'I Look Like the Strategy': Winsome Sears Wants Black Voters to Rethink the GOP

Winsome Sears, Virginia’s lieutenant governor-elect, preparing to preside over a session of the Virginia State Senate at the capitol in Richmond. (Sarahbeth Maney/The New York Times)
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  • Winsome Sears
    American politician in Virginia (born 1964)

RICHMOND, Va. — On a December afternoon, Winsome Sears, Virginia’s lieutenant governor-elect, stood at the podium in the state Senate chamber where she will soon preside. It was empty but for a few clerks and staffers who were walking her through a practice session, making pretend motions and points of order. Sears followed along as the clerks explained arcane Senate protocols, although she occasionally raised matters that weren’t in the script.

“What if they’re making a ruckus?” Sears asked her tutors.

Then, a clerk said, pointing to the giant wooden gavel at Sears’ right hand, you bang that. Sears smiled.

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That she was standing here at all was an improbability built upon unlikelihoods. Her campaign was a long shot, late in starting, skimpily funded and repeatedly overhauled. The political trajectory that preceded it was hardly more auspicious: She appeared on the scene 20 years ago, winning a legislative seat in an upset, but after one term and a quixotic bid for Congress, she disappeared from electoral politics. She briefly surfaced in 2018, announcing a write-in protest against Virginia’s Republican nominee for U.S. Senate, but this earned her little beyond a few curious mentions in the press.

Yet, just three years later, she is the lieutenant governor-elect, having bested two veteran lawmakers for the Republican nomination and become the first Black woman elected to statewide office in Virginia history. She will take office Jan. 15, along with Gov.-elect Glenn Youngkin.

The focus on Sears’ triumph, in news profiles and in the post-election crowing of conservative pundits, has been on the rare combination of her biography and politics: a Black woman, an immigrant and an emphatically conservative, Trump-boosting Republican.

“The message is important,” Sears, 57, said over a lunch of Jamaican oxtail with her transition team at a restaurant near the state Capitol. “But the messenger is equally important.”

This is the question that Sears embodies: whether she is a singular figure who won a surprise victory or the vanguard of a major political realignment, dissolving longtime realities of race and partisan identification. Democrats say there is little evidence for the latter, and that Sears won with typical Republican voters in an especially Republican year. But Sears insists that many Black and immigrant voters naturally side with Republicans on a variety of issues — and that some are starting to realize that.

“The only way to change things is to win elections,” she said. “And who better to help make that change but me? I look like the strategy.”

Sears dates her own partisan epiphany to her early 20s. She already had plenty of life experience by that point: moving at the age of 6 from Jamaica to the New York City borough of the Bronx to be with her father, who had come seeking work; joining the Marines as a lost teenager and learning to be a diesel mechanic; becoming a single mother at 21. When she listened to the 1988 presidential campaign, hearing the debates over abortion and welfare, she realized, to her surprise, that she was a Republican.

More than a dozen years passed before Sears, then a married mother of three who had run a homeless shelter and gone to graduate school, began her political career. At the urging of local Republicans, she ran in 2001 for the House of Delegates in a majority Black district in Norfolk. The seat had been held by Billy Robinson Jr., a Democrat, for 20 years; his father had held it before him. Weeks before the election, Robinson spent a night in jail on a contempt-of-court charge. Sears won in the surprise of the election season.

In the Legislature, she adjusted to the political architecture and her unusual place in it: joining, then leaving, the legislative Black caucus; voting dependably as a Republican but calling earlier than many colleagues for the resignation of the Republican House speaker when news broke of his sexual harassment settlement.

She did not run for reelection, instead launching an underdog campaign against Democratic U.S. Rep. Bobby Scott. Scott returned to Congress, where he remains, and the House of Delegates seat returned to Democratic hands for good. Sears was “done with politics,” she said.

Her family moved to Winchester, a small city in the Shenandoah Valley, where Sears and her husband ran a plumbing and electrical repair shop. She held a few posts — on the state board of education and on a committee at the Department of Veterans Affairs — and wrote a book, “Stop Being a Christian Wimp!” Much of her focus was on caring for a daughter struggling with mental illness. In 2012, the daughter, DeJon Williams, was killed in a car accident along with her two young children.

