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Learning to do a double flip: From red to blue and from reporter to politician

Leslie Cockburn talks with Max Hall in Warrenton, Va., on Sept. 8 at an event for Fauquier County Democrats. She is navigating among progressives who want her to embrace democratic socialism and moderates who want her to win back Obama-Trump voters. (Doug Kapustin/For The Washington Post)

Knocking on door after door in Charlottesville, Va., Leslie Cockburn, making the pivot from journalist to politician at age 66, peppers people with questions: What about health care? Do you have insurance? Would you ban assault weapons?

Finally, a man on Bing Lane interrupts the Democratic candidate for the U.S. House in Virginia’s 5th Congressional District. “Tell me something you’re passionate about,” he says.

“Well,” Cockburn says, “people care about health care and the environment and racial justice.”

Two doors down, Kelly Dye also stops Cockburn’s questioning. “Tell me about you,” she says. “Why you?”

“I covered the world for ‘60 Minutes’ and ‘Frontline,’  ” Cockburn says. “Then we bought a beautiful farm in Rappahannock 20 years ago. It’s really unusual for a journalist to jump over the wall, but I did it because I feel like we’re really in trouble.”

This was never what she wanted to do. “I had no ambitions to be in politics, ever,” she said. ­Indeed, before the caucus in April in which Virginia Democrats chose their candidate in a generally Republican district that is larger than New Jersey, sprawling from the D.C. exurbs to the North Carolina border, Cockburn had booked tickets to spend this summer at her husband’s family homestead in Ireland.

“But then we won,” she said.

Cockburn was writing a novel, spending time with her grandchildren, learning Arabic and studying viticulture, thinking she might start a vineyard.

“She’s done everything: She’s written books, written scripts for movies,” said Steve Kroft, a “60 Minutes” correspondent who worked with Cockburn for many years. “I think she’s running out of things to do.”

What got her into this business was Donald Trump, specifically his coarse boasts about abusing women, as revealed on the 2005 “Access Hollywood” tape that became publicshortly before the 2016 election. Cockburn felt compelled to drop her journalistic neutrality and attend the Women’s March in January 2017. Then, after she gave a talk about fake news, friends nudged her to jump into the race against Rep. Thomas Garrett (R), whom she called “a mini-Trump.”

Garrett abruptly dropped his bid for reelection in May to seek treatment for alcoholism. Cockburn’s Republican opponent now is a fellow political novice, Denver Riggleman, who owns a distillery in Nelson County.

What is Bigfoot erotica? Cockburn accused Riggleman of being into it.

And now she has knocked on more than 5,000 doors. In a district Trump won by 11 points, she goes everywhere.

She has always been drawn to conflict. She covered six wars and a revolution for the big TV networks, “Frontline” and Vanity Fair magazine. She chased after arms merchants and scored interviews with dictators and drug dealers.

“People become journalists because they cannot decide what to be when they grow up,” Cockburn wrote in her memoir, “Looking for Trouble: One Woman, Six Wars and a Revolution.” “I started down this road as a traveler with a taste for danger.”

“With Leslie, you never know what she’ll do next,” said her husband, journalist Andrew Cockburn. “Up for any ad­ven­ture. But this is really the same thing she’s always done — satisfying her intense curiosity. Going to Cambodia to find out what’s really going on isn’t really different from going to Mecklenburg to find out what’s really going on.”

She still thinks of herself as a journalist. “I like being a critic and observer,” Cockburn said, but the times call for a new role. “As a journalist, you can expose wrongs, but you need Congress to take the next step.”

So she went to an Emerge America candidate training program in which Democratic women learn fundraising, speechmaking and networking — with a hefty dose of assertiveness training.

Cockburn had never been keen on politicians. “I certainly had an attitude that a lot of politicians weren’t thinking for themselves, that there was a blow-dried aspect to how they worked,” she said. “There were a lot of them I didn’t have time for.”

Now she’s one of them.

“It’s utter heresy for a journalist to become a politician,” said Mary-Sherman Willis, a friend of Cockburn for several decades. “She’s going to have to rein it in. This is going to be very different.”

'You need a huge tent'

Although Cockburn has worked for NBC, ABC and CBS, she was never entirely comfortable with the networks’ dispassionate style of journalism.

Rather, her most powerful work made its point of view clear. In her memoir, she blasted Ronald and Nancy Reagan’s “virulent hatred” of the Sandinista revolutionaries in Nicaragua. In her documentary on the 2008 financial collapse, she places the blame on Wall Street gamblers and their enablers in Congress.

“She’s always been a committed person, with a sense of what’s right and what’s wrong,” Kroft said.

Her friend Willis said the pre-politics Cockburn was “a little to the left of what the Democratic campaign committee would be comfortable with.”

