Midterm madness: Can the 5th district be flipped?

Leslie Cockburn and Denver Riggleman faced off at PVCC in October. Photo: Sanjay Suchak Leslie Cockburn and Denver Riggleman faced off at PVCC in October. Photo: Sanjay Suchak

In any other year, the Republican incumbent in the 5th District would be a shoo-in. But this year, two things make the election something of a horse race: One, Congressman Tom Garrett announced in late May that he would not seek a second term, leaving an open seat without the incumbent advantage. And two, Donald Trump was elected president in 2016. Can the 5th be flipped?

Traditionally, the midterms are the elections for which voters don’t bother showing up. (Our story on the last one was subtitled “What if you held an election and the voters didn’t care?”) But that political landscape has decidedly changed.

This year, citizens are practically frothing at the mouth to get to the polls. Democrats are predicting a blue wave powered by outrage at Trump and the recent confirmation of Brett Kavanaugh to the Supreme Court. Republicans are declaring that backlash to the Kavanaugh hearings and the fear that Democrats will impeach Trump will surge into a red swell.

And the polls…well, after 2016, no one’s going to call a close race based on polls.

Charlottesville is a blue dot in the solidly red swath of the 5th District, which runs from Southside on the North Carolina border to horse-farmy Fauquier County in northern Virginia. The district hasn’t elected a Dem since Tom Perriello won along with Barack Obama in 2008. Perriello served one term, and the district reverted to its rural red roots.

But in the wake of the highly controversial 2016 presidential election, a whole lot could change.

“Trump’s victory in 2016 basically imperiled a lot of Republicans in 2018,” says Kyle Kondik of Larry Sabato’s Crystal Ball, the UVA-based newsletter that rates races across the country.

The real estate developer/reality TV star’s win inspired veteran journalist and Rappahannock resident Leslie Cockburn to enter the race. She emerged victorious from somewhat bitterly fought Democratic caucuses throughout the 5th.

And Garrett’s abrupt retirement from Congress left Republicans scrambling to find a candidate. Emerging with the nomination was Denver Riggleman, a defense intelligence contractor and distiller, who made a brief stab last year at securing the GOP’s gubernatorial nomination, which fell to longtime operative Ed Gillespie.

With two political newcomers, pundits moved the race from “likely Republican” to “leans Republican.”

Among the many opposition groups spawned by Trump’s election is Indivisible, a national organization whose Charlottesville members were enraged by Garrett’s solid support of the president’s attempts to repeal the Affordable Care Act and his unwillingness to meet with Charlottesville constituents.

“We’re working hard to flip the 5th District blue because it’s important to have a congressman who cares about the people of this district,” says Indivisible’s Dave Singerman.

He’s undeterred by the Republican-heavy district. “One of the things I learned after the 2016 election is that predictions don’t matter and polls don’t matter,” says Singerman. “Getting out there and knocking on doors is what matters.”

Cockburn has an army of more than 1,500 volunteers going door to door, and the “energy is extraordinary,” he says.

“I’m not seeing that energy with Denver,” says Singerman. ”I see big signs the campaign puts up. I see a lot of little Leslie ones in people’s yards.”

Leslie Cockburn is part of a blue wave of women running for office following the election of Donald Trump as president. Publicity photo

Kondik rates the race “leans Republican,” and while he won’t put odds on the chances of flipping the 5th, he says, “I’d certainly rather be a Republican than a Democrat in that district.” The district, which was redrawn after the 2010 census, has been altered to be a little more Republican than when Perriello won it in ‘08, he says.

Kondik has heard of polling on the Republican side that shows “Riggleman up by a little.”

Some forecasters, such as Nate Silver’s FiveThirtyEight, like the Democrats’ chance in the 5th and are calling it a toss-up.

“Democrats have run some serious campaigns in this district,” says Kondik, but he notes that former Albemarle supervisor Jane Dittmar lost in 2016 by 16 points, in a state that Hillary Clinton won by 5 points.

In statewide elections, Virginia has elected Democrats since 2012. But that doesn’t hold true for the 5th, which Trump carried by 11 points in 2016. Last year, Dem Ralph Northam won the governor’s race by 9 points statewide—but lost in the 5th by 9 points to Republican Gillespie.

The U.S. Senate race pitting popular former governor and incumbent Democratic Senator Tim Kaine against Confederate flag-loving Republican Corey Stewart could be a factor in the congressional races, Kondik says.

“Stewart could lose in a landslide statewide and drag down others,”  says Kondik, who predicts that Kaine will win the state by 15 points, likely carrying the 5th.

He puts the 5th No. 4 in a list of flippable Republican-held congressional districts, with Barbara Comstock No. 1 in the 10th, followed by Dave Brat in the 7th and Scott Taylor in the 2nd. In Northern Virginia, where Trump is wildly unpopular, “Comstock is in trouble.” But the other competitive districts in the state “are not as Republican as the 5th.”

