Ed Gillespie, the Republican candidate for Virginia governor, poses for portraits at his campaign headquarters in Richmond. (Timothy C. Wright/For The Washington Post)

Ed Gillespie, Virginia’s Republican candidate for governor, was an hour into a campaign pitch that conservatives lap up — cutting taxes, promoting small business, opposing unions — when a hand went up a few rows back.

“What’s your opinion of Robert E. Lee?” asked Tony Lundy, 57, a welder who volunteered that he thinks the Confederate general was “honorable.”

“I appreciate your point — this is a conversation I think we need to have,” Gillespie replied, his tone as soothing as a therapist’s. But he added that he would not have that conversation then “because we’ve kept folks here for a very long time.”

Moments later, after pledging to be “an honest, ethical, hard-working, principled, faithful servant leader worthy of Virginia,” Gillespie was out the door.

Over four decades in national politics, Gillespie rose to the highest ranks of Washington’s ruling class, chairing the Republican National Committee, counseling President George W. Bush and earning millions lobbying for corporate clients seeking entree to his rarefied Rolodex.

Yet as he seeks to succeed Democratic Gov. Terry McAuliffe, Gillespie is at the center of a civil war that is dividing his party, one pitting the Republican establishment he personifies with his four-star credentials against the anti-Washington forces that propelled President Trump’s rise.

Trump lost Virginia to Hillary Clinton, and his approval rating in the state is below 40 percent. But the president’s populist appeal remains muscular enough that Gillespie has had to become a political contortionist, seeking to appeal to Trump’s base without pushing moderates toward his opponent, Lt. Gov. Ralph Northam (D).

“Ed’s a very competent, rational, thoughtful candidate who, in a more traditional Republican Party, would be a perfect fit,” said former House speaker Newt Gingrich, for whom Gillespie helped draft the 1994 “Contract With America.” “But there’s a growing level of anger about a wide range of things — a growing sense that Washington isn’t responsive. There’s a substantial minority that wants an emotional, hard-edged approach.”

Gillespie, in an interview, brushed off questions about navigating the GOP’s breach and was visibly irritated when asked about Trump. Instead, from behind his desk at his Richmond campaign headquarters, he launched into an impromptu version of his stump speech (“I care deeply about my fellow Virginians . . .”) and said pollsters and academics are more qualified to analyze the race’s dynamics.

“I just don’t have time to do this kind of punditry,” Gillespie said. “I’m just a candidate; I’m just out there talking about the issues.”

Once a ubiquitous presence on Sunday talk shows, his pointed advocacy for the GOP often leavened by genial asides, Gillespie, 56, sometimes wears the pained expression of a man trying to tiptoe through a gunfight.

His appearances — a breakneck schedule of receptions, festivals and Friday night high school football games — are carefully managed and in many cases unpublicized; his every word seems calibrated, even when responding to the most mundane questions. Asked about the political leanings of his three adult children, Gillespie said: “I’ve never asked my children what party they’re in.”

Tactical cunning has defined Gillespie’s career, beginning when he followed the lead of an early boss on Capitol Hill and switched from Democrat to Republican. Later, he worked for Republican upstart Rep. Richard K. Armey (Tex.) before joining Bush’s coterie of Washington hands.


Vice President Pence points to Virginia Republican gubernatorial candidate Ed Gillespie at the end of a campaign rally at the Washington County Fairgrounds on Oct. 14, 2017 in Abingdon, Va. (Andre Teague/AP)

On the stump, Gillespie says he is running to rejuvenate what he says is Virginia’s stalled economy, and that the next governor needs “a sense of urgency” to enact change. “I have those new policies, I have that sense of urgency, and I will not fail us,” he promises.

Affable and earnest as he campaigns, Gillespie often cites a running tally of “detailed, specific” policy plans he has released — 17 was the total one week, 18 the next, 20 in the most recent count. He tells audiences that his grandfather was a janitor and that he himself was the founder of “three small businesses,” although he omits that he is including Quinn Gillespie & Associates, a premier Washington lobbying firm that represented major corporations such as Enron and Microsoft.

