One of these women will make history in Virginia on Election Day

Posted at 4:30 PM, Nov 01, 2021
and last updated 2021-11-02 10:15:06-04

RICHMOND, Va. -- In 2001, Republican Winsome Sears pulled off a major upset in Norfolk when she unseated the Democratic incumbent Delegate Billy Robinson. Robinson had been in power for 20 years.

"He was an icon," former Delegate Thelma Drake said.

Sears became the first black Republican woman to serve in the Virginia House of Delegates.

The win helped Republicans, including Sears' mentor, Drake, increase their majority in the General Assembly.

"Worked very closely with her during that campaign, and was very excited and happy to see what she was able to do, really almost a miracle," Drake said.

Sixteen years later, another remarkable upset, this one in Prince William County, where Democrat Hala Ayala toppled four-time Republican incumbent Delegate Rich Anderson.

Ayala's friend, Andrea Bailey, who is the vice-chair of that county's Board of Supervisors, remembered that race well.

"We prayed about it three consecutive times and we talked about it a lot until she says I'm tired of talking, I'm just going to do this thing," Bailey said.

Two years later, Ayala would win again. That win helped Democrats take full control of the statehouse for the first time in over two decades.

CORRECTION Virginia Election McAuliffe
Democratic candidate for Lt. Gov., Del. Hala Ayala, gestures during a rally in Richmond, Va., Friday, Oct. 15, 2021. Ayala will face Republican Winsome Sears in the November election.

"She worked her socks off," Bailey said.

Now, one of these two women will not only be Virginia's first female Lieutenant Governor, but also the first woman of color to hold that job.

The people who know each of them best said each deserved it.

"She is the perfect fit for the seat because of her fearlessness, her confidence because she knows what the state of Virginia needs," Bailey said about Ayala.

"She's a very strong woman, fearless and she's truthful," Drake said about Sears. "She'll tell you exactly what she thinks, and that's exactly what she is going to do."

Sears was born in Jamaica, but her family moved to the U.S. at a young age.

She served as a Marine before starting her own plumbing and electric business with her husband.

"Winsome has politics running through her veins because she was born and bred with politics, with her family into politics as far as in Jamaica," Donnalyn Ennels, one of Sears' best friends, said.

Ennels met Sears at church in Norfolk when their kids were young.

They bonded over their Jamaican heritage and their faith.

"That is the core of who Winsome the word of God, that's the core, I can put my money on that," Ennels said.

"I know the person who sat at the bedside with my sister whose two-year-old daughter was on a ventilator with leukemia. Winsome was there, that's just who Winsome is."

On the political front, Thelma Drake remembered Sears pushing to make sure schools were closed on Election Day to keep kids safe.

Winsome Sears
In this Sept. 1, 2021 photo, Virginia Republican Lt. Governor candidate Winsome Sears addressing the Virginia FREE Leadership Luncheon in McLean, Va. Sears will face Democrat Hala Ayala in the November election.

"She actually worked with our school board and they made the promise that they would have a teacher workday so the bill never had to advance," Drake said.

Delegate Ayala, a single mom who used to work as a gas station clerk to support her family, relied on public assistance to rise up and become financially secure.

She is now a veteran cybersecurity professional.

"She's a doer, she's a survivor in all realms," Bailey said.

Andrea Bailey said Ayala's multi-culture background and her struggles help her relate to all different kinds of people.

"Healthcare was one of the things she did not have when she was doing that, she was the recipient of welfare and food stamps, so she knows that feeling, and she knows how that can catapult you to the next level," Bailey said.

Ayala's political mentor, Charniele Herring, the majority leader in Virginia's House of Delegates, said she entrusted Ayala with a leadership position to help Democrats get votes.

"I did make her the Chief Deputy Whip in the caucus and brought her into leadership because she was about the team and helping and making sure we were pushing forward our policy agenda," Herring said.

And, even though they both have very different policy positions, regardless of who wins, history will be made.

A glass ceiling will be shattered.

"I always say there are people with auras, she is a bright aura," Herring said about Ayala.

"She goes the extra mile to make you feel welcomed, to make sure you're comfortable with her," Ennels said about Sears.

Speaking of policy positions, Ayala said she wanted to expand Medicaid, invest in school infrastructure, support small businesses and help Virginians, in particular women, get back to work.

Sears said she wants to promote school choice, especially in failing school districts, enact a small business tax holiday, invest in historically black colleges and universities, and raise police pay.