NEWPORT NEWS — She’s undertaking something rare in Virginia — running against a city’s longtime top prosecutor.

Shannon M. Jones, 40, is attempting to unseat Newport News Commonwealth’s Attorney Howard E. Gwynn , the second longest-serving elected prosecutor in Virginia. He’s worked in the office for 43 years and led it for 35.

Gwynn and Jones will face off in the Democratic primary on June 17, the first time since his first election in 1990 that Gwynn has an opponent.

Jones, an assistant city attorney in Newport News, worked for Gwynn twice — once for just over three years and another for about eight months — and has considered him her mentor. But now, she maintains, it’s time for a new direction.

“We’ve just gotten such a positive response from the community,” Jones said. “People are very ready for change.”

The commonwealth’s attorney’s office under Gwynn is strong in its “ability to prosecute cases,” Jones acknowledged. That strength, she said, is a good “foundation” to build on.

The office of 70 people — including about 30 prosecutors — handles some 4,800 felony and misdemeanor cases annually.

Community outreach

“But I think that right now, in public safety, the focus is on doing more than just that,” Jones said.

Just as the Newport News Police and Fire Departments do a lot of community outreach, she said, prosecutors should “build trust in the justice system” by doing such things as attending local football games and neighborhood watch meetings.

“I think that’s really what our community wants to see us doing — focusing on our youth, not just prosecuting cases, but focusing on prevention,” she said.

Jones has the support of Newport News Mayor Phillip Jones, who calls her “the visionary leader Newport News needs for the future.”

Gwynn said his attorneys do attend some neighborhood watch events. He also has an employee for community outreach and recently launched an advisory board of community stakeholders.

But he noted that the city, the school division and other groups spend “millions of dollars” on community outreach already. The primary role of his office, Gwynn said, is keeping the city safe through effective prosecutions.

“The attorneys are incredibly busy prosecuting jury trials,” he said. “Our job is to keep the venue safe so children can go to these programs without fear.”

Jones countered that having prosecutors more visible in the community would “make it more likely” that witnesses would cooperate. “It assists us in our ability to prosecute cases, which thereby makes us safer,” she said.

Small town girl

Jones grew up in Pink Hill, North Carolina, a 500-person town about an hour south of Greenville. “I’m a country girl, like running through corn fields and being outside is how I grew up,” she said.

When her parents split when Jones was in high school, she and her mother moved to Virginia Beach. “For me, Virginia Beach was the big city,” she said. She was excited to be in a diverse place with “people from all over the world.”

Jones attended Tallwood High School, then Old Dominion University, where she majored in psychology. She was active in the university’s NAACP program, and “I fell in love with civil rights.”

She served on statewide college leadership roles in the NAACP. After graduating from ODU, she moved to Washington and began working for a small non-profit focused on educational opportunities for youth.

Becoming a lawyer

It was while working in D.C. that she attended a protest outside the U.S. Supreme Court during a voting rights case. It was then that she decided to become an attorney.

After the hearing, the lawyers came outside and told the crowd about the case they had made in the courtroom. Students from nearby Howard University Law School also spoke about the legal briefs they had filed that referenced their school’s civil rights legacy.

“I want to be inside the courthouse,” Jones said she told herself. “I’m going to law school, and I’m going to Howard.”

After graduating from Howard Law in 2013, Jones landed a job at the Philadelphia District Attorney’s Office.

She initially thought being a defense attorney rather than a prosecutor was more in line with civil rights. But her experience in Philadelphia “taught me that the most powerful people in the criminal justice system are prosecutors, and that we need people who are social justice-minded to be on both sides.”

After about 2 1/2years in Philly, she worked as a civil rights investigator in Prince William County while studying to take the bar exam.

Gwynn hired her in December 2016.

‘Looked up to Howard’

“I looked up to Howard a lot,” Jones said. “I felt like we had a mentor-mentee relationship. I felt really comfortable to go and talk to him a lot about cases and my viewpoints on things.”

One practice in Philadelphia that she wants to bring here, she said, is to “divert” more cases rather than taking them to trial — with defendants instead paying restitution, doing community service or going to anger management and substance abuse classes.

“There are some people who absolutely need to be prosecuted, and they absolutely should be removed from our community,” Jones said.

But for lower-level offenses, she said, “what you hear me talking about a lot is … rehabilitation and getting folks back on track.” She wants more discussions between prosecutors, public defenders and defendants at the front end, as was routine in Philly.

“They tell me what their side is, and I tell them what my side is,” Jones said of that process. “I have found we are able to work things out a lot easier. We’re able to streamline things and really focus on justice.”

After about three years working under Gwynn, Jones left in January 2020 to work at the Hampton City Attorney’s Office, handling civil matters on such things as compliance with city codes, the Americans with Disabilities Act and risk management.

