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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
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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.

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“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.”

Fortune Brainstorm AI returns to San Francisco Dec. 8–9 to convene the smartest people we know—technologists, entrepreneurs, Fortune Global 500 executives, investors, policymakers, and the brilliant minds in between—to explore and interrogate the most pressing questions about AI at another pivotal moment. Register here.
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By Lisa Mascaro
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