RICHMOND, Va. — Ed Gillespie has been in plenty of tight spots during his three decades in and around politics.
A Washington insider well accustomed to the public eye, he’s helped sell a military surge in Iraq to a war-weary public, stood up for a doomed U.S. Supreme Court nominee his own political party didn’t like, and lobbied for corporate clients with serious popularity issues, like Wall Street banks and Big Tobacco.
Now he’s facing a challenge of a much different kind: running for governor of Virginia as the establishment Republican nominee in the age of President Donald Trump.
Gillespie is not only trying to overcome a fractured base of support in an increasingly liberal state, but also trying to navigate the fallout from an unpredictable president who is unpopular overall in Virginia but still has strong support from voters crucial to a Gillespie victory. Adding pressure, Virginia is one of only two gubernatorial elections this year and as a swing-state, and could serve as an early referendum on the president.
Trump’s near-polar opposite in style and temperament, Gillespie has responded by running a discordant campaign. He has simultaneously tried to excite Trump supporters with sharp-elbowed ads on immigration and Confederate statues, while also appealing to the more moderate electorate with a focus on taxes and other pocketbook issues.
The approach may work: most polls show Gillespie in a tight race with Democrat Ralph Northam, but Gillespie’s approach has been criticized by Democrats and even some Republicans as insincere.
“I feel sorry for him, being in the position he’s in,” said Sam Wright, a retired state worker from Goochland, after listening to Gillespie at a candidate forum.
Pity is not an emotion usually associated with Gillespie, a New Jersey native who grew up helping in his parents’ grocery store and graduated from Catholic University in Washington before working as a congressional aide. He rapidly rose to become one of the top GOP operatives in the country and made several lucrative trips through Washington’s revolving doors.
Highlights from Gillespie’s lengthy resume include helping Republicans craft the Contract with America in the 1990s, being chairman of the Republican National Committee and serving as a White House adviser to President George W. Bush. Gillespie helped usher Bush’s Supreme Court picks through the nomination process — including the failed bid of Harriet Miers — and played a key public relations role in Bush’s efforts to increase troop levels in Iraq.
Gillespie then oversaw a massively successful effort to help Republicans win control of statehouses in 2010, and helped advise Mitt Romney’s 2012 presidential bid.
Along the way, he became a multimillionaire as a lobbyist and consultant. Gillespie started a lobbying firm with a prominent Democrat, quickly became a top player in the influence game and made millions selling his stake in the company. He took a break from his work as a consultant to blue-chip clients to run for Senate in 2014, a mostly under-the-radar contest against heavy favorite Sen. Mark Warner that Gillespie almost won.
Longtime friends and colleagues praise Gillespie as a deft communicator with a deep understanding of policy who hasn’t let professional success change him.
“Ed is a genuinely positive person and that’s just a huge advantage,” said former House Speaker Newt Gingrich.
On the campaign trail, Gillespie largely maintains a sunny disposition and has skipped Trump-like rallies in favor of more subdued events, with lengthy policy discussions and G-rated language.
“I’ll be danged if my generation says, ‘Hey sorry, it’s the end of the line,'” Gillespie said at a recent campaign stop in Norfolk when talking about his promises to enact pro-growth economic policies. It was about as animated as he gets on the stump.
But the Gillespie on TV, social media and on mailers is much more aggressive, promising tough justice on unlawful immigrants who commit crimes in similar tones to how Trump successfully campaigned. One Gillespie mailer blasts Northam for supporting driver’s licenses and in-state tuition for “illegals” — a pejorative term that’s a marked departure from Gillespie’s longtime advocacy that the GOP be more welcoming to minorities and avoid the “political siren’s song” of anti-immigrant rhetoric.
When asked about the mailer, Gillespie spokesman Dave Abrams said Gillespie had directed his campaign not to use the term in the future. Gillespie has defended his hard-hitting immigration ads as consistent with his past stances, saying his goal is to target unlawful immigrants who often prey on other members of the immigrant community.
Corey Stewart, who Gillespie narrowly beat in the GOP primary, praised Gillespie for moving to the right on cultural issues, but said Gillespie still needed to fully embrace Trump and his message.
“He’s improving,” Stewart said. “But there’s still more work to be done.”