As RNC chair in the early 2000s, Gillespie championed a “big tent” GOP, immigration reform and outreach to black and Hispanic voters. In his 2006 book “Winning Right,” he dismissed “anti-immigration rhetoric” as a “political siren’s song” that Republicans must reject “or our majority will crash.”

Yet as a gubernatorial candidate, Gillespie has been airing campaign ads that equate violent gangs with illegal immigrants to suggest that his opponent is lenient toward criminals. Northam’s opposition to a blanket ban on “sanctuary cities,” a narrator warns, “let illegal immigrants who commit crimes back on the street.” The ads include images of tattooed men who had been photographed in a prison in El Salvador.

Republican Ed Gillespie and Democratic Lieutenant Governor Ralph Northam are running in this year's closely watched race for Virginia governor. (Claritza Jimenez/The Washington Post)

Gillespie often refrains from mentioning Trump during public appearances. But in Danville, on the commonwealth’s south side — where turnout for Trump was robust last November — Gillespie twice promised the audience, “I will be able to work with President Trump.”

Donna Randall and her husband, George, 59, a retired power plant worker, arrived at the town hall in a minivan festooned with stickers of Trump and the Confederate flag. In Virginia’s gubernatorial primary, the Randalls backed Corey A. Stewart, the Republican who nearly upset Gillespie with his voluble defense of Confederate monuments.

“Ed’s part of the establishment,” Gary Randall said, his longish gray hair topped by a cowboy hat, explaining his support for Stewart.

“There’s a feeling he can be bought,” said Donna Randall, distributing red “Save Our Monuments” stickers before Gillespie spoke.

Later, when she asked for his views on the children of undocumented immigrants, or “dreamers,” Gillespie expressed sympathy for their plight and recounted that his father had immigrated from Ireland as a child.

Then Gillespie’s tone changed. He promised to deny dreamers in-state tuition at public universities to preserve slots for “Virginia citizens.”

“You know who should be deported?” he asked. “Someone who has been here illegally and kills somebody.”

Donna Randall applauded.

“He’s coming around,” she said.

“He’s all we’ve got,” her husband said.

‘You’re not Ralph Northam’

On a recent Saturday, Gillespie’s campaign hosted a picnic at the center of anti-Washington ferment — the countryside north of Richmond, where voters in 2014 helped catapult unknown conservative Dave Brat to an astounding upset over Rep. Eric Cantor, the House majority leader.

Hanover County voters also chose Trump in 2016 and Stewart over Gillespie in June. Now Gillespie needs their votes.

Many guests at the picnic wore hats and T-shirts bearing Trump’s and Brat’s names, and they applauded after the congressman, among the featured guests, praised Trump’s campaign to drain Washington’s “swamp.”

When it was his turn, Gillespie described Virginia’s economy as “stagnant,” promised 50,000 new jobs if his tax cut is enacted, and hailed the commonwealth as “the greatest state in the greatest country to ever grace the face of God’s earth.”

He made one fleeting reference to Trump and none to the “swamp.”

The applause were more polite than exuberant.

As Gillespie shook hands, Stuart Jones, 58, an engineer who backed Trump, Brat and Stewart, promised him his vote “because you’re not Ralph Northam.”

“Well, that’s a start,” Gillespie said.

Brat, in an interview as he ate baked beans, said that Gillespie’s challenge is to excite Republicans who became “complacent” after Trump’s victory. “We’re asleep,” Brat said. “The swamp’s still in control and we don’t have any big wins under our belt.” Asked whether Gillespie’s Washington bona fides can excite anti-establishment voters, the congressman said, “That’s what he has to answer.”

Ten days later, just before a town hall meeting on Virginia’s Northern Neck, Mal Ransone, 64, said he didn’t need Gillespie to declare fealty to Trump or defend Confederate monuments.

“What’s he going to do about the infrastructure?” asked Ransone, the owner of a construction company. His son, Andrew, 28, whose motorboat is adorned with two tall Trump flags, nodded.

“His energy should be about making the state better,” he said of Gillespie. “I like Trump, but a milder approach is better for Virginia.”

Gillespie delivered, focusing his remarks on the economy. No one asked about the president or long-dead Civil War generals.

Other issues caused awkward moments.

