Winsome Earle-Sears

“I’m telling you that what you are looking at is the American dream,” Winsome Earle Sears told the cheering crowd.  

“Winsome! Winsome! Winsome!” the crowd roared back.   

Earle-Sears was delivering her victory speech in the early morning hours of the day after the November election. The voters had spoken: Winsome Earle-Sears, Jamaica-born Republican, retired Marine, businesswoman, mother—and yes, embodiment of the American dream—would be Virginia’s new lieutenant governor. She is the first black woman to serve in this capacity.

And never let it be doubted that Earle-Sears can deliver an old-fashioned patriotic speech with the best of them. “When I joined the Marine Corps, I was still a Jamaican,” Earl-Sears recalled for her enthusiastic supporters that morning. “But this country had done so much for me, I was willing, willing, to die for this country.” After an upset victory, Sears and her running mate, Governor Glenn Youngkin, were sworn in at the Capitol in Richmond on January 22.

Earle-Sears, who won the hard-fought battle to run for lieutenant governor after five ballots, strikes fear into the hearts of Democrats. She is just the sort of dynamic, black politician in a high-visibility job who might inspire other African Americans to consider the Republican party. Earle-Sears herself had automatically assumed she was a Democrat. She is asked to tell the story about how she realized she was a Republican. “I’m not sure you have the time for that, but I’ll give you the quick version,” the Lieutenant Governor says, chuckling.

“Well,” she says, “we were living in California at the time. I had gotten out of the Marine Corps. My husband was still in the Marine Corps, and I had had my last child and she was about three months old. Anyway, this was around the time that George H. W. Bush was running for the presidency along with Michael Dukakis, as you know, in opposition. And Dukakis came on with his commercial, and he said he was going to expand abortion, et cetera, et cetera, and just raise taxes and everything else. And I thought well, heavens, I don’t believe in any of those things.

“I just assumed I was a Democrat because, well, I’m Black, I’m supposed to be that,” Republican Lt. Governor Winsome Earle-Sears recalls.

“And right behind Dukakis’s commercial,” she continues, “came George H. W. Bush’s commercial, and he said he was going to reduce abortions as much as possible. And I thought, well, that’s wonderful because you know, I just had my last child three months prior. And then he said he was going to reduce our taxes. And I thought, well, that’s excellent because I’m frugal. My kids tell me I’m cheap, but no, I’m frugal. And then the last thing Bush said absolutely blew my mind. And what he said was, ‘If all you ever have is welfare, you will never have anything to pass on to your children.’ And I thought to myself, oh my God, I’m a Republican. And that’s how I realized that I was a Republican because I heard a message I had not heard before and nobody had ever knocked on my door to talk to me about it, nobody had ever asked me my opinion.

“I just assumed I was a Democrat because, well, I’m Black, I’m supposed to be that. And that’s what we have to ensure—we must take our message to the people and have them make a decision for themselves. We don’t just assume that they’re not going to vote for the conservative position. No, that’s what the other side would like us to do. Just assume. And if your enemy, for lack of a better word, wants you to do a certain thing, then that’s what we’re not going to do, because we have to preserve America.”

Earle-Sears’ remarkable story begins in Kingston, Jamaica, where she was born Winsome Earle—Winsome is an English name, bestowed on the future lieutenant governor in honor of an Indian lady named Winsome, who was her mother’s best friend. At the age of six, Winsome came with her father to the United States. They settled in the Bronx, New York City.

When Earle-Sears’ daughter Dejon L’Air Williams and two grandchildren were killed in an automobile accident in 2012, the distraught mother turned to her faith.

Earle-Sears remains proud of her Jamaican heritage, especially of being a descendent of a legendary historical figure in the island’s history, Nanny of the Maroons. “The Maroons were African slaves, who never mixed with anyone else, and they came down from the mountains and threatened that they would burn the plantations and kill everybody, until the British decided to make a treaty with them. They were led by a woman, an African princess,” Earle-Sears says proudly, referring to Nanny of the Maroons.

