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None of the five candidates seeking the Republican nomination for U.S. Senate to run against Democrat Tim Kaine have ever held public office. In some quarters, that’s considered a plus.
Some of them, though, have tried. One of them has tried more than any other.
In 2010, Virginia Beach attorney Chuck Smith ran for the U.S. House of Representatives against Rep. Bobby Scott, D-Newport News, in the 3rd District but lost, as Republicans typically do in that strongly Democratic district. In 2012, Smith ran for the Kempsville district seat on the Virginia Beach City Council, but finished fourth out of a field of four candidates. In 2017, he unsuccessfully sought the Republican nomination for attorney general but failed to qualify for the ballot. In 2021, Smith did far, far better: He came within 3.4% of defeating Jason Miyares for the Republican nomination for attorney general.
There’s no shame in running and losing — lots of famous politicians lost before they won. Among them was a fellow named Abraham Lincoln, whom we think pretty highly of today.
Now for the part of Smith’s quest for public office that not many may know about: It started 37 years ago in Roanoke, when Smith mounted a brief quest for the Republican nomination for the state Senate — dropped out, bashed the Republican leadership, endorsed the Democratic candidate and announced he was switching parties.
When I called Smith to talk about it, he repeatedly asked me how I knew about this and accused me of being the recipient of opposition research from one of his four rivals for the Republican nomination. “I know,” he said. “One of my opponents has approached you and told you this guy has more experience than all the others, so here’s a question to ask him.”
The truth is far less interesting. I was there.
I was with The Roanoke Times from 1982 until 2021, when I left to help launch Cardinal News. In 1987, I literally had a front-row seat for Smith’s campaign, which began with the most unusual campaign announcement I’ve ever witnessed. First, though, the background.
Smith was born in Greensboro, North Carolina — on July 4, he proudly points out — and moved to Philadelphia at age 5. When he graduated high school, he joined the U.S. Marine Corps. After the Marines, he graduated from North Carolina Central University and went on to earn a law degree. At that point, he went back into the service, as a lawyer in the U.S. Navy’s Judge Advocate General program. Some of his Senate opponents play up their military service; Smith notes he’s the only one who has been in two branches of the military.
There have been no public polls in the Republican Senate contest, but, from a distance, Smith ought to be taken seriously. He did run that surprisingly tight race against Miyares. On the first ballot of that ranked-choice voting contest in 2021, Smith took 34.45% of the vote in a four-way race, just behind Miyares’ 36.56%. Miyares eventually won on the third round, but barely — 51.7% to 48.3%. In this year’s Senate primary, Smith ranks fourth out of the five Republican candidates for fundraising, but is not wildly out of line with the second and third place fundraisers. I’ve written many times before that money is not the sole determinant of political success. Finally, Smith does enjoy the endorsement of former state Sen. Amanda Chase, R-Chesterfield County, a well-known conservative firebrand who conceivably could sway some party activists in a multi-candidate race. Smith is also the only candidate in the Republican field who isn’t from Northern Virginia. If geography plays any role in the voting — and increasingly it seems to matter less and less — Smith does have a home field advantage in the state’s second-biggest metro area. And he may be the only one with any ties to the largest city in the western part of the state.
Smith says he first came to Roanoke to take the Virginia bar exam — the city is one of the traditional sites for that test. Later, he met a woman from Floyd County and got married at Roanoke’s High Street Baptist Church, then pastored by the city’s popular mayor, Noel Taylor. (Smith says he thinks Taylor officiated but he’s not sure.) Through much of the 1980s, Smith lived in Roanoke, operating a solo legal practice. Smith says he often received legal advice from another young attorney in town: David Bowers, who would go on to serve 16 years as mayor as a Democrat, and now is running this fall for mayor as a Republican. (Bowers confirms this but jokes that he can’t remember what advice he gave.) Smith says he often drove a motorcycle to work, which he always parked on the second level of a downtown parking garage — except for one fateful day in November 1985, when he parked it on the first level. That proved to be a mistake, because that was the day of the still-infamous Flood of 1985 that swamped downtown. “It was totaled,” he says. He says he also attended High Street Baptist Church, then and now one of the biggest congregations in the city.
