by Andrew Kerley, Politics & Policy Reporter
With Jackie McDonnough, a Democratic-Socialist educator, having won Richmond City’s 6th District School Board election by nearly two-thirds of the vote — the Richmond Democratic Socialists of America are planning to expand their influence and run more candidates moving forward.
McDonnough defeated the incumbent appointee Anne Holton, who raised the most money for a Richmond school board race in modern history, in the special election to fill the vacancy left by former board member Shonda Harris-Muhammed’s departure.
Holton raised $110,436 in donations, dwarfing McDonnough’s $32,547. Holton had the endorsements of two mayors, three governors — including her husband Sen. Tim Kaine — and most of Richmond’s General Assembly delegation. Still, with a small army of young, progressive volunteers to knock doors and make calls, McDonnough took the seat.
Riding off their big win, the Richmond DSA — which also helped elect Richmond Del. Charlie Schmidt and 3rd District City Councilor Kenya Gibson in past years — is setting its sights on future local and state races it could win.
A shocking win
McDonnough — who taught for decades in Richmond and Chesterfield public schools, and also at VCU as an education professor — was not expecting to win by such a large margin.
“When we talked to people about Jackie, it was a lot of realizing that the way that politics has been happening from both the Democrat and Republican side never speaks directly to people,” said Elisabeth Waldron, co-chair of Richmond DSA. “I think Jackie’s campaign showed us that people have the power, and they can take it back and it belongs to them.”
As the campaign worked to knock on over 11,000 doors across the “Gateway District” spanning through downtown Richmond, Northside and Southside, McDonnough knocked on 1,000 of those doors herself. She took notes on what Richmonders complained about their school system — from bad school lunches to the quality of special education programs.
“It was almost as if they had never been asked,” McDonnough said.
Virginia political analyst Dr. Richard Meagher, a professor at Randolph-Macon University and host of the “RVA’s Got Issue” podcast, was not just surprised by McDonough’s win, but by the fact of how big the margin was.
“It was quite a surprising result for folks who thought this is someone who is Virginia politics royalty — the daughter of a governor, a former secretary of education, wife of Tim Kaine,” Meagher said. “This is somebody who’s really well connected and also well respected among certain circles. It’s not like she’s some obvious demon that needed to be taken down, or someone with a corrupt past.”
Holton officially conceded on Wednesday morning. She congratulated McDonnough — saying she cares deeply for Richmond students and families.
“While the outcome was not what we had hoped for, this campaign has been the experience of a lifetime,” Holton stated.
Meagher said there is a sense that the old guard of Democratic power brokers in the city is losing steam. In some cases, they are getting older without a new generation to replace them. As that happens, new political forces are arriving, such as Richmond for All.
RFA was the other big group that backed McDonnough and her grassroots campaign. Additional McDonnough allies included the Richmond Crusade for Voters and the Richmond Caucus of Rank-and-File Educators.
RFA ideologically aligns with Richmond DSA most of the time, but not all the time. Both groups endorsed Gibson and Schmidt in their races. But RFA also endorsed Harris-Muhammad, who went on to endorse Holton over McDonnough.
“We should be careful of simplifying this as ‘the DSA candidate won,’” Meagher said. “Jackie is much more than that. She is a DSA candidate, but she came to the DSA with a very deep set of roots in her district, in her school system … a former teacher, well respected.”
Richmond DSA wants more candidates ‘like Jackie’
Richmond DSA co-chair Elisabeth Waldron told Virginia Scope that their organization is considering running more candidates, either on the local level in 2028, or for the General Assembly in 2027. The former is more likely at the moment, but “the sky is the limit,” she said.
“Were trying to find candidates who are just like Jackie — knocking doors, talking to people, talking to their neighbors, talking to people who know genuine people who have put in the hard work all of their lives and never been given the recognition they deserve,” Waldron said in a video interview Tuesday night.
“I think that’s what DSA is striving for,” she continued. “Align everyday working people, who may not know how all the processes work but are willing to put in the work to learn those processes, into office, because we’re tired of the establishment. They are not offering anything for us, from the Democrats to the Republicans. We need change.”
Richmond is one of the most Democratically-oriented cities in the country, according to Virginia political analyst Dr. Bob Holsworth. It would make sense for DSA candidates to do well there, as the New York City DSA has done with Mayor Zohran Mamdani.
McDonnough previously told Virginia Scope that Mamdani and the NYC DSA were direct inspirations for their campaign, and their hope to ultimately build a new political machine in Richmond.
“What I wonder is, are you going to see an even larger effort by Democratic Socialists in the next city council election and potentially the mayoral election?” Holsworth said.
Holsworth named Richmond’s 2nd, 3rd and 6th Districts as potentially strong areas for the Richmond DSA to run new candidates for City Council or School Board.
“Who knows about the 2nd because of the [Virginia Commonwealth University] students. If you organize with VCU students, [they’re] very difficult to beat,” Holsworth said. “And if all of a sudden they have a very strong Democratic Socialist candidate [for president], they will be competitive.
U.S. Rep. Alexandria Ocasio-Cortez, D-New York, could end up being that figure to energize young voters, as she regularly polls among the top contenders for the Democratic nomination for president in 2028. The 37-year-old recently visited Northern Virginia to campaign with Rep. Eugene Vindman, D-7th District.
“As DSA, we actually have started having those discussions about endorsing for the presidency,” Waldron told Virginia Scope in a later interview. “The window is definitely open for that to happen, given this extreme blue wave this past midterm,” she continued.