The last time Winsome Sears was in Virginia’s political spotlight was 20 years ago, when she had defeated a powerful Democratic state delegate in Norfolk to become the first Black woman in the Republican Party to join the General Assembly.
Then, almost as soon as she showed up, Sears faded into relative obscurity as she retreated to tend to her ailing daughter, whose mental health battles ended in a family tragedy.
Now, Sears, 57, is back as the Republican nominee for lieutenant governor, facing Democrat Del. Hala Ayala of Prince William in a November election that will make one of them the first woman of color to hold a statewide office in Virginia.
Sears is hoping her story – that of a Jamaican-born ex-Marine whose deep Christian faith has pulled her through hard times – can energize the Republican base while winning over independent voters who will play a vital role in the increasingly tight statewide elections.
Political analysts say her value to a GOP ticket led by Glenn Youngkin, the party’s nominee for governor, will depend on how successfully Democrats can highlight another side to Sears: a Trump loyalist who supports a controversial Texas ban on most abortions and whose most prominent campaign ad showed her gripping an assault rifle.
“She won the nomination in part because she was able to appeal to the most conservative base in the Republican Party,” said Bob Holsworth, a longtime analyst of Virginia politics. “But her positions by and large are: pro-life, Second Amendment, school choice and ballot integrity. None of those issues are necessarily winners in a statewide race right now.”
Sears was widely dismissed in 2001 when she set out as a political novice to defeat former delegate William P. “Billy” Robinson Jr., D-Norfolk, a 10-term incumbent whose father had also represented the largely African American and historically Democratic House district in Norfolk.
By then, Sears – a mother of three daughters and director of a local homeless shelter – had developed an up-from-your-bootstraps worldview that includes her conviction that African Americans have been coddled too much by government programs.
“In Jamaica, we know that Black people can be anything they want to be,” Sears said in an interview. She recounted a childhood where, after immigrating to the United States with her father, she was sent back to the Caribbean nation for elementary school every fall because its public school curriculum was more rigorous than what she was getting in the Bronx section of New York.
She walked the Norfolk district’s impoverished neighborhoods and mined voters’ frustrations with their delegate, promising to help make it easier to send their kids to private or charter schools through publicly funded vouchers.
Robinson’s supporters took notice. One of them, a local leader of the New Black Panther Party for Self-Defense, regularly harassed Sears – enough to convince a general district court judge to order him to keep his distance.
“They told me to go home,” Sears said about her detractors. “I just pressed on and knocked on door after door.”
– – –
The Republican Party’s grip on the General Assembly in the early 2000s made success as a legislator easier.
A 2002 law Sears sponsored loosened state restrictions on charter schools, and another the following year made it easier for medical professionals to be disciplined for negligence.
But Sears displayed an independence that could put her at odds with her party’s leadership.
When news broke in 2002 that veteran House Speaker S. Vance Wilkins Jr. paid $100,000 to settle a sexual harassment claim against him, many Republicans cautioned against early judgment. But Sears spoke out.
“I might as well say it: If it’s true, then I think the Speaker ought to resign,” the rookie lawmaker told reporters.
Wilkins did step down about a week later. But any grudge held against Sears has long since vanished. The former House leader was an early supporter of her campaign this year, calling Sears “fearless, optimistic and charismatic” in an April endorsement.
Former Republican governor Robert McDonnell, who was a member of the House leadership during the early 2000s, said in an interview that Sears commanded respect from her colleagues.
“We thought this woman was going to make a difference on our side of the aisle for a very long time,” said McDonnell, who, like Sears, attended Regent University in Virginia Beach. Sears has a master’s degree in organizational leadership from the Christian-focused school.
McDonnell tapped Sears to take the lead on the most consequential bill of her legislative career: a 2002 ban on Ku Klux Klan-style cross burnings in Virginia.
An older ban on the racist intimidation tactic had been ruled unconstitutional by the state Supreme Court the previous year on the grounds that cross burning was protected as a form of religious expression.
Sears carried a bill that got around the decision by making it illegal to burn any object – including crosses – on someone else’s property.
Though there was nearly unanimous support in the General Assembly, the ban – which survived a U.S. Supreme Court challenge – allowed Sears to champion a visceral issue for African Americans, giving her more prominence.
– – –
Then, just as soon as she arrived, she left electoral politics.
The reason was related to her eldest daughter, DeJon Williams.
Sears said Williams, who was then 18, had begun behaving erratically and was later diagnosed with bipolar disorder.
Sears and her husband, Terence Sears, Williams’s stepfather, agreed a move to the partly rural Winchester area in the Shenandoah Valley would be therapeutic.
But Sears stuck around southeastern Virginia long enough to challenge Rep. Robert C. “Bobby” Scott, another veteran Democratic lawmaker, in 2003.
She lost, getting just 30% of the vote.
Sears receded into a life outside Winchester, helping to raise Williams’s two daughters – Victoria and Faith – while running a plumbing and electrical repair business she started with her husband.
In between, Sears wrote “Stop Being a Christian Wimp!” a religious-themed motivational book she self-published in 2009 about how to avoid being consumed by doubt and uncertainty.
She was a recently installed member of the state board of education – appointed by then-governor McDonnell in 2011 – when she had to follow her own advice.