While Sears was absent from politics, Barack Obama won the presidency, Trayvon Martin was killed, the Black Lives Matter movement rose up, Donald Trump was elected and neo-Nazis marched on Charlottesville, Virginia. Sears' political example, as a Black woman Republican representing a majority Black district in Virginia, went unrepeated.

Republicans, she said, rarely even tried to sever the old ties between Black voters and the Democratic Party. This is partly why she decided to run this year.

“I just took a look at the field, and said, ‘My God, we’re gonna lose again,’” she said. “Nobody was going to reach out to the various communities that needed to be heard from: women, immigrants, you know, Latinos, Asians, Blacks, etc.”

She stood to the right of much of the field and was arguably the furthest right of the three Republicans nominated for statewide office. She favors strict limits on abortion, calling Democratic abortion policies “wicked”; she is an advocate of vouchers to help students pay for private school tuition and of tighter restrictions on voting; and she insists that gun control laws do not deter crime — gun ownership does. A photo that went viral last spring, showing her holding an AR-15 while wearing a blazer-and-dress outfit suitable for a chamber of commerce luncheon, propelled her as much as anything to the Republican nomination.

Sears derides the left as too concerned with race but often explains her politics as rooted in Black history, stressing Marcus Garvey’s rhetoric on self-reliance as a Jamaican immigrant in Jim Crow America, emphasizing that Harriet Tubman carried a gun and referring to the infamous Tuskegee experiments in explaining her opposition to COVID-19 vaccine mandates. “If the Democrats are always going to talk about race, then let’s talk about it,” she said.

She rejects the notion that the problems Republicans have attracting Black voters might run deeper than mere neglect. She was angered when Republicans nominated Corey Stewart, who had a history of associating with neo-Confederates, for the 2018 U.S. Senate race in Virginia. But she said this didn’t give her qualms about the party. She remains a champion of Trump, who openly endorsed Stewart; indeed, she was the national chair of a group called Black Americans to Reelect the President.

Jennifer McClellan, a Democratic state senator from Richmond, agreed that Democrats could not assume that Black people would show up for them at the polls, saying that Black voters, like any voters, choose candidates based on who they believe is going to help solve their problems. But, she continued, little that Sears has said suggests she would be that person in office.

“The vast majority of Black voters disagree with her on abortion, on school choice, on guns,” McClellan said. “Those aren’t necessarily the issues driving Black voters anyway. It’s the economy, it’s health care, it’s broader access to education.”

The evidence that this year’s elections scrambled the fundamentals of race and partisanship is mixed at most. If anything, some Republicans worried that Sears’ hard-right politics might jeopardize the campaign strategy of appealing to more moderate voters. This risk was largely mitigated, said John Fredericks, a conservative radio host, by the fact that Sears’ general election campaign, which he called “a train wreck from start to finish,” never raised enough money to really broadcast her politics.

In any case, the attention was overwhelmingly directed to the top of the ticket.

“The election this year was all about the gubernatorial candidates,” said Stephen Farnsworth, a political scientist at the University of Mary Washington. There were few big surprises in the exit polls, several political experts said, and Sears won her race by a margin that would have been expected of just about any Republican this year.

But there were some warning signs for Democrats, outlined in a post-election survey by the Democratic Governors Association. Although Black Virginians overwhelmingly voted for Terry McAuliffe, the Democratic nominee for governor, the analysis found a drop in Democratic support among Black men, compared with the 2020 presidential election. There was notable erosion in Democratic support among Asian and Latino voters as well.

“We don’t need to be tied or beholden to one particular party,” said Wes Bellamy, a Black political activist and a former vice mayor of Charlottesville. He will be watching Sears closely, he said.

Lieutenant governors in Virginia are fairly limited in their responsibilities, but they have a public profile — and they almost always run for governor. If Sears advocates for policies that improve the day-to-day lives of Black people and, more crucially, if she can persuade her Republican colleagues to go along, Bellamy said, “I think she’s gold.”

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