Both parties have congressional committees that fund House of Representative races, and the 5th “is not a district that comes up in those conversations,” says Kondik. “Parties become aware of close races and decide to come in at the last minute.”

Cockburn announced October 17 that the Democratic Congressional Campaign Committee had added her race to its Red to Blue list.

Female rage fueled by the #MeToo movement and the Kavanaugh Supreme Court nomination could be a factor in the race, particularly among college-educated, affluent women living in the suburbs, such as Comstock’s 10th District, says Kondick. The 5th “is not like that. It’s not an affluent, educated district as a whole.”

Melvin Adams, 5th District Republican Committee chair, thinks the Kavanaugh nomination will “absolutely” be a factor in getting out the vote—the GOP vote. “It’s not just about men,” he says. “Republican women are upset about this. They think it was a sham.”

Adams says Dr. Christine Blasey Ford, who accused Kavanaugh of assault when they were in high school, was a victim abused in the process. “She wanted privacy. She was dragged out like a little rag doll and used.”

And although Trump is not on the ballot, “He’s on the ticket,” says Adams. “That’s going to motivate a lot of people on both sides.”

As to whether the 5th will flip on Election Day in November, Adams says, “I can’t answer that until the 7th. I do believe the district by and large is more conservative than Leslie Cockburn.”

And according to Adams, “A lot of polls have taken this race out of the watch list.”

Denver Riggleman sought elected office after dealing with Virginia laws that hamstrung his distillery and threatened him with eminent domain for the Atlantic Coast Pipeline. Publicity photo

Others didn’t poll it at all. Quentin Kidd, director of Christopher Newport University’s Wason Center for Public Policy, says, “We didn’t do it because we didn’t think it would be competitive.”

Kidd notes that there hasn’t been a lot of outside money going into the race, like there has been in the 10th District. He has a hard time seeing a Dem upset. The district is drawn as very conservative, he says. “There are not enough Democrats in the 5th to overcome the numbers.”

“But in the back of my head,” he adds, “that’s what everyone was saying about Tom Perriello.”

The last Democrat to win the 5th is more optimistic. “I think [Cockburn] has a great chance to win,” says Perriello, citing her strong grassroots organization and her emphasis on issues that are important to Virginians, such as health care. “Open seats are a lot easier to pick up than those with incumbents.” 

Comparing this race to his win in 2008, Perriello says, “Ten years is a century in politics.” Then, there was a lot of energy coming from the candidacy of Barack Obama and his message of hope, he says.

“There is a very different energy from ‘08,” he says. “People are appalled by the corruption they’re seeing from the top down.” There’s a motivation to check “this era of fear.”

Perriello offers a different perspective on how Republicans in the district will cast their votes this round. “I don’t think Trump would carry this district today,” he says. “I think they liked him as an  outsider.” Now, he says, “I can’t tell you how often I meet people who voted for Trump who are deeply disappointed, while he’s cutting deals to benefit his family.”

He adds, “A lot of independent voters who were intrigued by Trump feel betrayed by Trump.”

Perriello challenges the notion that Cockburn is too far left for the 5th, and says the “spectrum of right, left, and center have become impossible to decipher.” Wanting affordable health care isn’t any less popular on the right than it is on the left, maintains Perriello.

Trump, he says, is “more extreme than anyone we’ve seen in the Republican party,” and has decimated traditional Republican values, such as fiscal responsibility, with his tax cuts that have ballooned the federal deficit while benefiting the rich, not his working-class base. “He’s only consistent on issues of racial divisiveness.”

Perriello, who notes he was never ahead in the polls, offers this for the 5th: “There’s only one poll that matters, and that’s the one on Election Day.”


The Issues

They’re on opposite sides of the political spectrum, but there are a few issues upon which Democrat Leslie Cockburn and Republican Denver Riggleman agree.




Healthcare is a basic human right



Support Atlantic Coast Pipeline



Decriminalization of pot



Climate change based on human activity



Food stamps



Russian election interference



Press is the enemy of people



Tax cuts



Build the wall



Restoration of felon voting rights


Not for violent crimes

Net neutrality



Muslim countries breeding grounds for terrorists



Raise minimum wage from $7.25/hour



Donations from PACs


Koch brothers

Restrict hate speech



*Doesn’t trust the recent UN report and doesn’t want to “take people’s jobs away. …I don’t want science to become a religion.”