The first ripple of trouble came from her granddaughter Faith, then 5, who happily informed Sears that “Jesus is going to give us a big house. A really big house.”
In the following days, the child kept saying that and began drawing pictures of big houses. Sears, confused, confronted Williams.
“Are you moving?” she asked.
Williams calmly replied: “I don’t know what she’s talking about.”
Sears said she didn’t realize then that her granddaughter’s “big house” was a misunderstood reference to a biblical passage about heaven, in which Jesus promises his followers: “In my Father’s house are many mansions.”
She also didn’t know that Williams had stopped taking her prescribed medication.
Soon after, Williams drove with her daughters at what police described as “an excessive rate of speed” along the Fairfax County portion of Lee Highway. Her car sideswiped another vehicle, causing a multiple vehicle collision.
Williams died immediately. Faith and Victoria, 7, died that night at a hospital.
Sears heard a knock on her door at 3 a.m., when a pair of police officers told her the news.
“You collapse; that’s what you do,” she said, briefly tearing up at the memory. “I just remember walking away from the door and dropping in the chair that was there and saying: ‘The Lord giveth and the Lord taketh. Blessed be the name of the Lord.’ That’s what I remember saying.”
– – –
Her reentry into Virginia’s political scene was gradual, but with high ambitions.
There was a 2018 write-in campaign for the U.S. Senate. And, last year, Sears chaired a national committee dedicated to turning out the Black vote for President Donald Trump.
Her bid for the GOP nomination for lieutenant governor was initially considered a long shot.
A spontaneous stop at a shooting range in Fauquier County in between campaign stops in April helped turn that around.
Sears and her then-campaign spokesman thought the range would be a good place to underscore her commitment to gun owners’ rights – a key issue among conservative Republicans who would determine the outcome of the party’s May convention.
Photos posted to social media showed Sears taking aim at a distant target with an assault rifle, her elbow propped against a bench for support.
She had slipped on an old green blazer from her days in the House to keep her polka dot skirt and white blouse from getting dirty.
The photo that ricocheted around social media and became a signature image for Sears’s campaign showed her posing with the rifle in the same outfit, her expression neutral, looking into the camera.
The point of the picture, she said, was to show that it isn’t just the typical White male who deeply cares about gun rights. People of color, including women, also hunt or own guns for protection, she said.
“A Black woman with a gun is a very powerful statement,” Sears said.
Her supporters say that instinct will help Sears win over independent voters who are likely to have a decisive impact on the elections.
Sears jumps at opportunities to show she arrives to her conservative positions from the perspective of a Black immigrant – someone who believes in standing up against racism, but doesn’t believe it’s systemic and doesn’t believe it requires subscribing to liberal government policies.
It’s why Sears called for an investigation into a case in Windsor where a Black U.S. Army lieutenant was pepper sprayed during a traffic stop, and why she repeatedly vows to push for the state to fully fund historically Black colleges and universities.
That perspective is also why she launched her Senate write-in campaign. The bid Sears said, was meant to undermine Corey Stewart – the GOP’s nominee to defeat Sen. Tim Kaine, D-Va., that year – over his having consorted with white supremacists while members of Stewart’s campaign made racist comments on social media.
“He was the wrong messenger,” Sears said about Stewart.
On the flip side, Sears has joined other conservatives in railing against critical race theory instruction in public schools. A tool for examining systemic racism, the teaching method is not used in Virginia schools but has become shorthand among conservatives for any effort to include a broader cultural context in classrooms.
“It’s supposedly to help someone who looks like me and I’m sick of it,” Sears told Fox News. “I’m sick of being used by the Democrats and so are many people who look like me.”
Democrats say such talk is part of a far right-wing tendency in Sears.
Ayala uses the image of Sears holding the assault rifle in her campaign ads, which call the Republican “too radical” and “too dangerous” for Virginia.
Ayala has also attacked Sears over her support for a Texas law that bans most abortions after six weeks and for her refusal to say whether she’s been vaccinated for the coronavirus.
Other Democrats note how Sears has called for voter ID requirements in Virginia elections, part of the outgrowth from the false belief among Trump supporters that the presidential election was stolen.
Sears has never publicly questioned the outcome of the election and expressed dismay at the Jan. 6 riot at the U.S. Capitol that resulted in five deaths.
“Folks, this is not the way to fight,” she tweeted that evening.
But political analysts say Sears’s continued loyalty to Trump is enough to turn off many voters in a state where the former president remains deeply unpopular. In what may be a nod to that reality, Sears recently ducked out of a Richmond-area rally headlined by Trump – who called in – before she was scheduled to speak, offering no explanation.
Sears is banking on any uneasiness moderate voters might feel over Virginia’s direction in recent years, calling Ayala part of a cadre of “liberal elites” in the General Assembly who recently abolished the death penalty and made it legal for adults to possess small amounts of marijuana.
She sees herself as the answer in a more diverse Virginia to the GOP’s string of defeats in statewide races since McDonnell was elected governor in 2009.
“We’re hitting a wall,” Sears said, about those losses. “So, we’re going to get the new customers and they’re in the Democratic Party. They don’t know yet that they’re conservative. I’ve won with that strategy.”
Pausing, she added: “I look like that strategy.”
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