But now, in a new role, Cockburn’s watching her words, navigating among young progressives who want her to embrace democratic socialism and moderates who want her to win back Obama-Trump voters. She’s relaxed and funny when she tells war stories about reporting in Africa and the Middle East. But her voice grows tighter, her word choices more cautious, when she speaks to voters.

At a Democratic Party crab fest in Nelson County, a young man tells Cockburn that this is the first party event he has attended and that he is disappointed. “I thought you’d be talking about how socialism is the only answer,” he says.

Cockburn is silent for a long time, then decides that however much she appreciates the young man’s passion, her campaign must, as she put it, “reach a very broad base.” Finally, she replies, “If you want to be successful as Democrats, you need a huge tent.”

Another day, asked whether she can prevail without winning back some of the president’s voters, she said, “I’m not going to woo those Trump supporters in the evangelical churches where people feel Democrats are satanic.”

Cockburn paused, then added, “We do need Republicans.”

'Going to dangerous places'

Leslie Redlich grew up in a home of Rockefeller Republicans — a lost tribe now, but one that was marked by liberal social views and a thrifty approach to budget matters.

This was San Francisco in the late 1960s, and although her parents stuck with their party — as a young girl, Leslie met Ronald Reagan — the ferment of the times called to her. She dived into the counterculture in music, politics and academics.

“Really, my politics have not changed since I was 12 years old,” she said.

She grew up rich. When she was 11, her parents took her to Japan, Hong Kong and the Philippines. She was in the second class of women at Yale Univesity. She loved arguing with her father, who made a fortune as chairman of one of the country’s largest container-handling companies.

It was, she said, “a fairly cosseted youth,” and she decided early on to break from it. “I’m not really a country club person,” she said. She moved east; her siblings stayed in San Francisco. Her brother took over the family business. She chose a different field. Not that she had a choice.

“I wasn’t asked,” she said. “I was a girl.”

She was a freshman at Yale when she signed up for her first ad­ven­ture, in Africa. Later, living in London and studying African colonial history and epic poetry, she pronounced herself “bored” and found work at the NBC bureau, where she says she “fought long and hard for the privilege of being shot at.”

Cockburn savored ad­ven­ture and had a flair for the dramatic. In her memoir, she sometimes sounds like Lauren Bacall in a 1940s noir classic: When she first met her future husband, she invited him to visit her boat on the Thames, saying, “Just go to World’s End and head for the river.”

As a reporter, Cockburn would travel for weeks at a time. After her children were born, when friends asked whether she really wanted to be so far from home, she turned the tables on them: “While people often ask me if I am worried about leaving my family, no one has ever asked Andrew that question,” she wrote.

“I knew she was going to dangerous places,” said her eldest child, Chloe Cockburn, now 39 and a lawyer and criminal justice reform advocate in New York. “Whenever my mom was home, she always made time to read us bedtime stories. But she didn’t hide from us that she might not come home from one of those trips.”

Once, during one of those readings from a Roald Dahl novel or a Curious George book, Chloe asked her mother, “What happens if you both get killed?”

The practical answer was that the Cockburns had a plan in place — and a will in the hands of their lawyer.

“We’ll be fine,” Cockburn told her daughter.

'We dressed for dinner'

She has hosted Georgetown dinner parties where the diplomat Richard Holbrooke sat on one side of her and Mick Jagger on the other. She’s had dinner with Saddam Hussein’s sons and tea with Moammar Gaddafi. She wrote a screenplay with the daughter of novelist William Styron.

Although Cockburn has had a house in the Rappahannock horse country for 19 years and made it her primary residence 11 years ago, it’s her Georgetown home that her critics tend to focus on. (She also bought an $800,000 apartment in Brooklyn when her daughter Chloe was trying her hand at being an artist in New York.)

Cockburn and Riggleman tangle over residency in first debate

Republicans have sought to paint her as an elite outsider whose connection to Virginia is that of a weekend visitor.

“This is a culturally conservative district,” said John Findlay, executive director of the Virginia GOP. “She is not really in tune with the district culturally.”

Cockburn pushes back hard: “It’s not like I’m some lady on a horse farm,” she said. She says she has lived in the district far longer than her opponent has.

Cockburn’s D.C. connections have come in handy. This summer, she held a wine-tasting fundraiser in Georgetown, hosted by the renowned D.C. chef Nora Pouillon, where guests were invited to donate $2,700 a head. Cockburn has raised almost three times as much money as her opponent.

Her younger daughter, the actress Olivia Wilde, best known for her roles in TV’s “House” and the film “Tron: Legacy,” adds another dash of celebrity to a family that has long led an A-list social life.

In Georgetown, Cockburn has been a regular in the society pages. But Kevin Chaffee, the editor of Washington Life magazine and a longtime friend, has visited the Cockburns in Rappahannock frequently and said it’s been their primary home for many years.

“Her great grandpappy didn’t fight for the South in the Civil War,” he said, “but she’s spent more time there than Hillary ­Clinton or Bobby Kennedy did in New York.”