In 1987, Smith let it be known that he’d like to seek the Republican nomination for the state Senate. The seat then was held by Granger Macfarlane, a Democrat who had defeated a Republican incumbent four years before. At the time, the district comprised the Democratic-voting city and much of Republican-leaning Roanoke County. However, neither locality was as partisan as they are now, and the district was considered quite politically volatile. A longtime Democratic incumbent (Bill Hopkins) had been upset in 1979; his Republican successor (Ray Garland) lost in 1983, so in 1987 there was no guarantee that Macfarlane would be reelected. Republicans were scouting about for a worthy challenger and first thought Carter “Chip” Magee, a prominent attorney, would run, but he passed on the race due to the press of business. Next, Republicans hoped to lure S.D. Roberts Moore, another prominent attorney in Roanoke who was known by the nickname “Rabbit.”
Then Smith entered the scene.
First, Smith applied to the Roanoke City Council for an appointment on the school board. Then, when Magee said he’d pass on the race, Smith told The Roanoke Times & World-News (as it was known then) that he was “seriously considering” a bid for the Senate nomination.
“I just remember him popping up from nowhere,” says Gilbert Butler Jr., who was the Roanoke Republican chair then. “No one knew anything about him or where he came from. He’d had no involvement with anyone in the party on the local level.”
I remember Republicans being mystified by this newcomer. On the one hand, a young Black attorney would make a demographically interesting candidate in Roanoke, a city with a Black Republican mayor in Noel Taylor, who was at the time easily the most popular politician in town. On the other hand, Republicans had their hearts set on a big-name candidate, and that certainly wasn’t Smith.
“If the competition for the Republican nomination is keen, I might consider stepping aside for party unity,” Smith told the newspaper in that classic “testing the waters” story. “But I believe you have to seize the moment and now we have an opportunity [to beat Macfarlane]. And I think I might have some assets that other candidates might not enjoy.”
That was March 17, 1987. Two days later Smith announced he was withdrawing his school board application to focus on a possible Senate campaign. He also said that Taylor had encouraged him to run — and the mayor confirmed this. “He is a brilliant young lawyer with a sincere interest in the area,” Taylor told the newspaper. Party leaders, though, remained mystified by the unknown Smith.
On April 2, Smith scheduled a news conference at his law office on Luck Avenue. The Roanoke newspaper still published an afternoon edition then, with a final copy deadline of around noon at the absolute latest. A late-morning news conference posed deadline challenges. This was also long before there were cellphones. That’s why the paper sent two reporters to Smith’s event — one of them being me. Political reporter Rob Eure was there to write the story. My role was to stay just long enough to confirm that Smith was, indeed, running — and then run back to the newspaper office (about three blocks away), so that editors could hold space for Rob’s story.
Smith did, indeed, announce. He also began by saying that party leaders didn’t want him to run — and proceeded to reveal some personal details about himself that would not be flattering in a campaign, particularly in that era. Specifically, he said that he’d been sued for credit card debts in North Carolina and had fathered a child out of wedlock — a 5-year-old daughter in Norfolk “whom I love more than life itself but have never been formally married to her mother.” He said that he was “raising these issues up front that might be negatives so I can go on with a positive campaign.”
I remember racing into the newsroom and describing this to Dick Hammerstrom, an assistant city editor who was responsible for the afternoon edition. He thought I was joking. I assured him I was not. Rob’s story, which appeared that afternoon, was headlined: “Republican State-Senate candidate tells all in announcement.”
Smith also said he would drop out of the race if Moore entered. Moore did not. Republican leaders, wary of Smith, kept looking for a big-name candidate and eventually found one in William “Ham” Flannagan, the retired president of Roanoke Memorial Hospital. Smith said he might run as an independent, according to The Roanoke Times & World-News. The paper also revealed that Smith was such a newcomer to politics that he hadn’t registered to vote until a few days before he announced his candidacy.
On June 1, Smith dropped out entirely. In my recent interview with Smith, he said that a Roanoke Republican, whose name he said he couldn’t remember, had encouraged him to run — but then never followed through with support and eventually backed Flannagan. That matches with what Smith said at the time: “In my efforts to seek the Republican nomination for state Senate, I have tried to play fair. The Republicans sought me out. I announced. Then they spent all their time trying to find someone else to nominate.”