The Candidates

Denver Riggleman

Age: 48

Resides: Afton

Occupation: Defense contractor/distiller

Grew up: Manassas

Education: B.A., University of Virginia; master’s certificate in program management, Villanova

Nickname: The Silverback

Author of: Bigfoot Exterminators Inc. The Partially Cautionary, Mostly True Tale of Monster Hunt 2006 (34 pages, self-published), The Mating Habits of Bigfoot and Why Women Want Him (we think this is a joke)

Denver Riggleman made his first, short-lived run for office last year, after butting up against the liquor industry and ABC regulations that impacted his Silverback Distillery, and Dominion’s plan to take his land in Nelson County for the controversial Atlantic Coast Pipeline.

“A lobbyist told me, ‘If you’re not at the dinner table, you’re on the menu.’” he said at an October 8 debate at Piedmont Virginia Community College.

Although his 2017 “Whiskey Rebellion” didn’t raise enough money to secure the Republican nomination for governor, Riggleman became the GOP’s 5th District standard bearer less than a week after Congressman Tom Garrett’s Memorial Day announcement that he would not seek reelection.

Riggleman comes from a modest background and said at the debate that he’d been on food stamps a couple of times. He told the Washington Post he was “a bit of a loser,” until his wife Christine became pregnant, which motivated him to join the U.S. Air Force and get a degree from UVA.

After leaving the military in 2003, Riggleman co-founded a defense contracting company, Analyst Warehouse LLC, which InDyne acquired in 2012. In 2014, he and Christine opened Silverback Distillery in Nelson County, and last year, they opened a facility in Pennsylvania because of that state’s friendlier liquor laws.

Riggleman stresses that he’s not a politician, and he endorses libertarian themes of minimal government intrusion into property rights and business. He also touts his military intelligence background.

Riggleman supports Trump, but he says he doesn’t agree with the president on everything, in particular the raised debt ceiling. “If you’re going to do economic stimulus through tax cuts, you have to make sure spending is down also,” he says.

He’s pledged to join the Freedom Caucus, the most conservative gang in the House, because he likes its fiscal policies, but he also says he differs with the group on the social issue side, and as “an independent-thinking guy” he won’t be in lockstep with it.

The biggest difference between Cockburn and him? “I believe individuals should control their lives,” he says. “My opponent believes the government should have a bigger role than I would ever agree with. That’s the fundamental difference.”

Leslie Cockburn

Age: 66

Resides: Rappahannock County

Occupation: Journalist, author

Grew up: Hillsborough, California

Education: Yale

Signature look: Scarves and/or a quilted green vest

Hollywood connection: Daughter Olivia Wilde and her fiancé Jason Sudeikis

Author of: Dangerous Liaison:
The Inside Story of the U.S.-Israeli Covert Relationship

Leslie Cockburn would not be running for Congress if Donald Trump hadn’t been elected president. After the first Women’s March, the former “60 Minutes” producer and “Frontline” correspondent switched teams from objective reporter to political candidate. Over the past 17 months of driving thousands of miles across the 5th District, she says she’s bought six new tires and replaced her brakes twice.

Cockburn came from money, and can drop names like Mick Jagger, who once dined in her Georgetown house. But she opted out of the country club lifestyle to which she was born, and documented her career as an investigative journalist in her book Looking for Trouble: One Woman, Six Wars and a Revolution. She says she has been the breadwinner in her family, and cares about equal pay.

Cockburn says she approached running for office as a reporter: by asking questions. “When you’re a journalist, an important part of the job is giving a voice to people who have no voice,” she says.

The number one issue she’s heard about from citizens of the 5th is health care, which affects people from the price of their insurance premiums to their ability to afford drugs to treatment for addiction and mental health issues.

Jobs are another issue for the district. “Southside has 2,500 open jobs,” Cockburn says. “One of the big reasons they’re open is because people can’t pass drug tests.” She wants to make community college free and turn the district into a jobs-producing solar-energy capital.

And she’s amassed more than 1,500 volunteers who are going door to door, as well as a $2.4 million war chest, raising $1.1 million the last quarter—compared to Riggleman’s $695,000—with $1 million cash on hand. In her latest filing, she claims 51,963 individual donors. “I’m not taking any corporate PAC money,” she says.

Cockburn cites her mileage across the 5th as the biggest difference between her and Riggleman, who started his campaign this summer. “I have been out [to places] in this district five times, 15 times. People recognize that’s essential for them to be represented.”


Cringe-worthy moments in the race

  • The Republican Party of Virginia’s ad with Cockburn’s head atop the neo-Nazi torch march at UVA, accusing her of being anti-Semitic because of her 1991 book about Israel.
  • The RPV’s “Leslie Cockburn hates America” ad
  •  Cockburn’s challenging Riggleman’s military service in Afghanistan against her own creds as a journalist, followed by husband Andrew’s tweet minimizing the risks Riggleman faced.
  • Cockburn accusing Riggleman of campaigning with an avowed white supremacist—former Jason Kessler sidekick Isaac Smith, who distanced himself from Kessler months before the Unite the Right rally and has disavowed his association with the alt-right.

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