• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
PoliticsDonald Trump

During a White House meeting, Hakeem Jeffries spotted a ‘Trump 2028’ hat and asked JD Vance ‘Hey, bro, you got a problem with this?’

By
Lisa Mascaro
Lisa Mascaro
and
The Associated Press
The Associated Press
Down Arrow Button Icon
By
Lisa Mascaro
Lisa Mascaro
and
The Associated Press
The Associated Press
Down Arrow Button Icon
October 4, 2025, 7:08 PM ET
House Minority Leader Hakeem Jeffries, D-N.Y., and Senate Minority Leader Chuck Schumer of N.Y., talk to reporters outside the West Wing of the White House on Monday.
House Minority Leader Hakeem Jeffries, D-N.Y., and Senate Minority Leader Chuck Schumer of N.Y., talk to reporters outside the West Wing of the White House on Monday.Alex Brandon—AP Photo

Halfway through Donald Trump’s inaugural White House meeting with congressional leadership days before a government shutdown, the red hats appeared on the president’s desk.

Recommended Video

“Trump 2028,” they said, situated across from the seated lawmakers, Vice President JD Vance and several untouched Diet Cokes.

House Democratic leader Hakeem Jeffries leaned over to Vance, himself a potential 2028 contender, and quipped, “Hey, bro, you got a problem with this?”

The room chuckled in response.

“It was the randomest thing in the world, because we’re sitting there, we’re having a serious conversation, and all of a sudden these two red hats appear,” Jeffries recalled later at the Capitol.

“It was all so unserious,” Jeffries said, describing a roving cameraman capturing the moment. “We were there for serious reasons that it wasn’t really a big part of, you know, the discussion. It was theatrics.”

The moment was vintage Trump –- grabbing the attention and seeking to throw negotiators off their game — but it also underscored the president’s regard for Congress, a coequal branch of the government, and in particular his opponents across the political aisle.

From historic first meeting to viral trolling

What was once was considered a historic occasion –- the president of the United States convening his first “big four” meeting of congressional leaders from the House and Senate –- was reduced to another viral souvenir of Trump trolling his opponent.

And after the more than hourlong session, Trump failed to strike a deal with the leaders to prevent a federal government closure.

“We don’t want it to shut down,” Trump said at the White House the next day, hours before the midnight deadline.

This wasn’t just a routine meeting of the president and congressional leadership. It was the first time Trump had gathered the leaders of Congress, more than eight months into his presidency — and the first time he and Jeffries had officially met.

But more surprising was how little came from it.

Health care funds up for debate as president listens

During the White House meeting, Jeffries and Senate Democratic leader Chuck Schumer laid out their arguments for saving health care funding as part of the shutdown talks.

Trump said very little, doing more listening than talking, the leaders said.

“He didn’t seem to know about the health care premiums going up so much,” Schumer said.

With the Republican leadership, House Speaker Mike Johnsonand Senate Majority Leader John Thune, the conversation ranged across their views of the health care situation.

“Lively,” as Thune said later.

The discussion included the Democrats’ demands to ensure subsidies to help people buy private insurance on the exchanges run by the Affordable Care Act are made permanent. The subsidies were put in place during the COVID-19 pandemic and are set to expire at year’s end, spiking premiums as much as double, in some estimates.

The conversation also touched on the new rural hospital fund that is important to Republicans, set up under Trump’s big bill as a way to compensate for its cuts to Medicaid health care providers.

Johnson said Trump showed “strong, solid leadership. He listened to the arguments.”

Trying to catch the president’s attention

This is the best the Democrats could have hoped for — to have an airing before the president that began to turn the dial toward their demands. And it is what the GOP leaders had tried to avoid as each party tries to blame the shutdown on the other.

Johnson had suggested Trump back out of an initial meetingwith the Democrats — after the president had agreed to one — arguing it would be a “waste of time.”

But Trump relented, and granted them Monday’s closed-door Oval Office session.

The Democrats have been here before. During Trump’s first term, the president repeatedly negotiated deals with the Democrats — “Chuck and Nancy,” as he called Schumer and Speaker Emerita Nancy Pelosi — to fund the government, raise the debt limit and achieve other goals.

Those bargains by Trump frustrated his own Republican Party.

Republicans, aware of that history, are trying to steer the conversation in a different direction, leaving the door open to discuss the health care issue with Democrats later — once the government has reopened. They also took issue with the characterization of Trump as unaware of the depth or magnitude of the health care situation.

“I’m highly skeptical the president was hearing about it for the first time,” Vance said afterward.

One Republican unauthorized to publicly discuss the private meeting and granted anonymity to do so said Schumer’s suggestion that Trump didn’t know about the subsidy problem was overblown.

So far in his second term, the president has been able to accomplish his priorities either on his own, with executive actions and the Elon Musk-led cuts that tore through federal offices, or with a compliant Congress passing his signature tax breaks and spending cuts bill, commonly called the One Big Beautiful Bill Act, that is also fueling his mass deportation agenda.