Butler, the city Republican chairman, told the paper then that Smith’s accusations were “a complete fabrication.” The paper quoted Butler: “I had never heard of Chester Smith until he called me one day and said he wanted the Republican nomination.” None of that is contradictory: Parties aren’t monoliths. It’s entirely possible that someone encouraged him to run — and that the unit chair was completely unaware. Smith also told me in our recent interview that while he was running for the state Senate, a Republican from Richmond — whose name he said he’d also forgotten — called and offered him $10,000 to quit the Senate race and run for the House of Delegates instead. “I remember saying I was a man of integrity” and wouldn’t do it, he told me. This is also quite plausible. At the time, the Roanoke Valley had four House seats, three of them held by Democrats. Republican challengers were hard to find. A $10,000 contribution to jump-start a challenge to one of them — especially if it avoided a contested nomination for a Senate seat the party thought was within reach — seems realistic.
In any case, Smith stayed in the Senate race — until he didn’t. Then, however, comes the most unusual part of the story. Smith didn’t just drop out. He bashed Republicans and said he was switching parties. In his withdrawal statement, Smith said he had “made the wrong choice” to run as a Republican. “The Democratic Party is my home and I do believe people should work through the system,” he said then, according to a story in The Roanoke Times & World-News. “I intend to support the Democratic Party and work with Granger Macfarlane to continue as our senator. The issues are clearly drawn. I have decided to withdraw and return to the party where I feel at home.”
The story was headlined: “Chester Smith drops Senate bid, endorses incumbent Macfarlane.”
Smith told me that not long afterwards, he and his wife divorced and he moved out of town, settling in Virginia Beach where he’s practiced law and taken part in Republican politics since, at one time serving as Republican unit chair in the city.
All the coverage in the Roanoke newspaper in the ’80s referred to Smith as “Chester,” although he says he’s always been known as “Chuck.” But newspapers often prefer formal names. Because of that Chester/Chuck variation, I didn’t realize in 2021 that the Chuck Smith who was running for attorney general (and nearly defeated Miyares for the nomination) was the same Chester Smith who years before had run in Roanoke, then left the party. No one else seems to have realized this, either. Butler, who was Republican chair then, said he wasn’t aware of the connection until I pointed it out to him. All he remembers about Smith is that “there was no enthusiasm for his candidacy — for the reason nobody knew him or knew anything about him.” Ross Hart, who was Roanoke Democratic chair then, said he doesn’t remember Smith at all, even though he was quoted in some of the stories at the time calling Smith “a man with a lot of energy and some good ideas.” (This was after Smith said he was changing parties.) “It was just merely 40 years ago,” Butler told me.
When I talked recently with Smith about his Roanoke days and his state Senate campaign, he said he didn’t remember endorsing Macfarlane, but also said he was upset at the time because he felt the Republican activist who had initially encouraged his candidacy had failed to follow through with support. “I was mad the lady switched sides — I was very, very, very upset at that lady,” he told me. Smith said he’d always considered himself a Republican from the time he started paying attention to politics. As for his 1987 announcement that he felt more at home with Democrats, “the only thing I can attribute it to is my anger,” he said. “I may have endorsed him [Macfarlane], but I didn’t vote for him.”
As parties realign, politicians often switch parties. The Republican who was president in the 1980s, Ronald Reagan, once was a Democrat. What’s more curious is what Smith says now about the circumstances of his Roanoke candidacy. I shared with him copies of stories that appeared in the newspaper. “The statements attributed to me are totally false,” he told me. “I don’t remember any of them.” What about all his quotes at the time? “I don’t know what to tell you,” he said.
In this week’s West of the Capital newsletter:
I write a free weekly political newsletter that goes out each Friday at 3 p.m. You can sign up for that or any of our other free newsletters on our sign-up page. If you’re really into politics, I recommend our Cardinal 250 newsletter, a monthly newsletter on the little-known stories of Virginia’s role leading up to the Declaration of Independence. Part of our monthly package includes a column by me where I write about the politics of that era the same way we’d write about them today. As for more contemporary politics, here’s what’s in this week’s West of the Capital:
- A consumer advisory on how to read the latest polling, including an internal poll that purports to show John McGuire leading Rep. Bob Good in the 5th District Republican contest.
- A look how the next seven days will be big ones in terms of the state budget and legislation that Gov. Glenn Youngkin has yet to act on.
- More candidates for the Democratic nomination for attorney general.
- A nonpartisan group ranks every member of Congress in terms of their bipartisanship. One Virginia House member scored exceptionally high, another near the bottom — and they’re from the same party.
- How one candidate solved a problem when there wasn’t enough space to put up his signs at the registrar’s office.