DC is about to pick new leaders. Trump is watching.

Washington will soon enter a new chapter after voters pick the capital’s first new mayor in a dozen years and its first new Congressional delegate since 1991. And no matter who wins Tuesday’s primaries, they’ll be on a collision course with President Donald Trump.

The frontrunners in both races have hinged their campaigns on opposition to Trump, who since returning to office has chipped away at Washington’s autonomy and sought to remake parts of the city in his image. Mayor Muriel Bowser, who has led the city since taking office in 2015, has taken a pragmatic approach to working with the president in an apparent effort to avoid further furor. Del. Eleanor Holmes Norton has represented the District since 1991 and condemned Trump's actions in strongly worded statements, but the 89-year-old has dodged the spotlight amid questions about her acuity and ability to serve.

The candidates running to replace them say that’s far from enough.

In interviews with POLITICO, those leading candidates emphasized that they hoped to find common ground with the Trump administration and coordinate where possible, especially on projects that could jumpstart Washington’s sluggish economy. But they all drew a red line at Trump’s extraordinary law enforcement actions, including sending in the National Guard indefinitely and surging federal immigration agents in coordination with local police.

“Washington, D.C., residents want and deserve a mayor who's going to stand up and fight back, and that's what I'm bringing,” said Kenyan McDuffie, a relatively moderate, pro-business former D.C. Council member who is polling second in the mayor’s race. He has pledged to end coordination between the Metropolitan Police Department and ICE on his first day in office.

Janeese Lewis George, a D.C. council member who is polling more than 10 points ahead of McDuffie, has taken an even more adversarial posture against the president. She told POLITICO she would “actively tell our employees to resist” if Trump again federalized the MPD, adding that she would work with D.C. Attorney General Brian Schwalb “to defend D.C.”

Trump is already making known his displeasure — particularly with Lewis George, a democratic socialist whose platform and campaign are reminiscent of those of New York City Mayor Zohran Mamdani. Asked last week about the possibility of Lewis George winning the primary, Trump told reporters in the Oval Office: “I wouldn’t like it.”

“Maybe we’ll take back Washington, run it on a federal basis,” he continued. “We won’t put up with it. We’re not gonna lose our businesses.”

Lewis George’s campaign almost immediately cut Trump’s comments into an ad. “Look, we’re not going to get ICE off our streets by fearing this president,” she said in response. “We’re not going to protect our rights, or Home Rule, by complying in advance. Threatening Home Rule because you don’t like how residents are voting is an attack on democracy itself. The people of D.C. elect their mayor, and they want someone who’s gonna stand up to Donald Trump.”

There’s a similar sentiment among the leading delegate candidates.

Robert White, a city council member and one of two frontrunners in the delegate race, described Trump’s surge of federal agents and National Guard troops to the city as “lawlessness” and “the opposite of public safety.” He said he would seek to build a coalition in Congress to “push back in every way.”

Brooke Pinto, a fellow council member and the other delegate frontrunner who has centered public safety in her campaign, said the administration’s use of National Guard troops and ICE agents have not helped the city. “While I am very committed to advancing public safety in the District of Columbia, what we're seeing from the Trump administration undermines those efforts,” she said.

That type of messaging is politically savvy in a city with an electorate that heavily supported Kamala Harris in 2024 and whose lives have been directly impacted by the president’s grip over Washington — from the troop surge to his sweeping cuts to government programs and razing of the federal workforce, which have severely contracted the District’s economy. That’s not to mention his efforts to splash his name and face across federal buildings, and mounting moves to beautify portions of the city and stand up ambitious architectural projects.

“When politicians try to interfere with our local public safety, when they are sweeping up unhoused residents, cutting jobs, when they are pushing policies that negatively affect our local economy and driving up overall costs of everything from gas to housing, I'm going to fight back,” McDuffie said.

But it sets the candidates — whoever wins — in explicit opposition to Trump, who has consistently sought to bring his enemies to heel whenever he gets the chance. The president has several levers at his disposal if he chooses to retaliate against Washington, from another federal law enforcement surge to using his influence over Congress to weaken D.C. Home Rule. The city also depends on the federal government for high-profile projects that would improve public spaces and bring jobs to the District, including upgrades to Union Station and the redevelopment of the RFK Stadium campus.

Asked how the White House is preparing for a potentially more adversarial mayor and delegate, a spokesperson referred POLITICO back to Trump’s Oval Office comments.

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