Earl-Sears made an observation about the Bronx’s public school she attended: it wasn’t as good as her Jamaican schools. “I was spelling words like ‘this’ and ‘where,’ and [back in Jamaica] they were spelling ‘acknowledgment’ and ‘accomplishment’—and knew exactly what those words meant,” she recalled to the Wall Street Journal’s Tunku Varadarajan. Varadarajan calls this youthful epiphany Earle-Sears’ “first of her many revelations about black underachievement in the U.S., which have instilled in her a fierce contempt for an overly politicized educational establishment as well as an adamant belief in school choice.” And also, by the way, making Earle-Sears an ideal running mate for Governor Youngkin, whose campaign famously emphasized rigorous, depoliticized educational standards and parental rights.

Earle-Sears joined the Marines as a teenager. What prompted her to do this? “Well, I did it because my grandmother died,” replies Earle-Sears. “My grandmother died two months before I was supposed to start college. I had everything all in place, my books, everything all set, my curriculum, my courses, everything. And she died. And when she died, I thought my whole life was over. I went back to Jamaica, and I was going to stay there and die. And my mother said to me, ‘well if you’re going to stay here and die, then I’ve got some rules.’ You can’t do this, can’t do that, can’t, can’t, can’t. And I thought, ‘well, I’m going back to America.’

“Nobody tells me what to do in America. But I was just lost without my grandmother. My mother had on her table a Jet magazine. And I flipped it open and there was a picture of a Marine standing strong, the few, the proud, the Marines. And I thought, yes, the Marines will give me a reason to live. The Marines will give me the discipline I need. And so, I joined the Marines. And yes, I got the discipline all right.”

Earle-Sears worked as an electrician while in the Marines. She also acquired a husband, Terrence Sears, a fellow Marine. After Winsome and Terrence completed their Marine service, they eventually founded Shenandoah Appliance Plumbing & Electric in Winchester, Va. The couple had three daughters. Winsome worked in a bank, ran a Salvation Army homeless shelter, and enrolled as a graduate student in Regent University. Winsome was interested in politics but still saw herself more as somebody who ran a campaign rather than the candidate. At 37, however, in 2001, she ran for office and defeated a 20-year incumbent in the Virginia state House of Delegates. The Wall Street Journal’s John Fund called it a “Winsome v. Goliath” saga. Sears ran unsuccessfully for Virginia’s 3^rd congressional seat in Congress, and then, as suddenly as she had appeared on the political scene, Winsome Earle-Sears vanished from politics to help her daughter Dejon, who suffered from bipolar disorder.

Earle-Sears’ daughter, Dejon L’Air Williams, was only 27 when she and her two children were struck and killed in an automobile accident in 2012. The distraught mother turned to her faith. “It wasn’t just Dejon who went to heaven that day,” Sears recalls. “It was my two grandchildren as well. So, all three of them in one night. It’s—let me tell you, it’s nothing I’d ever wish on my worst enemy. But because I know that there is a God and I know that there is a heaven, I know that I shall see them again one day. And so, even though I was collapsing here and there, I would get up and understand, no, no, no they are quite fine. They are quite fine. And so that’s how I live my life. And there are people who would like me to be less vocal about my love for the Lord, but I’m not going to let them make me, because that’s what saved me.”

Earle-Sears’ faith led her to write a book with the rousing title “Stop Being a Christian Wimp!” It is a self-help book for Christians, bearing the subtitle “Don’t Let Worry, Doubt, and Fear Defeat You!” 

During her absence from elective office, Earle-Sears was a program manager for the Hampton Roads Chamber of Commerce and did volunteer work. She has served as Vice President of the Virginia State Board of Education; has been a presidential appointee to the U.S. Census Bureau, as co-chair of the African American Committee; and, served on the Advisory Committee on Women Veterans to the Secretary of Veterans Affairs. Encouraged by Terrence, however, Winsome began thinking about running for office again. She thought the country was in trouble, and she wanted to do something to help. “How can America remain a superpower without an education system that works?” she asks.

“We should remember,” the lieutenant governor continues, “that Rome wasn’t destroyed from without. Rome was destroyed from within. She destroyed herself. She did not fight her battles. There were no real borders. A country is nothing without borders. How do you define the country? We can’t be trying to secure Ukraine’s borders without securing ours. It makes no sense.” 

