Bloodbath this fall

Virginia Republicans worry about their gubernatorial candidate who invoked slavery when criticizing DEI

Winsome Earle-Sears has had a sluggish start to her campaign. Republicans are urging her to turn it around — or face a bloodbath this fall.

By Brakkton Booker, Liz Crampton and Ben Jacobs

Virginia Republicans are bracing for November with a growing sense of doom.

The GOP already faced a tough climate in this year’s elections thanks to tech billionaire Elon Musk’s war on the state’s robust federal workforce. Then came a bitter, intraparty feud over Republicans’ lieutenant governor candidate. Now, some Republicans are privately expressing concerns about the viability of their gubernatorial nominee, Winsome Earle-Sears.

“With the demographics of Richmond, in an off year with the Republican White House, it’s going to be tough,” said longtime Virginia Republican strategist Jimmy Keady. “To be a Republican to win in Virginia, you have to run a very good campaign. You’ve got to have [tailwinds] and the Democratic candidate’s got to make a mistake.”

Virginia Republicans always knew this would be a challenging election year. In the gubernatorial race, Democrat Abigail Spanberger is a well-positioned candidate with a record of winning competitive races.

But Virginia Republicans are growing increasingly worried about Earle-Sears’ slow start to the campaign. According to nearly a dozen Republican strategists and officials in the state, her sluggish fundraising, a controversial speech in which she compared Diversity, Equity and Inclusion programs to slavery and her frosty relationship with MAGA rising star John Reid, who is running for lieutenant governor, could make a bad year worse.

“A lot of us are looking at it and saying, ‘I’d do it differently,’” said a senior GOP staffer granted anonymity to speak freely. “She’s a good person, she’d make a good governor, and she’s just not as strong of a candidate as we’d like to have.”

Recently, her campaign sent a fundraising email that tied American slavery to DEI. “Slaves did not die in the fields so that we could call ourselves victims now in 2025,” said the email, signed by Earle-Sears, who is looking to become the state’s first woman and second Black governor. The email went on to say that “Democrats think minorities can’t succeed without DEI” and highlights Virginia as “the former capital of the Confederacy.” The campaign said it was not responsible for the email and declined to say who was, but a video shared with POLITICO showed her making similar statements at an event in 2023. The text is still posted on her campaign’s WinRed fundraising page.

“Winsome is a strong candidate, running a smart campaign, and will win the governorship in November,” said campaign press secretary Peyton Vogel. “We’ll keep our focus on things that matter — like continuing to break fundraising records, earning endorsements, and sharing with Virginians the dark realities of Abigail Spanberger’s two-faced balancing act.”

When watermarked stock photos appeared on the issues page of her campaign website — an internal oversight suggesting not everything the campaign produces is fully vetted — Chris LaCivita, a former senior adviser to President Donald Trump’s 2024 campaign who has worked for a number of high-profile Virginia Republicans, called campaign staff “amateurs.”

Others have criticized Earle-Sears for not firing back more forcefully when a Democratic-leaning group last month released audio of her saying she believes the Trump tariffs were positive for the economy in an effort to paint her as out of touch with many Virginia voters.

And there are questions about her previous hard-line stances on socially conservative issues that the party has been trying to shed to better play in the blue and affluent suburbs of Washington. Earle-Sears has written her opposition on bills and constitutional amendments that she is constitutionally required to sign. The Virginia Mercury newspaper reported on a handwritten note Earle-Sears wrote expressing that she was “morally opposed” to an amendment that enshrined abortion in the state constitution. And the Virginia Scope found she added a similar note to anti-LGBTQ+ discrimination bill, too.

“There are those kinds of glitches, [when] you see them, you manage them, you get through them, and you go to the next thing,” said Kay Coles James, the former head of the conservative Heritage Foundation with deep ties to GOP circles in Virginia. “I am not in a panic mode at this point.”

Virginia Republicans maintain that it’s early — and even some of her harshest critics believe there’s time for her to turn it around. There’s some evidence that Earle-Sears is heeding those calls. The campaign launched its first ad this month, highlighting her immigrant roots, her service in the Marines and her willingness to buck traditional Republican orthodoxy. She was set to travel to Dallas on Monday for a fundraiser headlined by former President George W. Bush, according to a screenshot of an invitation reviewed by POLITICO.

The campaign has also ramped up its attacks on Spanberger by amplifying her recent comments that she doesn’t support a full repeal of Virginia’s right-to-work law banning unions from requiring employees to join.

Some Republicans who remain optimistic about Earle-Sears candidacy argue skeptics had similar critiques four years ago when current Gov. Glenn Youngkin was trailing then-Democratic nominee Terry McAuliffe two months before the election. Youngkin eventually won the state by 63,000 votes and was seen as a sign of the GOP’s comeback after losing the White House and the U.S. Senate in 2020.

Earle-Sears, a Jamaican American woman running alongside an openly gay man for her lieutenant governor seat and the son of a Cuban refugee for attorney general, also represents an opportunity for Republicans to emphasize diverse credentials.

“It sounds like a Democratic ticket, right?’” said former U.S. Rep. Tom Davis, a Republican from Northern Virginia. “That’s the Republican ticket.”

“Look, there’s always grumbling,” said Katie Gorka, chair of the Fairfax Republicans, who attributes Earle-Sears’ fundraising earlier in the cycle to being hamstrung by her duties presiding over the state Senate and the Virginia legislature not wrapping its 2025 session until late February. Spanberger, no longer in elected office, could raise money for her campaign full time. So far, Spanberger has a big advantage: she raised $16.3 million in the first quarter compared with Earle-Sears’ $5.6 million, according to campaign finance reports.

Gorka, the wife of top Trump aide Sebastian Gorka, also dismissed assertions that the lieutenant governor made a blunder when comparing slavery to DEI programs in a fundraising blast.

“I think a part of her strategy is to make sure she reaches across the aisle and reaches a wide range of Virginians,” Gorka said. “Her talk about slavery and DEI might not appeal to the Republican base, but I think there are a lot of people who do respond to that.”

Still, many Republicans don’t feel the lieutenant governor is positioning herself well for the general election. Unlike Youngkin four years ago, Earle-Sears did not face a drawn out primary. The governor, who according to Virginia law is barred from serving consecutive terms, effectively cleared the field for her when Miyares decided to seek reelection instead of running for governor.

The lack of a competitive primary means that Earle-Sears has more work to do to introduce herself to Virginians, multiple Republicans said.

“I don’t think the average voter knows there’s a campaign on either side right now, to be honest,” Davis, the Northern Virginia Republican, said. “We used to say voters aren’t stupid, they’re just not informed. This will come down as: Are they comfortable with the direction of the state, and how much does the national bleed over into this?”