“I left on really good terms with Howard,” she said. “We stayed in touch. I continued to talk to him quite a bit.”

Returning to Newport News

But in the summer of 2020 — as the pandemic was in full bloom and the George Floyd protests were underway — Jones contemplated her role in life.

“I was really thinking about my law school experience — the civil rights piece of my background, and I felt like I wanted to do more,” she said. “I called Howard, and I told him that I was interested in running when he retired.”

Gwynn reacted positively, she said, though he told her she would need to come back to work for him if she wanted his backing. Jones believed Gwynn was planning to retire by 2023, and “I saw it as my opportunity to kind of step back up.”

“I would not say that he made any promises,” she said. “But I believed that he was close to retirement.”

Jones returned to Newport News in June 2021, believing Gwynn would support her running for the job a couple years later. Upon her return, she handled several jury trials and formed a mock trial program for high school students at the Achievable Dream Academy.

But it soon became clear, Jones said, that Gwynn wasn’t retiring in 2023 — or even in 2025. It became apparent “very quickly,” she said, that “he planned on staying for much longer.”

‘Keep your head down’

Gwynn says he did not tell Jones or others in 2021 that he was planning to retire, even as he had a health issue around that time. “People may have speculated about it, but nobody talked to me,” he said.

Moreover, Gwynn said he re-hired Jones in 2021 against the recommendation of some of his top deputies.

During a panel interview with Jones, one of Gwynn’s longtime deputies, Ruth Burdge, “was very direct in questioning Shannon … about the quality of her work,” he said. “It was the unanimous opinion of the interview committee that she not be hired back.”

Gwynn said Jones called him on the way home, upset that Burdge had “grilled” her during an interview that had gone “badly.”

“But because I believed in her, I went against the wishes of the people that I trusted,” Gwynn said of Jones. “I said, ‘I’m gonna hire you back in spite of what the committee wants.’ I told her to ‘keep your head down, do your job and prove them wrong.'”

Jones declined Friday to respond to Gwynn’s recounting of her 2021 re-hiring. “The time I spent in the commonwealth’s attorney’s office was incredibly beneficial to my professional development.”

City Attorney’s Office

Jones stayed with the office for about eight months before telling Gwynn in February 2022 that she was taking a job with the Newport News City Attorney’s Office. A spot working with public safety agencies had just opened up.

“God just opened the door,” Jones said.

The job at City Hall — across the street from the Commonwealth’s Attorney’s Office — “has been the best thing ever,” Jones said. She advises the Newport News Police and Fire Departments on legal matters ranging from immigration law to open records to Fourth Amendment issues pertaining to drone technology.

“The range of legal issues that our public safety departments deal with is so wide,” she said. “I get these random phone calls from our chief of police or our fire chief or whomever, and it’s the most random questions, and I have to make quick assessments.”

Mayor Jones, for his part, cited Shannon Jones’ role with the City Attorney’s Office in his endorsement, saying she “has the knowledge and readiness to serve from day one.”

“I think I know everybody at City Hall now,” Jones said. “And I feel like, when I get elected — I want to speak that into existence — I have all these relationships with all these people. They know me. I’m not an outsider.”

Prosecuting misdemeanors

In one of many policy prescriptions, Jones wants to increase the number of misdemeanor cases the commonwealth’s office handles.

While Virginia commonwealth’s attorneys by law only have to prosecute felonies, Gwynn’s office also prosecutes misdemeanor domestic assaults, DUIs, elder abuse and crimes involving guns, drugs or schools, among others.

But Jones wants to add other assaults, larcenies, stalking, trespassing and many other misdemeanors to the list.

“If you’re a victim of an assault and battery that’s not a domestic violence case … you should have a prosecutor there with you,” she said.

She said two prosecutors could handle the increased workload at a twice per week docket — and that they would constantly be evaluating cases for diverted outcomes rather than trials.

Gwynn said his prosecutors are working hard to keep up with felony cases, with a jury trial backlog stemming from the pandemic and a change in sentencing law a few years ago that caused more defendants to opt for jury trials.

“In an ideal world, we should prosecute every misdemeanor case, because the system would be better if we did,” Gwynn said. “But we don’t live in an ideal world. Unfortunately, there is no way that this office can prosecute every misdemeanor.”

Handling the thousands of extra cases Jones wants to, Gwynn said, would take many more than two prosecutors. Though Virginia lawmakers considered requiring prosecutors to handle more misdemeanors, they balked at the hundreds of millions of dollars it would take to pay for it.

Jones, for her part, contends taking on more misdemeanor cases will keep defendants from “slipping through the cracks,” and she asserted that focusing on misdemeanors would reduce felonies in the long run.

“We want to get to them sooner, focus on prevention and stop them from ever getting to that felony level,” she said. “That’s going to help reduce all those more serious offenses that we’re seeing.”