The evening’s final question was from a man who asked Gillespie to explain his “moral calculus” for having represented the tobacco industry when he was a lobbyist.

“Will you bring that same moral calculus to your position as governor?” asked the man, who later said he belonged to a Democratic advocacy group.

Gillespie waded into a lengthy answer in which he twice said he was “proud of my career” and three times that he was “honest and ethical.”

“You can cherry-pick clients all you want,” Gillespie said. “You could have picked Friends of Cancer Research, as well, or the Bill and Melinda Gates Foundation.

“I know how to get things done,” he promised.

Lisa Smith, 51, who was in the audience that night, had applauded when Gillespie, responding to her question, said he supported medical marijuana. But she was bothered by his tobacco answer.

“It was the whole song and dance of the politician,” Smith said. “If you made a mistake, then say you made a mistake. Or admit that you didn’t think it was wrong. Be a straight shooter.”

A talent for unity

Gillespie’s path to the Republican Party began in a Democratic household in southern New Jersey. In the dining room, his parents hung a lithograph of President John F. Kennedy, as rendered by an artist, walking in a field with Pope John XXIII.

Gillespie’s father, Jack, an Irish Catholic with a politician’s gift for banter, was a Proctor & Gamble salesman in Philadelphia before moving his family to Browns Mill, N.J., where he bought his mother-in-law’s grocery store and opened a bar.

The store was a hub of local life where Jack and Conny Gillespie expected their five children to work after school. “Even on your birthday, you’d get a cake and a four-hour shift,” said John Gillespie, Ed’s brother, echoing a line the candidate often uses on the stump.

“Eddie,” as friends still call him, displayed an early talent for illusion, able to make a dove suddenly flutter from his handkerchief, one of the magic tricks he performed as he went table to table at The Show Place, a Jersey Shore ice cream parlor. He also learned ventriloquism, encouraged by his mother who, when he was 13, bought him a dummy named “Simon Sez.” (Three decades later, Gillespie and then-Democratic Rep. Dennis Kucinich were runners-up at a “Funniest Celebrity in Washington” contest for their joint ventriloquist act).

As he headed to college, Gillespie aspired to become a political reporter, an ambition he pursued at Catholic University, where his campus sports column included “Gillespie’s Guess” — his pick of the winner for upcoming football games and grist for mockery when he was wrong.

After Catholic defeated archrival Georgetown — despite his prediction to the contrary — Gillespie ate the ink version of his words. “They crumpled up the newspaper and he washed it down with Budweiser,” said Kevin Costello, Gillespie’s housemate.

To earn money, Gillespie parked cars for Senate staff at a lot outside the U.S. Capitol, after which he interned for Rep. Andy Ireland, a Democrat from Florida who turned Republican in 1984. Although he had been raised a Democrat — “They all but stamped it on your birth certificate,” he said — Gillespie followed his boss.

“Ronald Reagan just spoke to me in a way that Walter Mondale did not,” he said.

Politics became the core of Gillespie’s existence. At a congressional softball game, he met his future wife, Cathy, chief of staff for Rep. Joe Barton (R-Tex.), who also happened to employ another person who would play an important role in Gillespie’s life — Karl Rove, then an up-and-coming consultant.

For a decade, beginning in the mid-1980s, Gillespie was a spokesman for Armey, who credited his former aide with persuading him to enlist then-Sen. Barry Goldwater (R-Ariz.) to help get national attention for what would become his signature initiative: granting Congress authority to shut military bases.

“Eddie said you need a big name,” Armey said of aligning with Goldwater. “It was a hell of an idea.”

Gillespie also helped Armey and Gingrich sell the “Contract With America,” distilling their legislative agenda into 10 points with titles such as “Fiscal Responsibility Act” and the “American Dream Restoration Act.” The contract became the cornerstone of the GOP’s 1994 revolution that resulted in the party taking control of Congress, Gingrich rising to speaker and Armey becoming majority leader.

Gillespie emerged with a reputation as a master spinmeister, though not without enduring his share of crises, including one in which he had to defend Armey for referring to openly gay Rep. Barney Frank (D-Mass.) as “Barney Fag.”

