Republican Lt. Gov.-elect Winsome Sears speaks during a GOP rally at Eagles Nest Rockin’ Country Bar in Chesapeake, Va., June 5, 2021. (Parker Michels-Boyce/ For the Virginia Mercury)
Winsome Sears made a political career of confounding people who told her she couldn’t do something; of zigging when conventional wisdom dictated that she zag.
A Black, conservative, evangelical Republican woman and former Marine, she was told she had no business taking on an entrenched Democratic House of Delegates member from a deep blue Norfolk inner city district.
She did anyway. And she won.
She was a crown jewel of the GOP after that, and the party touted her as a shining example of a big-tent party whose message of free enterprise and individual responsibility resonated as well in urban areas as in the backwoods.
And just as abruptly as she stormed on the scene, she was gone, inexplicably opting not to seek a second two-year term.
She resurfaced later to take on a Democratic titan, U.S. Rep. Bobby Scott, D-Newport News, but this time to disappointing results.
Then she faded from view again, retreating with her husband, Terence, to the Shenandoah Valley to work through some compelling problems confronting her family.
A year ago, she had the temerity to jump into the deep end of statewide politics with no money or organization and seek the office a heartbeat away from the Executive Mansion. The co-owner of a family plumbing and electrical business near Winchester competed for the nomination against Republican men who had elbowed into contention for the springboard office over many years in the General Assembly.
“I just saw a need, just like before,” she said in an interview last week, referencing her improbable 2001 House victory. “I just had a call and I knew I had to answer it.”
Nobody gave her much thought, much less a serious chance to win the nomination.
Until she did.
As 2021 wore on, even with polls showing steadily increasing support for Glenn Youngkin at the top of her party’s ticket, there was little belief among the political cognoscenti that a staunchly pro-gun, anti-abortion woman with an unabashed record as a supporter and fundraiser for former President Donald Trump could breach the Great Suburban Blue Wall that had buttressed Democratic victories in every statewide contest for a decade.
Until she did.
Now, the question is how the sometimes outspoken, unpredictable and impetuous hero of the Republican right will perform the largely ministerial, ceremonial and rote duties of presiding over a Senate still controlled by the adversary party.
The fact is, the 57-year-old Jamaican-born, Bronx-raised Sears does what she wants, and Republicans and Democrats alike have learned the hard way that when she makes her mind up, it’s nearly impossible to change it.
I’ve known that since I first interviewed her in 2001 for an Associated Press profile on her longshot race – her first bid for elective office – against William P. “Billy” Robinson, a legendary Norfolk criminal defense lawyer who had served in the House of Delegates for 20 years.
We met on a chill November night for a nearly two-hour conversation starting well after the dinner hour rush in a nearly empty McDonald’s in a Norfolk neighborhood that had seen better days. She had just concluded months of going door to door, business to business and church to church in a one-woman insurgency that she singlehandedly willed to victory in the heavily Democratic district.
This May, remembering that meeting and many conversations since, I was not surprised that she emerged the victor in a six-candidate Republican state convention field of lieutenant governor candidates, though I would not have predicted it.
Winning in November, however, seemed less probable. (I stress seemed.) At the top of the ticket, Glenn Youngkin was doing a delicate highwire act balancing fealty to Trump with keeping a safe distance from the divisive ex-president who had doomed numerous Virginia Republican candidacies. Sears, meanwhile, made no bones about her support for Trump. In 2020, she led a national organization dedicated to turning out the Black vote for him.
She embraced hot-button issues that Youngkin had gingerly circumnavigated, including repealing gun control laws the all-Democratic General Assembly enacted since 2019. She has praised a Texas law that effectively shut down abortion access there by giving private individuals who normally would lack legal standing a private right of action to sue abortion providers or anyone else – from a guidance counselor to an Uber driver – who even marginally helps a woman abort a pregnancy.
Conventional wisdom dictates those positions are non-starters for the generally college-educated, affluent, moderate voters in the suburbs of northern Virginia, Hampton Roads and the Richmond area who had powered one Democratic sweep after another since 2009.
Did she backpedal? Did she recant or relent?
No. And she won anyway, becoming the first woman of color ever elected to statewide office in Virginia.
So if you see her say cringeworthy things while mixing it up with cable news anchors regarding COVID-19 vaccines, critical race theory, the infrastructure bill and whether she’s been vaccinated (she won’t say), understand that she’s feeling confident in a way that only someone who’s taken your best shot and remains unfazed and standing can.
But will that same style serve her well once she is sworn in six weeks hence?
The first – and, until Jan. 15, the only – Republican ever to preside over a Democratic Virginia Senate is former Lt. Gov. Bill Bolling, who now teaches political science and government at George Mason University and Virginia Commonwealth University.
Most of the job, he recalled, is clerical and mind-numbingly repetitive. The action on the floor is largely out of the LG’s hands, controlled by the senators and majority and minority party leaders. The daily task is to keep order, oversee the roll call of floor votes and recognize members to speak. Once in a blue moon, the LG will be called upon to rule on the germaneness of an amendment to a bill, a determination that the floor can vote to overrule. Other than standing ready to ascend to the state’s highest office upon the governor’s death, resignation or disability, the highlight of the job is to break tied floor votes, something that has, in a few rare cases, determined the course of state law.
What it’s not, Bolling cautioned, is a place to pick partisan fights should one be so inclined.
“You can’t just do whatever you want,” he said. “To be credible in the role, you have to be very fair and objective in the rulings that you make because if you just start making rulings based clearly on politics, you’ll lose credibility really fast.
“You may be able to get away with that if your party controls the Senate, but if the other party controls the Senate, they’ll smack you down real quick by challenging the ruling of the chair,” he said.
That could put pressure on Sears, Bolling said. Youngkin will expect her to help shepherd his conservative legislative agenda through a Democratic Senate. She also needs to keep her hardline GOP base happy for a possible gubernatorial run in four years when Virginia’s unique, non-consecutive gubernatorial term precludes Youngkin’s re-election.
She faces a learning curve, too. The rules of the House that she may recall from her two years there are different from those of the Senate.
“The part of it that works for me is that I already know what ‘engrossed’ means. I already know what the third reading is. I already know what the calendar is,” Sears said. “As with anything I have ever done, I will have to learn, and this will be no different.”
With Winsome Sears, you get something of a wild card, even in her dealings with her own party at times.
In 2018, she jumped into the U.S. Senate race as a write-in candidate to take votes from Republican nominee Corey Stewart for associating with White supremacists. As a freshman House member in 2002, she was among the earliest Republican women delegates to call out Virginia’s first GOP House speaker, S. Vance Wilkins, after a Washington Post report that he had paid a woman to stay silent about an alleged sexual assault. A year later, Sears abandoned her seat, which the Democrats promptly reclaimed.
She’s one tough, confident woman, and it’s important to understand that neither side is going to dominate her. Attempting it wouldn’t end well. But, she noted, differences need not be permanent or intractable.
“I am a fighter, and I don’t let anybody walk all over me,” she said, “but that doesn’t mean you have to leave a bloody battlefield.”
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