarding possible foreign financial influence over his 2016 campaign. Rachel Maddow connects today's strange remarks by Trump in Egypt to long-standing suspicions of a secret election payoff. The episode also covers contemporary protest movements against the Trump administration’s authoritarian measures, featuring organizers and faith leaders from across the country. The upcoming "No Kings" protests and their significance, as well as strategies for resistance, are also front and center.

Key Discussion Points and Insights

1. Trump’s Egypt Comments and the 2016 Election Payoff Question

• Main point: Trump makes a bizarre reference to Hillary Clinton during an event with Egypt's President, reigniting questions about his close relationship with the Egyptian regime and potential financial ties during the 2016 election.
• Backstory: Maddow links this to a Washington Post investigation about a possible $10 million cash transfer from Egypt to the Trump campaign at a time when the campaign was financially strapped. The Justice Department, under Attorney General Bill Barr, later killed the investigation.
• Implication: Maddow suggests that under Trump, questions of self-enrichment and corruption remain disturbingly open.

Notable Quote:
"He's been my friend right from the beginning during the campaign against crooked Hillary Clinton." — Trump [05:40], as quoted by Maddow.

2. Ongoing Foreign Business and Government Deals

• Unusual official conduct: Trump arranges a meeting between the Indonesian President and Eric Trump (his son and family business manager), raising conflict-of-interest concerns.
  • Eric Trump currently promotes a Trump golf course in Indonesia, where the Trump family is finalizing lucrative new real estate boondoggles.
• Qatar dealings: Trump grants Qatar special treatment and, after negotiations, receives a $400 million luxury jet for personal use, planning to keep it as a "presidential library" asset after leaving office.
• Questionable bailout: While the US government is shut down, Trump's Treasury Secretary Scott Besant sends $20 billion to support Argentina’s failing currency—a move that primarily benefits a handful of billionaire Trump supporters.

Notable Quote:
"Trump is keeping Qatar's plane... because that's how the presidency works now under Donald Trump: you put money in his pocket, you give money to his family, and he hooks you up with basically whatever you want..." — Maddow [11:48]

3. Corruption, Authoritarianism, and American Protest

• Systemic change: Maddow details the increasing financial self-interest and repression under Trump, drawing historical parallels to other strongmen regimes.
• Protest spirit: Despite repressive tactics, American resistance is inventive and resilient, with humorous, absurdist demonstrations—especially in Portland, OR.
• Link to authoritarian history: Maddow emphasizes that self-dealing by leaders and their inner circles is always paired with hollowing out public services, repression of dissent, and targeting of protestors.
• Examples:
  • Protesters in Portland wear inflatable dinosaur and mushroom suits, play brass bands, and organize naked bike rides as mockery and resistance.
  • Protests spread from Portland to cities like Williston (VT), Memphis (TN), Columbia (MO), and Chicago.

Notable Quote:
"In Portland, Oregon, they have been laughing at the fact that Trump was trying to justify sending in the troops by saying this was a war-ravaged city, by showing in every way they know how that Portland is just as wonderful and weird as it's always been." — Maddow [15:50]

4. The No Kings Protests: Grassroots Mobilization

• No Kings Day: The upcoming October 18th “No Kings” national protest will likely surpass the June demonstration, which saw over 5 million turn out across 2,100+ locations.
• Joyful resistance: The protests are designed to be inclusive, festive, and nonviolent, emphasizing the American rejection of monarchy and authoritarian rule.
• Republican fear-mongering: GOP leaders attempt to discredit the protests as “hate America rallies,” but organizers frame them as fundamentally patriotic.
• Movement building:
  • Indivisible offers training on nonviolence, communications, and organizing for participants.
  • Focus shifts from single-day protest to strategic, sustained non-cooperation with repressive institutions.

Notable Quotes:

• "We're collectively fighting for democracy. That's big, that's serious... But fundamentally, what this is about is everybody coming together and demonstrating we don't do kings in America." — Ezra Levin [32:08]
• "If your First Amendment rights are under attack and you decline to show up because of those threats, you don't have First Amendment rights." — Ezra Levin [33:46]

5. Chicago’s Faith-Led Resistance and Legal Pushback

• Creative and spiritual protest: Chicago’s resistance to federal troop deployments includes human chains protecting churches, prayer protests, and a Eucharistic procession led by Catholic clergy denied entry to an ICE facility.
• Legal victories: Rev. David Black, injured while praying in protest, joins a successful lawsuit, resulting in a ban on the use of riot control weapons by federal agents against non-threatening press, protesters, and religious figures.
• Faith and hope: Rev. Black urges continued solidarity not just for visible community leaders, but for the invisible and captive.

Notable Quotes:

• "The story here is if this is what the agents of the Trump administration are doing to pastors, to journalists, to peaceful protesters in broad daylight, it makes me shudder to imagine what they might be doing to our neighbors who are captive behind closed doors." — Rev. David Black [42:31]
• "Faith leaders showing up at these protests to minister...we’re there to offer the witness of our faith...to offer a sense of hopefulness that justice is already in the waters..." — Rev. David Black [43:46]
• "ICE agents in Chicago community deployed tear gas on civilians yesterday. So I think we are already seeing that this notoriously boundaryless administration is still having trouble with boundaries." — Rev. David Black [45:29]

6. Rachel Maddow’s Projects and Personal Note

• Maddow shares pride in her podcast "Ultra" winning an Edward R. Murrow award and previews her forthcoming documentary premiering this Friday night on MSNBC, focused on the behind-the-scenes labor of American pro-democracy movements.

Timestamps for Important Segments

• Trump's Egypt Remarks & 2016 Election Links: [00:48] – [09:35]
• Contemporary Trump Era Conflicts of Interest/Foreign Deals: [09:35] – [15:49]
• Absurdist Protest Culture & Authoritarianism: [15:49] – [21:00]
• Nationwide Protest Movement Previews: [30:56] – [36:14]
• Ezra Levin (Indivisible) Interview: [32:06] – [36:14]
• Chicago Protests & Legal Victory: [38:01] – [46:14]
• Rev. David Black Interview: [42:20] – [46:14]
• Rachel Maddow’s Upcoming Documentary: [27:05] & [46:15]

Memorable Moments

• Trump’s out-of-context shoutout to Egypt’s dictator linking back to 2016, reopening the “$10 million payoff” theory [05:40]
• Ezra Levin encouraging all Americans to join the protest: “...We don't do kings in America.” [32:08]
• News of tactical legal victories for protesters’ rights in Chicago after faith leaders were attacked by federal agents [44:48]
• Colorful descriptions of creative resistance (dinosaurs, naked bike rides, brass bands), highlighting the uniquely American protest spirit [15:50]

Overall Tone

Rachel Maddow’s tone this episode is urgent, analytical, and spiritedly defiant. She combines serious investigative reporting with a sense of wry humor, and highlights the creativity and resilience of Americans resisting authoritarian trends. Her guests reflect this seriousness and hope, especially in their focus on strategic organizing and community solidarity.

Summary Takeaway

This episode exposes the blurred lines between presidential power, personal enrichment, and foreign influence in the Trump era, while spotlighting the widespread, inventive, and faith-fueled protests rising up in opposition. Listeners are left with both a sobering sense of the stakes and a hopeful appreciation for the diversity and determination of American resistance.