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

“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 Global Forum returns Oct. 26–27, 2025 in Riyadh. CEOs and global leaders will gather for a dynamic, invitation-only event shaping the future of business. Apply for an invitation.

Read More
Lisa Mascaro, The Associated Press

Latest

Oregon Sues Oklahoma Transfer Over Alleged Unpaid $10K NIL Contract Buyout

The University of Oregon says one of its former football players owes it $10,000, and the school is willing to go to court to get it. The school filed a lawsuit in Lane County Circuit Court last week against Dakoda Fields, a defensive back who spent two years with the Ducks before transferring to Oklahoma

Breaking Down Ole Miss’ Strengths, Weaknesses and One Thing It Needs to Beat LSU

The hottest location in college football this year brings LSU and Ole Miss together for a matchup that should be as close are expected. Both teams are rebuilt through the transfer portal and new coaching staffs, and this Sept. 19 matchup will be the first big test for either squad. So what gives Ole Miss

What are Indiana Football’s Biggest Trap Games of 2026?

Where will Indiana be ranked to start the 2026 college football season? While debate will rage regardless of the number next to Indiana's name to start the year, the Hoosiers will likely be favored in no fewer than 11 of their 12 regular season contests. That doesn't mean there won't be challenges along the way

Green steel startup Boston Metal is doubling down on critical metals

The startup Boston Metal has raised a $75 million funding round to produce critical metals, MIT Technology Review can exclusively report.   The company has been known largely for its efforts to clean up steel production, an industry that's responsible for about 8% of global greenhouse emissions today. With the additional money, the new focus could

Newsletter

Don't miss

Oregon Sues Oklahoma Transfer Over Alleged Unpaid $10K NIL Contract Buyout

The University of Oregon says one of its former football players owes it $10,000, and the school is willing to go to court to get it. The school filed a lawsuit in Lane County Circuit Court last week against Dakoda Fields, a defensive back who spent two years with the Ducks before transferring to Oklahoma

Breaking Down Ole Miss’ Strengths, Weaknesses and One Thing It Needs to Beat LSU

The hottest location in college football this year brings LSU and Ole Miss together for a matchup that should be as close are expected. Both teams are rebuilt through the transfer portal and new coaching staffs, and this Sept. 19 matchup will be the first big test for either squad. So what gives Ole Miss

What are Indiana Football’s Biggest Trap Games of 2026?

Where will Indiana be ranked to start the 2026 college football season? While debate will rage regardless of the number next to Indiana's name to start the year, the Hoosiers will likely be favored in no fewer than 11 of their 12 regular season contests. That doesn't mean there won't be challenges along the way

Green steel startup Boston Metal is doubling down on critical metals

The startup Boston Metal has raised a $75 million funding round to produce critical metals, MIT Technology Review can exclusively report.   The company has been known largely for its efforts to clean up steel production, an industry that's responsible for about 8% of global greenhouse emissions today. With the additional money, the new focus could

Embracer Follows Ubisoft In Splitting Off New Publisher To Handle Huge IP, Tomb Raider & LOTR Included

Say hello to Fellowship Entertainment by Ben Kerry 11 hours ago Embracer Group has today announced plans to create a secondary publishing label called Fellowship Entertainment, in order to "capture the full potential of the high-quality assets" that the group currently owns. The Swedish game publisher says that it hopes to spin off Fellowship Entertainment

Tesla’s Business Has Become Much More Diversified in Just the Past Five Years. Does That Make Its Stock a Better Buy Today?

Key Points Tesla's energy generation and storage segment generated 27% revenue growth last year. The company's non-automotive segments were able to help offset a double-digit decline in auto revenue in 2025. These 10 stocks could mint the next wave of millionaires › Tesla (NASDAQ: TSLA) is known for its electric vehicles (EVs), and while they

WD sees sustainability as key business driver in an ‘AI economy’

Hard drive company WD promoted long-term operations and sustainability executive Jackie Jung to become its first chief sustainability officer in February, as it steps up sales to companies building AI data centers. Her vision: Turn sustainability into a “brand” for WD, a strategy that reduces risk for the $6 billion company (formerly known as Western

5 Business Ideas Worth Starting in 2026

If there is one thing Nigerians understand well, it is how to spot opportunity inside hardship. In 2026, that mindset will matter more than ever. The economy is tough, competition is rising, and many people are looking for smarter ways to earn, build, and survive. But even in a difficult environment, some businesses still stand