“Then when we look at businesses, and it’s almost as if we’re trying on purpose to destroy them with unnecessary regulations, tie their hands behind their backs. They can’t produce this, they can’t produce that. We don’t have the energy that we need because we’re running after green energy, which is fine, but you can’t cut your nose off to spite your face. You can’t, as Mr. Biden is doing, tell Saudi Arabia and the other OPEC countries that they should increase their oil output when the president has shut down our own potential to produce energy, when we were net exporters of oil, now we’re dependent on other countries. And so, decline is possible, if we don’t wake up. We wake up by voting differently. We wake up by holding those who want to lead us to account. We wake up by putting common sense back in our lives.”

Earle-Sears favors restoring rigorous learning standards and is a foe of Critical Race Theory, which presents American history as an unredeemable sequence of just one racist act after another. “Slavery happened, absolutely,” she told NPR. “And there are some vestiges of it. But how long are we going to go back there?”  

She has a message for her own party, too. “We’ve always had a chance of attracting more black voters, but we’ve let some of them—certain people in the party—destroy our brand,” she warns. “And we’ve always had to come back and apologize for them. You can’t tell me as a black person that you’re going to try to lynch me, for example, and think I’m going to vote for the party. We’ve got to get those kinds of people out. And they don’t represent us. They never represented us because the Republican Party was started for black people, to save black people from slavery.

“So, how could it be that the party that should be our natural home is not? Black people are by and large conservative. We just don’t vote that way and it’s because we don’t know Republicans. And by the way, we’re not trying to win the votes of all black people, because you’re not going to ever do that. We’re trying to win some of them because that’s just the way of the world. Same thing for Asians, same thing for Latinos, same thing for anybody.”

Earle-Sears is tough. She didn’t back down when a controversy erupted after she was pictured defending a campaign sign holding a rifle. The picture caused a lot of pearl clutching. “I am a Marine. I’m very comfortable with weapons, and, by the way, we do have a Second Amendment right to have these weapons. That is not an issue,” Sears said. Sears is also good at thinking on her feet. A friend had suggested I ask Sears how being an electrician played into her being a politician. It was a question out of left field, right? She said she’d never thought about it, but quickly managed to turn the topic into a little parable with larger implications.  

“I’ve never thought about it that way,” she began modestly enough, “but I do know that electricity will always seek the easiest path. It will. So, you know, it’s like water, water will sink to its lowest level. It’s what it does. So, the elements can tell us what to do and what not to do. We certainly don’t want to sink to our lowest level as water does. And we certainly don’t want to find the easiest path in life because that’s no way to live. We had a president who once said, ‘Ask not what your country can do for you, ask what you can do for your country.’ That’s not appreciated these days, because we’ve gotten into this mentality of me, me, me, me, me. We must never seek the easiest path or the lowest level.”

Since we are an organization for independent-minded women, it should be noted that Earle-Sears’ core staff in the lieutenant governor’s office is all-women. “I wouldn’t say it came about by accident,” Earle-Sears explains. “I would say that it came about as a result of interviews. I didn’t set out to have an all-female team, but it didn’t just happen that way. We interviewed quite a bit, quite a few people, men, and women. And this is the team that works together. This is the team—and it has to be a team—that is very secure in itself. These women are accomplished. For example, my chief of staff was recommended by two governors. She was recommended by other leaders. And most of these women have gone through some adversity that they have come out on the other side stronger.”

IWF wanted to know how Terrence likes being the Second Gentleman of Virginia. She replies, “The other day somebody said to him, how do you walk in your wife’s shadow? And he said I don’t. He has his own shadow. And by the way, it was his idea for me to return to political life after a long hiatus. He kept pushing me to get back in politics because he said he thought I had a job to do. I wasn’t certain I wanted to come back. He was the one who said no, you must go, you must go. So, he’s very secure in himself.” Terrence has retired several times and always comes back himself. He currently works for a car dealership.

Virginia’s governor is term-limited and many lieutenant governors have gone on to seek the top job. At 58 and with a growing national profile, Earle-Sears would be a natural candidate for governor. “Well, let’s see,” says Earle-Sears. “I have my children and this job, and it is called being Lieutenant Governor of Virginia. And so far, I’ve got three years and 10 months left. and I’m going to be the best lieutenant governor that I could possibly be. I’ll think about that another time.”

Not that we have anybody in particular in mind, but a lieutenant governor ascends to the top job if the governor gets a more important job. Whatever the future holds, we’re probably not going to see Winsome Sears take another hiatus from politics. The lady has a future.