Cockburn’s writing has fueled her critics’ argument that she is a visitor from a different class. In her memoir, she described her son, Charlie, as being born “after the sorbet and blackberries at the end of a long, leisurely lunch party.” Even when she was covering conflicts in some of the globe’s roughest places, she carved out time for evenings with wealthy hosts where, as she wrote, “We dressed for dinner.”

The New York Times called Cockburn’s memoir “a troubled book” that was “tone-deaf” about her wealth.

Cockburn’s elder daughter rejected the idea that her mother is a dilettante. “What that question about elitism is really about is, ‘Do you have skin in the game?’ ” Chloe said. “Yes, she comes from a wealthy family, but we grew up on journalists’ salaries. She’s literally put her life on the line. She could have retired. She doesn’t need this.”

Criticism on Israel

As soon as Cockburn was nominated in May, Virginia’s Republican Party attacked her as a “virulent anti-Semite.” John Whitbeck, then the party chairman, called Cockburn “the inspiration for neo-Nazis, white supremacists and racists.” (Whitbeck, who has since resigned from his post, opened a GOP rally in 2013 with an anti-Semitic joke.)

The Republican argument is based entirely on their reading of “Dangerous Liaison,” a scathing 1991 book about ties between U.S. and Israeli policymakers that Leslie and Andrew wrote together.

The book was immediately ­controversial.

“It oozes sardonic anger that mutual interests often bring the United States and Israel together,” said a review in the Miami Herald. The New York Times deemed the book “largely dedicated to Israel-bashing for its own sake.”

“They stubbornly hear what they want to hear,” the Los Angeles Times’ critic wrote. “Still, there is no denying the Cockburns’ point that Israel has weakened its own moral case by longtime liaisons with brutal dictators and shady operators.”

“The book blames the Jews for everything,” said a top state GOP official who spoke on the condition of anonymity because he was not authorized to speak for the party. But when asked for examples of Cockburn’s anti-Jewish sentiment, the Republican said he had found nothing beyond the book.

After the allegations first received attention, Cockburn met for two hours with 40 Jews at the home of Rabbi Daniel Alexander, for many years the leader of Congregation Beth Israel in Charlottesville.

He concluded that “the book insufficiently gets what Zionism is all about and why the mainstream of the Jewish community has an attachment to Israel despite the policies of its current government.”

But he said Cockburn clearly supports Israel as a Jewish state and would have no problem voting for aid for the embattled country. “The majority of the people at the meeting were satisfied,” Alexander said.

Cockburn finds the allegation exasperating. “In a whole year here, no one has asked me about a foreign policy issue,” she said.

Yet she still defends the book and remains critical of Israel’s ­government and Prime Minister Benjamin Netanyahu. “We need to be allowed to say these things,” she said. “Whatever Netanyahu wants, he gets. That’s not good for Israel in the long run.”

The allegations, along with President Trump’s popularity in the district, have made some Democrats uncertain about investing in her campaign. The Democratic Congressional Campaign Committee has decided to pump money into more than 100 House races this fall. Cockburn’s is not one of them.

“I’m arguing to them that they should really look at Leslie,” said Sen. Tim Kaine (D-Va.), the state’s former governor. “The noise about anti-Semitism is the Republicans trying to distract attention from their own connection to extremists in Charlottesville. Writing a book critical of U.S. and Israeli foreign policy is not anti-Semitism.”

GOP tries to tie Cockburn to white nationalists at Charlottesville

Guns vs. health care

When Cockburn was growing up, her mother owned a ranch in California where Leslie and her parents hunted for ducks, pheasants, deer and moose.

“There were always guns in the house,” she said.

This comes up on the campaign trail often. Cockburn tells Virginians who are skeptical of her liberal views that where she lives in Rappahannock, “we have to shoot deer because otherwise they’d be in our bed.”

Still, the doubts are palpable. A girl at a 4-H Club meeting asks when Cockburn’s “going to take away our guns.”

Cockburn replies, “This is Virginia; we don’t do that.”

But she’s also quick to tell voters that “the idea of having assault weapons in the hands of untrained people is absurd.”

In Charlottesville, Cockburn knocks on the door of a man who is inclined to vote for her but is wary of her support for a federal ban on assault weapons.

“I am a gun owner and I don’t like to vote for people who want to take them away,” he says.

“Most people voting for me have guns,” Cockburn replies. “Obviously, we protect hunters. But let me ask you, how do you feel about assault weapons? Ban them?”

“No,” the man says. “But I’ll make you a deal: I would turn my guns in if we had universal health care. You get that, and you can have my guns.”

The man accepts a lawn sign. An hour later, at a Flip the Fifth rally, Cockburn tells the story of the man who would trade his guns for health care. The crowd loves it.

She’s learning.

This is the first of a two-part look at the candidates running in Virginia’s 5th Congressional District. Tomorrow: Denver Riggleman.