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In 2002, Winsome Sears was elected to a single term in Virginia’s House of Delegates. Now, two decades later, the pugnacious Republican is back and convinced she can help the GOP win a new coalition of commonwealth voters to help turn Virginia red.
On May 11, Sears, 57, was nominated by Virginia Republicans to be their candidate for lieutenant governor. She triumphed over five other opponents in a nominating convention that lasted five rounds. In the final round, she ultimately beat former Del. Tim Hugo of Fairfax County by a 9-percentage point margin. Sears joined gubernatorial nominee Glenn Youngkin and Jason Miyares, the nominee for attorney general, on Virginia’s GOP statewide slate.
Sears is a former Marine whose family emigrated to the United States from Jamaica in the early ’60s. And though she has been off the scene for a while, she is no stranger to Virginia politics. During an interview with the Washington Examiner, Sears explained that it was time for her to jump back into the game.
When she was elected in 2002, Sears was the first female veteran and the first black Republican woman to serve in the Virginia House of Delegates. In her first year, she carried a bill banning cross-burning in the commonwealth, aimed at groups such as the KKK. The Supreme Court, however, decided in 2003 that the statute was only constitutional in instances where there is evidence the intent was to intimidate others. The court also ruled that the portion of the law that treated any cross-burning as prima facie evidence of the intent to intimidate was unconstitutional.
“My second year, I took on the powerful medical establishment,” Sears told the Washington Examiner. “We were able to get rid of bad doctors and other bad things that were happening, even up to the funeral boards. We organized reforms targeting 13 different medically related boards.” It was then, in her second year, she explained, “when people said, ‘What she’s doing is committing political suicide.’ But nevertheless, I’ve been gone for 18 years.”
In 2004, she mounted an unsuccessful bid for Congress against incumbent Rep. Bobby Scott, a Democrat who has held the seat in Virginia’s 3rd Congressional District since 1993. Afterward, she went on to become vice president of the Virginia Board of Education and received presidential appointments to the U.S. Census Bureau and Department of Veterans Affairs.
The past 12 years of her life away from politics she spent in Winchester as the owner of a plumbing, electrical, and appliance-repair business. Over that span, Republicans' fortunes turned sour in Virginia's statewide races, and by 2018, the party lost control over both chambers of the General Assembly. The Old Dominion, which was previously a GOP powerhouse next door to the nation’s liberal capital, went all blue.
“I had won my last election 20 years ago, so just call me Moses. I came back after 20. Moses came back after 40, but I think I made the case to them,” Sears said of her return to politics and talking to voters. “It was time for us to start doing things differently. If [the GOP] needs new voters, then certainly, we’re going to need them in Virginia.”
Sears made history when she first won her Hampton Roads Assembly district two decades ago. Her victory in 2002 toppled Democratic incumbent William P. “Billy” Robinson Jr. from a seat he had held for 20 years and his father, William P. Robinson Sr., had held for a decade prior. “I had won my race. A black Republican in a 60% black district, which hadn’t happened since 1865,” she noted. “So, they figured we’re going to take a chance on her,” she said of Virginia party leaders this go-around.
Sears referenced recent statewide races Republicans lost in Virginia. These include Donald Trump’s loss to President Joe Biden in 2020, 44% to 54%; GOP Senate candidate Daniel Gade earning just 44% to Democratic incumbent Mark Warner’s 56%; and Republican Ken Cuccinelli’s 45% to Teri McAuliffe’s 48% in his 2013 run for governor.
“So, we’re hitting a wall,” Sears explained. “And those numbers I had mentioned would include, yes, libertarians, although they do occasionally run somebody,” which “did seem to factor in the Cuccinelli race, but, generally, they vote with us.”
“It definitely includes Republicans,” Sears continued, listing off the various coalitions that make up the GOP vote totals in the state. “It includes Tea Party Patriots and Republican-leaning independents.” But, she emphasized of the recent losses, “there’s nobody else.”
“So, where are they?” Sears asked. “They are in the Democratic Party, and they are conservative, and they don’t know it,” she explained. “I have a strategy to win those votes. In fact, I helped use that strategy to bring in voters who are not of this fold, and I worked with that strategy, and I look like the strategy.” She added: “So, we need to bring in Asian voters, Latino voters, and black voters. ... We can’t keep doing the same thing, expecting different results.”
The night Sears won her nomination, her most prominent campaign photo blared across Twitter. Wearing full makeup, a green blazer, a white knee-length skirt with black polka dots, and a white top, Sears holds a semi-automatic rifle across her chest with the muzzle pointing downward. Just above her name and the office she is running for read the words: “Battle Tested Conservative. Semper Fi.”
The scolding was immediate. Virginia Democratic Del. Mark Levine tweeted, “An assault weapon is not a toy. It shouldn't be used as a prop. Winsome Sears is glorifying gun violence. We need a Democratic nominee who can show Virginia how dangerous Winsome Sears is.” Virginia Democratic Del. Dan Helmer followed suit, calling it “abhorrent that you would try to score political points while kids are being killed with these weapons.”
According to Sears, the photo came about by happenstance. “I was actually on my way to one of my campaign events, and that’s why I'm so dressed [up]. So, it looks like I was going to church. Well, possibly, but I was on my way to a campaign event, and my campaign manager says, ‘Hey, why don’t we stop and shoot a few rounds?’” Sears agreed to the idea and said if you look closely at the photo, you can spot the ear protection she is wearing.
Touting her support for the Second Amendment, she referenced the early, racist gun control laws that kept firearms out of the hands of black people. “It was the Democrats. The Democrats did not want black people to own guns,” she said. “[Guns are] for our protection, and the fastest gun-owning segments [of the population] are black women.” Yet, she lamented, “the only time that black people are mentioned in the news, or you see black people with a gun anywhere in print, is in relation to a crime,” she said.
“We need to change that narrative. There are many legal, black gun owners. And we deserve our gun rights as much as anyone. So, I'm a Marine, and I'm in that photo.”
While the reaction to the photo from media talking heads and political opponents was negative, Sears says voters felt otherwise, and told her so on the campaign trail:
“More often than not, they love it. I was talking with someone the other day, and he’s a black Republican. He was telling me that his friend is a Democrat, and he said, ‘We’re gonna vote for Winsome.’
And the man said, ‘You mean the one with the gun?’ He said, ‘Yeah.’
‘Oh, yeah,’ the friend responded. ‘She’s got my vote. I love that gun.’”
Kerry Picket is a senior campaign reporter for the Washington Examiner.
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