But Washington doesn’t run on the White House alone, and Congress is not a majority-takes-all institution. Turning most bills into laws requires the give-and-take of bipartisan compromise, particularly in the Senate, and particularly when it comes to the annual appropriations needed to keep government running.

Then came the sombrero taunts

Hours after the lawmakers left the meeting, Trump’s team posted a fake video that showed Jeffries adorned in a sombrero with a faux mustache standing beside Schumer outside the White House. It was widely seen as racist.

“When I was practicing law, there was a Latin phrase that was always one of my favorites,” Jeffries said back at his office at the Capitol. “Res ipsa loquitur. It means: The thing speaks for itself.”

“We had a full airing of our positions on Monday, which should have set the baseline for a follow-up conversation from the administration to try to reignite a meaningful bipartisan path toward funding the government,” he said.

“Unfortunately, the president’s behavior subsequent to the White House meeting deteriorated into unhinged and unserious action.”

The Fortune 500 Innovation Forum will convene Fortune 500 executives, U.S. policy officials, top founders, and thought leaders to help define what’s next for the American economy, Nov. 16-17 in Detroit. Apply here.
About the Authors
By Lisa Mascaro
See full bioRight Arrow Button Icon
By The Associated Press
See full bioRight Arrow Button Icon

Latest in Politics

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Politics

Trump at a podium
PoliticsIran
Trump will address the nation about the Iran war on Wednesday. Here’s what to expect
By Eva RoytburgApril 1, 2026
7 hours ago
Luigi Mangione’s federal trial has been pushed back to October in killing of UnitedHealthcare CEO
LawMurder
Luigi Mangione’s federal trial has been pushed back to October in killing of UnitedHealthcare CEO
By The Associated Press, Michael R. Sisak and Larry NeumeisterApril 1, 2026
10 hours ago
trump
CommentaryEPA
The EPA just valued a human life at $0. That’s not just a moral crisis — it’s a market crisis
By Andrew BeharApril 1, 2026
15 hours ago
pelosi
CommentaryElections
Congress has a lower approval rating than Hitler in some polls. And we just keep voting for the same 2 parties
By Stu StrumwasserApril 1, 2026
17 hours ago
Photo: Donald and Melania Trump.
PoliticsMarkets
Trump has no good options in Iran—here are 5 of them ahead of his speech to the nation tonight
By Jim EdwardsApril 1, 2026
17 hours ago
MUSCAT, OMAN - MARCH 22: The Albina Bulk carrier sits anchored on March 22, 2026 at Sultan Qaboos Port in Muscat, Oman.President Donald Trump had threatened to attack Iran's energy infrastructure if it did not end its de facto blockade of the Strait of Hormuz by just before midnight GMT of March 23. A subsequent statement from President Trump said the U.S. and Iran had held "very good and productive conversations regarding a complete and total resolution of our hostilities in the Middle East," and that he would postpone any attacks on Iranian energy infrastructure for five days. Maritime traffic through the strait, which conveys about 20% of the world's oil and gas, has mostly come to a halt after the joint U.S.-Israeli war with Iran that began on February 28.
EnergyIran
Trump has a labyrinth of bad options in the Strait of Hormuz. Here’s why some warn that walking away could transcend ‘our defeat in Vietnam’
By Jordan BlumMarch 31, 2026
1 day ago

Most Popular

Jerome Powell says the $39 trillion national debt is ‘not unsustainable,’ but warns the trajectory ‘will not end well’
Economy
Jerome Powell says the $39 trillion national debt is ‘not unsustainable,’ but warns the trajectory ‘will not end well’
By Fortune EditorsMarch 30, 2026
2 days ago
Two-thirds of parents say their adult Gen Z kids still rely on them financially  for support—even though it's putting them under strain
Success
Two-thirds of parents say their adult Gen Z kids still rely on them financially  for support—even though it's putting them under strain
By Fortune EditorsMarch 31, 2026
1 day ago
A man used AI to call 3,000 Irish bartenders to track the cost of Guinness. Now pubs are lowering their prices to compete
AI
A man used AI to call 3,000 Irish bartenders to track the cost of Guinness. Now pubs are lowering their prices to compete
By Fortune EditorsMarch 30, 2026
2 days ago
Kevin O'Leary says if you earn $68,000 a year and follow this rule, you'll retire a millionaire
Personal Finance
Kevin O'Leary says if you earn $68,000 a year and follow this rule, you'll retire a millionaire
By Fortune EditorsMarch 31, 2026
1 day ago
Hiring just hit a level not seen since the economy was ‘closed down literally’ during COVID, top economist says
Economy
Hiring just hit a level not seen since the economy was ‘closed down literally’ during COVID, top economist says
By Fortune EditorsMarch 31, 2026
1 day ago
Mark Carney lays down the gauntlet: 'It is essential that the next CEO of Air Canada is bilingual'
C-Suite
Mark Carney lays down the gauntlet: 'It is essential that the next CEO of Air Canada is bilingual'
By Fortune EditorsMarch 30, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.