In this afternoon’s edition: President Donald Trump keeps promising cash giveaways to key midterm co͏‌  ͏‌  ͏‌  ͏‌  ͏‌  ͏‌ 
 
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October 20, 2026
 

Semafor Washington, DC

 
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This Afternoon in DC
Map of Washington, DC
  1. Trump’s midterm giveaways
  2. Hill leaders on the trail
  3. GOP vs. Trump on Russia
  4. Trump’s GSE punt
  5. Mamdani vs. AI chatbots

Michael Bloomberg gives $80 million to Democrats in final midterms stretch.

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1

Trump returns to a favorite midterm play: Giveaways

President Donald Trump
Jonathan Ernst/Reuters

President Donald Trump is turning to a favorite political tactic in the midterms homestretch: giving people money. His latest proposal is an $8 billion program for farmers struggling with steep diesel costs, which he announced last night in Kansas. The proposal echoes a series of political giveaways he’s announced recently, from one-time $90 payments for Americans enrolled in Medicare Part B, to $500 checks for some Obamacare customers, to a promise that every American will receive $5,000 should Republicans keep control of both chambers of Congress. Notably, Trump’s proclivity for direct payments isn’t new — it’s a tactic he relied on in his first term, though some of those proposals have yet to materialize.

— Shelby Talcott

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2

Reading between the lines on Hill leaders’ travels

House Speaker Mike Johnson
Aaron Schwartz/Reuters

Speaker Mike Johnson is scheduled to be in Bozeman, Montana, today to campaign with Republican House candidate Aaron Flint. It’s a sign of how much the House battlefield has shifted: Democrats are optimistic about flipping a seat that Trump won in 2024 by 11 percentage points. Republicans are still on offense in some other places, though. As for Democrats: Unlike in previous election cycles, when frontline candidates might have been skittish about appearing with party leaders like Nancy Pelosi, House Minority Leader Hakeem Jeffries and other senior Democrats have not generated much controversy. Jeffries is set to head to Texas this weekend to campaign for former sheriff’s deputy Johnny Garcia, who’s running in a San Antonio-area district redrawn to favor Republicans. He’s also stopping in California on Thursday to campaign with Rep. Derek Tran, D-Calif., whose district became bluer in redistricting.

— Nicholas Wu

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Semafor Exclusive
3

More Republicans break with Trump on Russia

Senator Katie Britt
Eric Lee/Reuters

Two more Republicans are calling on Trump to use a bipartisan law to impose penalties on Russia, joining a growing chorus who disagree with his decision to waive sanctions meant to force Moscow to end its war in Ukraine. “It is my belief that we need to use economic firepower to help drive [Russian President Vladimir] Putin to the table,” Sen. Katie Britt, R-Ala., told Semafor in Des Moines today. “I believe that Russia is at the darkest point that they’ve been at in this entire war.” Britt was campaigning with Senate candidate Rep. Ashley Hinson, R-Iowa, who expressed similar reservations about Trump’s overtures toward Putin. “I don’t think we need to be making any more deals with Russia,” Hinson said. White House spokeswoman Taylor Rogers said that “enforcing the sanctions provisions now would impede ongoing US efforts to negotiate a durable and comprehensive peace agreement between Ukraine and Russia.”

— Burgess Everett and Morgan Chalfant

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4

Trump administration punts on releasing Fannie, Freddie

Treasury Secretary Scott Bessent
Nathan Howard/Reuters

The Trump administration isn’t loosening the federal government’s grip on mortgage giants Fannie Mae and Freddie Mac any time soon. “I would imagine that the next year, the year after, we will be tackling the ownership structure,” Treasury Secretary Scott Bessent said earlier today, calling it “unclear” for now how “a change in the arrangement of the shareholder structure” would benefit homeowners. Trump said this summer that he was still considering selling some of the government’s shares in Fannie and Freddie, purchased after the 2008 financial crisis. But any move to release them from conservatorship is likely to spike mortgage rates, which Bessent called “our North Star.” Housing starts dropped 5.2% in September, the Commerce Department said this morning, as residential construction slumped. Mortgage rates, meanwhile, recently reached their highest levels since November 2023.

— Eleanor Mueller

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5

Doom loops facing doom in NYC

Zohran Mamdani
Eduardo Munoz/Reuters

New York City could be the first place in the country where consumers are protected from a “doom loop” of AI-powered customer service chatbots, per a rule proposed today by Mayor Zohran Mamdani’s administration. The rule would require businesses to connect people to a human customer service agent quickly if a chatbot cannot fulfill their requests. “When corporations force you to fight your way through an endless doom loop of AI-generated responses to speak to another human being, they’re stealing your time, money, and patience,” Mamdani said in a release. “This rule makes clear: Customer service cost-cutting can’t come at New Yorkers’ expense.” Businesses would have to disclose when customers are talking to AI and offer an “easy off-ramp” to a human representative, with violators subject to fines that would start at $525.

— Ashley Gold

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Watch This
Compound Interest

Orlando Bravo has never seen a market broken like this. On this week’s episode of Compound Interest, presented by Amazon Business, the founder and managing partner of Thoma Bravo tells Liz and Rohan why the SaaSpocalypse is over, why LBOs are so hard to do right now, and AI’s “giant sucking sound” in the capital markets. Plus, why nearly all of the private-equity money he oversees is being invested in corporate software.

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PDR

Campaigns

  • A new attack ad features Ohio gubernatorial nominee Amy Acton’s long-estranged mother broadly accusing her of lying. Acton and her mother have not spoken in nearly 50 years, since the candidate’s stepfather was charged with sexually abusing her during her childhood.
  • A small group of US national security officials are privately helping states prepare for potential Trump administration interference in the midterms. — WaPo

Courts

  • The Trump administration faces a lawsuit from the food import business over the imposition of 50% tariffs on Canadian goods.

Technology

  • Meta’s Chief Global Affairs Officer Joel Kaplan announced that he is stepping down after 15 years.

Foreign Policy

  • Ukrainian President Volodymyr Zelenskyy met with special envoy Steve Witkoff in Oslo.
  • The UK is planning to send fighter jets to defend cities and national infrastructure in Saudi Arabia amid Houthi attacks.
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Quote of the Day
“I think if I run, the president will endorse me.”

— Vice President JD Vance, asked about the 2028 election.

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Semafor DC Team

Morgan Chalfant, Washington briefing editor

With help from Elana Schor, senior Washington editor, and Laura McGann, editor

Graph Massara and Lauren Morganbesser, copy editors

Contact our reporters:

Burgess Everett, Ashley Gold, Eleanor Mueller, Shelby Talcott, Nicholas Wu, David Weigel, David Lim

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