As much as anything, Gillespie was known for uniting varying factions around a central message. He resisted deviation from the party’s talking points, as pollster Frank Luntz learned during a high-volume clash in a Capitol hallway one day after he questioned language Republicans used to attack then-President Bill Clinton.

“He told me to shut up,” Luntz recalled. “He said we needed to be unified and that when a decision had been made, I needed to go along with it.”

Growing influence

By 2012, when Mitt Romney appointed him senior adviser to his presidential campaign, Gillespie’s influence extended beyond Washington.

After leading the RNC and counseling Bush, he helped mastermind a strategy that led to Republicans winning majorities in more than two dozen state legislatures, controlling redistricting in those states and ensuring that GOP candidates won House elections. The victories cemented Republican control of the House after President Barack Obama’s election.

Gillespie also helped Rove conceive of American Crossroads, a super PAC, and affiliated groups that raised tens of millions in unregulated donations known as “dark money” that Republicans funneled to GOP candidates nationwide.

“It’s fair to call Ed Gillespie one of the principal architects of ‘dark money,’ ” said Sheila Krumholz of the Center for Responsive Politics, describing him as “about as influential and connected an insider as they come.”

Yet, after Romney’s defeat, Gillespie’s friends sensed that he was fatigued and frustrated with national politics. “It was clear to me that he wasn’t going to get into another presidential campaign,” said Chris Jankowski, a Republican consultant. “He just had enough.”


Democratic candidate for governor Lt. Gov. Ralph Northam, left, shakes hands with Republican challenger Ed Gillespie after a debate at the University of Virginia at Wise in Wise, Va., on Oct. 9, 2017. (Steve Helber/AP)

Gillespie said he became fed up with life on the road, which included sleeping on a bed in the middle of a studio apartment in Boston, where Romney was based. “I missed my wife,” he said. “It’s a young man’s game.”

But he didn’t leave politics. Instead, he reinvented himself as a candidate for Democrat Mark R. Warner’s Virginia Senate seat in 2014, a campaign he said he waged because no one else would challenge the incumbent.

Gillespie lost by only 1 percent, delighting Republicans surprised by his near-upset.

“I thought I was done,” he said of his stint as a candidate.

Yet, as Virginia’s gubernatorial contest approached, the contender he supported, state Sen. Mark D. Obenshain (R-Rockingham) chose to sit out the race.

“I really thought he was going to run,” Gillespie said, adding that he then decided, “Okay, I will do it.”

Trump’s victory and the civil war within the GOP thrust Gillespie into a new tactical quagmire.

In the GOP primary, Stewart astonished Virginia’s political establishment by aping Trump’s bombast. He branded Gillespie “Establishment Ed” and nearly defeated him.

Four months later, Stewart still has not made a joint appearance with Gillespie and struggles to muster enthusiasm for his campaign, describing him as “far from the Trump model” that he believes is “becoming dominant.”

“He’s your standard Republican — a 1980s-model Republican,” Stewart recently said of Gillespie. “If Ed wins, it’s an indication that things haven’t changed that much.”

The president injected himself into the gubernatorial race in early October when he abruptly tweeted, “Vote Ed Gillespie!,” an endorsement that threw the candidate into a new round of contortions.

Gillespie did not acknowledge Trump’s support for nearly 12 hours, and only after he was asked about it on a media call. He still hasn’t included it among his long list of endorsements on his campaign website.

That afternoon, Gillespie was at his campaign headquarters desk, bristling as he faced more questions about Trump.

No, he didn’t know the president would endorse him.

No, he had not asked for Trump’s blessing.

“Can we go off the record?” Gillespie asked before saying, “I’m not going to talk about this.”

He referred further questions to his spokesman, who was sitting a couple of feet away. But Gillespie wasn’t finished.

“I don’t recall having asked anyone for their endorsement,” he said. Then: “I guess I’m just confused why this is newsworthy.”

Twenty minutes later, after the subject had changed, he circled back and insisted on one last point.

“Just to be clear, I didn’t ask him not to endorse,” he said of the president, before disappearing down a hallway.

This is the second in a two-part examination of the candidates vying to become Virginia’s next governor. The first part, about Democrat Ralph Northam, appeared Wednesday.