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Will Winsome Earle-Sears become the first Black woman governor?

How race and identity are shaping politics, policy and power.
Sep 08, 2023 View in browser
 
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By Brakkton Booker

With help from Emma Creamer, Jesse Naranjo, Rishika Dugyala and Teresa Wiltz 

Photo illustration depicts cutout of Winsome Earl-Sears smiling over torn-paper background.

POLITICO illustration/Photo by AP

What up, Recast family! Fulton County District Attorney Fani Willis claps back at House Judiciary Chair Jim Jordan (R-Ohio), who is investigating her office following Trump’s latest indictment. And a new report finds Trump’s border wall caused “significant” cultural and environmental damage. First, a chat with a woman who could be Virginia’s next governor.  

Lt. Gov. Winsome Earle-Sears does not shy away from the history she made two years ago when she was elected as the first woman of color and first immigrant in statewide office in Virginia history.

Nor does she let it define her.

She views her role as inspirational, but says her achievement does not mean she is taking on the added role of helping the party reach Black voters — especially Black women, who are Democrats’ most loyal voting bloc.

During the last presidential cycle, the Kingston, Jamaica-born Earle-Sears served as national chair for Black Americans to Re-Elect President Trump. Since then, she’s become increasingly critical of the hold the former president has on the GOP.

Following the party’s poor performance in last year’s midterms, she publicly broke with the ex-president after a string of far-right, Trump-endorsed candidates lost. She signaled her displeasure in a way that perhaps only a former Marine would: “A true leader understands when they have become a liability. A true leader understands that it’s time to step off the stage.”

Trump hit back, calling her a “phony.”


 

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Last month, her memoir, “How Sweet It Is: Defining the American Dream,” was released, chronicling her unique rise in American politics. It came out just as rumors began swirling about her political future if her boss, Republican Gov. Glenn Youngkin, decides to challenge Trump for the GOP nomination.

Youngkin, who has said publicly he is not interested in running, is being encouraged to jump in as a dark horse candidate by GOP boosters who have soured on Trump, including media mogul Rupert Murdoch.

Should Youngkin change his mind — and win — that could leave an opening for Earle-Sears to become the nation’s first Black woman governor. Even if none of this comes to pass, because Virginia’s law prohibits governors from serving consecutive elected terms, she could seek the top job herself in 2025.

Earle-Sears, for her part, says she is focused on the task at hand.

◆◆◆

This interview has been edited for length and clarity.

THE RECAST: I’m curious about your path to conservatism. You write in your book that you had a sort of aha moment, during the presidential election of 1988.

EARLE-SEARS: [George] Bush, the father.

THE RECAST: You write that you were no fan of Ronald Reagan. And you go on to write: “I’d never voted at that point, but I figured, well I’m Black. I’m supposed to be Democrat. Who told me? Nobody and everybody.”

Could you talk about how you realized you were Republican at that point in time?

EARLE-SEARS: So I can’t really say that my family were Democrats — I really don’t know what they were.

I know we talked politics all the time — we just always had point-counterpoint, you know? So I think more than anything they were independents, because in Jamaica, Black people are on both sides of the political spectrum.

Winsome Earle-Sears speaks into a microphone with a finger pointed upward.

Earle-Sears addresses the Virginia FREE Leadership Luncheon on Sept. 1, 2021, in McLean, Va. | Cliff Owen/AP Photo

But I think more than anything, the second generation will assimilate. I was still the kid who came off the Pan American plane, I was growing up as a youngster in America and took on Americanisms. And around me, Black people are Democrats. And I guess that's what [I thought] I'm supposed to be.

It wasn't until I had had my first daughter, and my last child, really, that I heard a message I had never heard before. Following an ad for [Democratic nominee] Michael Dukakis, I thought, “Well … I don’t believe any of those things he’s talking about.” And then I heard Bush, the father, saying things like: “I'm going to ensure that abortions that are rare — safe and rare.”

And then the thing he said that blew my mind was this: “If all you ever have is welfare, you will never have anything to pass on to your children.” And it was then I said to myself, “Oh my God, I am a Republican.”

THE RECAST: And now you’re the first Black woman to serve as lieutenant governor of your state.

EARLE-SEARS: First female Black or white or anything.

