Walking through Henrico County’s Jail West, Alisa Gregory stops to talk, and listen, to dozens of deputies and inmates alike.
“I can walk through the jail and not come out for hours,” Gregory said in an interview in her office earlier this month.
Even before she officially takes over as sheriff, they know she’s the one to get their questions answered, their issues handled or their voices heard.
“She’s always been a good go-to person for getting stuff done,” said outgoing Sheriff Mike Wade.
It’s been a few weeks since Gregory, 50, won the election to succeed Wade, making her the county’s first female and African American sheriff. Wade officially retires Dec. 31 but is taking the entire month of December off, so Gregory took the reins Wednesday. She won’t officially be sworn in until Dec. 11.
She said it’s her compassion and love of people that drove her to run for a role she never envisioned for herself. The constitutional position is charged with security at Henrico’s courts and at Jail West in Henrico and Jail East in New Kent County. The sheriff’s office also executes mental health commitment orders and serves civil process documents. The department Gregory is inheriting is one of the largest in the state with 403 total staff members, including 321 sworn deputies, and it has an annual budget of $42.5 million.
“It used to be that the most I could be here is chief deputy; then the sheriff created undersheriff,” Gregory said of the position she held until becoming the top brass. “But because the position is elected, it’s going to be a man or it’s going to be a police officer, because that’s what it had been in the past. But to now see that I can come here and the sky is the limit.”
The fact that she was a woman never really crossed Wade’s mind when he was looking for his successor, he said.
“I just thought she was a deputy, I didn’t realize she was a female,” he said. “To think that a female couldn’t come to the top would be ridiculous today. I think it’s about caring for the inmates and the employees, and she’s certainly shown that.”
But she’s no pushover either, Wade said, remembering when she was upset with him when he assigned her to an overnight security post. But she said she’s glad now because it means she’s worked in nearly every department in the office.
Wade first encouraged Gregory to run for the Republican nomination. Wade won as the GOP candidate in each of the five elections starting when he was first elected in 1999, and formerly chaired the county’s Republican Party. But when Gregory instead turned to the Democratic Party, which she said better matched her own ideals, Wade resigned from his party to support her.
“That’s how strongly I believed that we needed someone like her,” Wade said.
The Highland Springs High School graduate still lives in the Varina District of Henrico with her husband. She raised three children there and tried to instill in them the same principles of compassion that her grandmother did in her.
“My grandmother had the house where everybody could come,” she said. “Whether it was family or friends that came, they knew that if they were on hard times or if they had done something, that you could come to my grandmother and not only was she going to love you, give you her best, take care of you, she was not going to judge you.
“Because everybody makes mistakes,” she continued. “We all make mistakes.”
Gregory said she didn’t realize it until now, but her grandmother’s house served as her first example of what a recovery house could be and what it could do for people.
One of the most pressing issues at the two county-run jails is overcrowding. Inmates with substance-use and mental health issues are largely contributing to this, she said, and so she’s looking for ways to “triage” them. That means quickly identifying those people who could benefit from programs or alternative sentences that might mitigate the issues that brought them into the jail.
“We want to work on the person; reduce recidivism; we want to stop the cycle for some of them, the revolving door for some of the folks,” she said. “People need to know that someone has faith in them. They have to know that there is still hope. And that’s what we should be doing. That’s what people should be getting when they come into jail. You’ve hit that place, now how do you turn it around and get back on track?”
Gregory said the nationally recognized drug rehabilitation programs Wade started, RISE and ORBIT, “are here to stay.”
“I think the sheriff was a pioneer before his time,” she said of Wade, whom she has worked under throughout her 21-year tenure except for one year. “I think he has set a new precedent for what our correctional institutions should look like: true rehabilitation. Being able to address the issues that sometimes bring people into correctional institutions or jails. I think we can only enhance and get better with those programs.”
She also wants to thank those who supported her rise, and her way of doing things. She acknowledges that the system is already built around punishment, but said it could also go a long way in helping people leave jail better than they came in.
“If that’s soft, then a lot of people in the community want a soft sheriff,” she said of her platform of compassion. “I think it’s a caring sheriff.”
While campaigning she met a young woman who had been incarcerated when Gregory had just started working at the sheriff’s department. The woman now is a business owner.
“To have her tell you that you were a part of that, because you believed in them, that’s huge,” she said. “To know that you are a positive impact on somebody’s life and they can turn it around and they can be a productive part of the community. That’s why I do it.”
Wade said he believes Gregory is “set up to succeed.”
“If she does great, it’s what I taught her; if she doesn’t do well, she didn’t listen to me,” he joked.