More than a decade before he laid plans to leverage his credentials as a Republican mega-lobbyist and fixer into a Senate bid in Virginia, Ed Gillespie mapped out a very different political blueprint in nightly meetings convened over Chinese takeout in Philadelphia.
It was 2000, and then, as now, the electoral stakes for Republicans were high — and the party pinned its hopes and resources on Gillespie's success. Gillespie was part of a small team organizing the Republican National Convention, four critical days that would give candidate George W. Bush his best chance to win over voters and complete his transformation from Texas governor to presidential nominee.
The planning group was hand-picked by Andrew Card, a close Bush adviser who later became White House chief of staff, and Gillespie was Card’s first choice to engineer the convention program, from choosing the speakers and celebrity surrogates, to approving the music and the staging.
Gillespie's work broke with convention tradition to spice up and diversify a famously staid event, traditionally staged less for the public than the party faithful. It would be remembered as a resounding, seminal success — and would help propel Gillespie to the highest Republican ranks.
“The [Republican] Party in general and the public had no idea who did it,” said Jim Nicholson, who then led the Republican National Committee, “but a lot of the insiders in the party really sat up and took note of this guy Gillespie who put it all together.”
“That convention,” Nicholson added, “was the place that really launched him.”
The arc from aide to elected office, which Gillespie will try to complete this year by challenging Sen. Mark Warner, D-Va., is a beloved trope in Washington. Gillespie’s path has been distinctively long.
In a story fit for a stump speech, Gillespie, 52, born to an Irish Catholic family in New Jersey, got his start as a Senate parking lot attendant before he spent more than a decade as a House aide — ultimately shaping the “Contract with America” that in 1994 helped win a House Republican majority.
Today, after a streak as a lobbyist, campaign adviser and political gamesman, Gillespie has cemented a reputation as a respected sage in the modern Republican establishment, a go-to fixer for strategic puzzles of all shapes. But Gillespie’s transition from aide to candidate was neither seamless nor immediate.
In early 2000, Gillespie edged toward becoming a “principal,” Washington jargon for a power broker, when he started the lobbying firm Quinn Gillespie & Associates with Democrat Jack Quinn. Although the firm marked a bold career move for Gillespie, it wasn’t enough on its own to make him a major Republican figure.
“Quinn Gillespie showed him as a principal, but the convention made him a respected political leader,” said John Feehery, a Republican strategist who has known Gillespie since they worked as House aides. He's an executive with the firm, now called QGA. “That was a real turning point in his career.”
During the first planning meeting, Gillespie “was surprised to learn that not a single [speaker] had yet been invited,” he wrote later in his book, Winning Right.
The convention was “less than six weeks away, and not a single singer, not a single speaker, not a single person to recite the Pledge of Allegiance had been lined up yet,” he wrote. “We had our work cut out for us.”
During nightly meetings at the convention center or in a nearby hotel, Gillespie, Card and their colleagues gradually mapped out the convention.
Scraps of paper, filled with discarded ideas, piled up.
Card began by listing 100 words people chose to describe Bush favorably, and 100 more words used to criticize him. The favorable words would frame the convention, and Gillespie would take the program from there.
"I ran some things by [the Bush campaign] and made sure I was moving in the right direction," Gillespie said, "but I had a lot of latitude to make decisions."
Gillespie decided on an aggressively modern convention to portray Bush as "a different kind of Republican," with everything tailored to a primetime television audience. The tedious roll call of states, when delegates formally cast their votes for a nominee, would be staggered to make it more dynamic. And Gillespie brought the stage closer to the audience to put the politicians and delegates on equal footing.
Most controversially, Gillespie insisted that speaking slots — traditionally reserved as plum platforms for lawmakers, candidates and party officials — be shortened to allow for more speakers, and then doled out liberally to non-politicians.
“Everyone wants prime time on that podium at the convention, but they’re not all going to get it,” Nicholson said. “Ed was sensitive to all of the different egos that are involved,” handling them with “congeniality and firmness” characteristic of his style.
Among the speakers was Windy Smith, a 26-year-old woman with Down syndrome, who read a letter of support she had written to Bush. Gillespie also selected the professional wrestler Dwayne "The Rock" Johnson to banter onstage with then-House Speaker Dennis Hastert, a former high school wrestling coach.
Other minor moments hinted at an Ed Gillespie production.
When the hard-edged former first lady Barbara Bush appeared onstage during the convention’s second night wearing a blue dress, the song “Devil With A Blue Dress On” introduced her. The choice was daring, and it was Gillespie’s call.
During the convention, Gillespie celebrated his 39th birthday at an Irish bar. But the party continued to toast him long after the convention adjourned.
“The convention allowed him to earn more respect even from people who were cynics or skeptics,” Card said. “[Ed] was seen as smart, creative, and outstanding at understanding the audience that had to hear our message but who might not be paying attention.”
Gillespie’s recollections are less effusive. "I think people thought I’d done a good job," he told the Washington Examiner. But, in later conventions, the model he created would become standard.
When Bush won the election, the incoming administration peppered Gillespie with entreaties to join the White House as legislative affairs director. Gillespie worried a White House post would keep him from spending time with his young children, and he declined.
"I felt that I had responsibility at home that I had to meet," Gillespie said.
He returned to his lobbying firm, occasionally offering advice whenever the White House asked.
It was a lucrative decision. As a lobbyist, Gillespie is said to have joked to his former boss Rep. Dick Armey, “ 'Dick, I make more money by knowing you than you make by being you.' ” (The remark has evolved in Washington lore, and it is a matter of dispute whether Gillespie made the point about himself or someone else.)
But, in 2004, Gillespie agreed to accept a position much closer in salary and job description to Armey’s, when Bush asked Gillespie to lead the RNC.
In signing on as RNC chairman and in running for Senate, Gillespie's rationale was consistent. "If you believe in certain things, and you have the opportunity to serve, and you can serve, then you should step forward," Gillespie said. "I’ve tried to do that when circumstances allow for it."
If there was relatively little money to be earned, there were other payoffs. During the presidential election, Gillespie traveled the country making hundreds of appearances, honing his skills as a public figure. As an aide, he had written speeches; now, he was delivering them.
Gillespie left the RNC a fully formed political figure, thereafter maintaining his lobbying business and then working in the White House — before turning his focus to Virginia, where he lives with his wife, Cathy.
Gillespie made an intentional entrée into Virginia politics in 2009 as chairman of Bob McDonnell's successful gubernatorial campaign, but he says he did not consider running for office until now. In Card's telling, "It grew over time to something that he could see as a reality.”
But Gillespie faces steep odds, and Democrats are eager to use his biography against him, including his lobbying career and his ties to Bush. Meanwhile, Warner, the well-funded Democratic incumbent, remains well-liked in Virginia.
"The more Virginians get to know Washington lobbyist Ed Gillespie, the less they're going to like him," said Justin Barasky, a spokesman for the Democratic Senatorial Campaign Committee.
Should Gillespie lose, he could be well-positioned to wage another campaign, such as for Virginia governor in 2017. Reverting to a behind-the-scenes operator, however, is not an option. For Gillespie, now an established force in his own right within the Republican Party, that moment has passed.
"I think I’ve been an effective advocate for other people," Gillespie said, "and it occurred to me that if you can do that for other people, you can do that for yourself."