THE RECAST: Do you feel like you have a special role in the party as someone who can speak directly to Black women about conservatism? Do you feel like the Republican Party is doing enough to reach out to Black women?

EARLE-SEARS: I'd say so. And it's not my job to do it, either.

Winsome Earle-Sears raises her hand during oath of office ceremony surrounded by family and other officials.

Earle-Sears takes the oath of office during an inauguration ceremony, Saturday, Jan. 15, 2022, in Richmond, Va. | Julio Cortez/AP Photo

It used to be that we would think, “Well, Black people will never vote Republican, it's going to take too much money, and too many years to try to change those minds.” And so maybe we went after other voters.

I think we're opening up places, in communities for all stripes and colors and backgrounds and socioeconomic situations. And that's how you should be; you should market yourself to everyone.

I play different roles for different groups of people.

I think when immigrants look at me, they say to themselves, “Well, if she can do it, why can't I be lieutenant governor?”

I remember this one young woman [visiting in the Senate gallery who] sort of elbowed her daughter and pointed down at me to say, “You see her, you can be her too.” She was Asian!

And when I talk to, especially young Black girls, I say to them, “You can do something that I can't: You can be president of the United States.”

Quote from Virginia Lt. Gov. Winsome Earle-Sears reads, "I play different roles for different groups of people. I think when immigrants look at me, they say to themselves, 'Well if she can do it, why can't I be lieutenant governor?'"

THE RECAST: There are a handful of districts in Virginia that are defying the state's newly adopted guidelines regarding transgender students in K-12 public schools.

Some of the bigger school districts have vowed not to adopt those guidelines. Are there tools in the administration’s toolkit that could make school districts comply with the state guidelines?

EARLE-SEARS: The governor is consulting with the attorney general.

In the meantime, I know that there are some parents who are considering suing. And I say, more power to them. Because listen, my child is my child. My child does not belong to the government. Enough parents are saying they don’t like what they’re seeing.

It’s not that they have anything against transgenders — it’s just that they don’t want their girl children to be driven off the victory spot on the podium because they’ve lost to a biological male who is stronger and faster than their daughter is.

I think we know that there is fairness in this. The governor has put forward model guidelines that say we will treat all children with respect, dignity, and we will treat all children with privacy. That means everybody must be treated with dignity, privacy and respect.

THE RECAST: You and Gov. Youngkin swept into office two years ago on the strength of a school choice message. And I know it is your hope and the party’s hope that Republicans will take back the state Senate this fall to secure a governing trifecta. Is there any concern that playing up this issue will backfire?

Glenn Youngkin gestures with his hands while speaking to Winsome Earle-Sears.

Then-candidate Glenn Youngkin speaks with Earle-Sears after a rally Oct. 30, 2021, in Fredericksburg, Va. | Steve Helber/AP Photo

EARLE-SEARS: No, because you see, we're hearing from our constituents, this is what they want. They want fairness in sports for their daughters.

We can't afford to play these games. Let's get back to the basics. What is the purpose of education? It is to give my child the ability to read and write and to teach them civics, etc. But leave the moral stuff to me, as the parent. I will make that decision.

THE RECAST: Gov. Youngkin’s name continues to be floated as someone who could jump into the Republican nominating contest for president. Should that happen, it presents the opportunity for you to be elevated to the governor's mansion.

Do you think he should enter the race?

EARLE-SEARS: Well, he's already stated that he is very much looking at and focusing on 2023.

We have to win the [state] Senate back. If we don't win the Senate, then it will mean he will have spent all four years of his term as governor with a hostile Senate that is determined to stop everything that we're trying to achieve.

And then of course, we have to keep the House. So that is his focus. And that is mine as well.

Winsome Earle-Sears stretches her arms wide while taking the stage in front of crowd.

Earle-Sears takes the stage during an election night rally Nov. 2, 2021, in Chantilly, Va. | Chip Somodevilla/Getty Images

THE RECAST: You’ve been critical about the party under Trump, certainly after last year’s midterms with Republicans underperforming.

Do you think Republicans need to move on from Trump?

EARLE-SEARS: Well, I'm gonna tell everyone to read my book and you’ll find more information there.

But here's what I know: In Virginia, we could not have won had we not had enough Democrats and enough independents who decided that we had a common sense approach to legislation, and how to govern. And so they jumped ship and voted for us.

It's the same in America herself. We’re politically split almost 50-50 with independents in between, and we're not going to win — we Republicans — in November of 2024 if we do not convince enough of a percentage of Democrats and independents to vote for our side.

So we have to nominate not just somebody who can win in the primary, but someone who can win in November of 2024. Because if you can only win the primary, we're going to be wringing our hands all over again saying, “What are we going to do?”

No, we can’t afford that. Too much is at stake.

Quote from Virginia Lt. Gov. Winsome Earle-Sears reads "we're not going to win —  we Republicans — in November of 2024 if we do not convince enough of a percentage of Democrats and independents to vote for our side."

THE RECAST: Some anchors on Fox News have floated this idea that Trump’s legal woes will somehow endear him to Black voters, the central argument being that a lot of Black folks see the criminal justice system as treating them unfairly and now Black voters will sympathize with what Trump is going through.

I’ve not seen evidence to support that point, but have you given this any thought?

EARLE-SEARS: You know, I really haven't heard that.

More than anything, what Black voters have begun to think is, “Wait a minute, that plea deal that Hunter Biden [initially] got, I couldn't have gotten that. My child couldn't have gotten that.”

You’re talking about treason, you're talking about working with a foreign adversary, you're talking about millions of dollars and even grandchildren who are underage or who are getting millions? Come on!

I don't have a crystal ball, but anything can change at the drop of a hat. But 2024 is a long way away.

THE RECAST: And so is 2026. You were coy about whether you had thought about whether Gov. Youngkin will jump into the presidential race. But one thing for sure is he is not running in two years. You’d take office in 2026 should you win. Have you given that any thought?

EARLE-SEARS: What I can tell you for sure: I am not running for president [chuckles].

◆◆◆

Sending you happy Friday vibes!  Here are some news items and weekend pick-me-ups! 

Yale Lawsuit Dropped — The Edward Blum-backed Students for Fair Admissions has dropped its lawsuit challenging Yale’s race-conscious admissions, reports POLITICO’s Bianca Quilantan.

Sending You a Nine-Page Letter — Fani Willis, the DA in Fulton County, sent a fiery response to Rep. Jim Jordan. POLITICO’s Jordain Carney breaks down what it all means.

Is Barbara Lee Fading? — POLITICO’s Alexander Nieves unpacks a new poll showing Rep. Barbara Lee trailing by double digits to fellow Democratic Reps. Adam Schiff and Katie Porter in the race to replace Dianne Feinstein.

Border wall construction "caused significant damage and destruction" to Native cultural sites, damaging parts of Monument Hill in Arizona and destroying a burial site in the Sonoran Desert near a sacred spring, GAO found.

Border wall construction "caused significant damage and destruction" to Native cultural sites, damaging parts of Monument Hill in Arizona, the Government Accountability Office found. | Joe Raedle/Getty Images

Trump’s Border Wall Bad for Culture, Environment — “The border wall championed by President Donald Trump harmed the environment and trampled on Native American cultural sites,” writes POLITICO’s Alex Guillén. 

Poet/activist/hip-Hop journalist Kevin Powell just released his new spoken word poetry album, “Grocery Shopping with My Mother.”

In “The Changeling,” LaKeith Stanfield plays Apollo, a book dealer who meets Emma, a librarian. Family life takes a dark turn…

YouTube thumbnail shows LaKeith Stanfield holding baby in video titled "The Changeling — Official Trailer | Apple TV+"

Zadie Smith's dazzling first historical novel, "The Fraud", is set between Britain and Jamaica and is inspired by a celebrated 19th-century court case.

Olivia Rodrigo drops a new album, “Guts,” packed with pop-rock, emo-adjacent, grunge-y tracks.

In the coming-of-age movie, “Aristotle and Dante Discover the Secrets of the Universe,” two Mexican American boys who meet in 1980s El Paso form an instant bond.

We’re here for the funky, jazzy vibes of synthesizer queen Hiromi’s energetic Tiny Desk concert.

YouTube thumbnail shows Hiromi leaning over keyboard in video titled "Hiromi: Tiny Desk Concert."

TikTok of the Day: So annoying!!

TikTok thumbnail shows claymation man sleeping in bed.

 

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