Ed Gillespie, foreground, walks through the Chesterfield County Fair while greeting voters with Del. M. Kirkland Cox, right , in white shirt. (Bill O'Leary/The Washington Post)

Call it Campaigning 101.

Republican Ed Gillespie had it down, shaking hands with his right, handing out palm cards with his left and smiling all the while like there was no place he’d rather be on a sweltering August evening than the 101st Chesterfield County Fair — and nothing he’d rather be doing than touting his “five-point plan for economic growth.”

“If you like what you see, I’d love to have your vote in November. Enjoy the fair,” Gillespie said, moving from table to table in a pavilion. At one point, he tried to turn down a cup of Italian ice, hoping to keep his hands free. It didn’t work.

Like many before him, Gillespie, a longtime GOP strategist and former lobbyist, appears to have made the transition to candidate for public office.

But Gillespie — who is running as much as 25 points behind Sen. Mark R. Warner (D) in recent polls — chose an uphill battle for his first race, a decision he has in common with lots of politicians, including Warner and Virginia Gov. Terry McAuliffe (D). And just like other operatives who ran as long-shot aspirants, Gillespie has much to gain even if he loses in November.

Ed Gillespie, center, greets voters with Del. M. Kirkland Cox, right, at the Chesterfield County Fair. (Bill O'Leary/The Washington Post)

After announcing his candidacy in January, Gillespie quickly began honing his skills on the campaign trail, building a network of donors and raising his name recognition. The experience could serve him well, because there’s always the next time. For Gillespie, another big statewide opportunity isn’t that far off: the 2017 governor’s race.

Gillespie denies that he has his eye on the 2017 race, but in the meantime, he’s poised to step into the role of de facto leader of the Virginia GOP, which lacks any statewide officeholders. The state party is bitterly divided along the lines of a national rift between establishment moderates bent on taking control of the U.S. Senate and grass-roots conservatives fed up with incumbents and frustrated by the ways of Washington.

Gillespie briefly united the two sides when he handily won the state GOP nomination for the Senate seat in June, apparently convincing tea party activists and members of the country club set that he’s one of them.

Ed Rollins, the campaign strategist who managed President Ronald Reagan’s 1984 reelection campaign, said even if this race doesn’t go Gillespie’s way, he’s far from finished.

“No one ever goes into the race saying, ‘I’m going to lose.’ Often, you learn lessons,” Rollins said. “Ed has always had the ambition to do something big in Virginia. Whether he makes it this time or next time, he’s going to be senator or governor one day.”

Unlike Rollins — who said he decided when writing his first attack mailer at age 19 that “no one’s ever going to do this to me” — some political operatives can hardly wait to see their names on the yard signs once they see how the game is played. Others take a more measured approach. But one way or another, political careers generally begin behind the scenes and off the ballot.

On the Democratic side, Bill and Hillary Rodham Clinton worked on George McGovern’s 1972 presidential campaign. Chicago Mayor Rahm Emanuel, who was President Obama’s first chief of staff, had much-less-important staff jobs before he ran for and was elected to Congress. Maryland Gov. Martin O’Malley (D), who is contemplating a 2016 presidential campaign, worked for Gary Hart’s White House bid and for Sen. Barbara A. Mikulski (D-Md.).

Ed Gillespie, center, greets voters at the Chesterfield County Fair. (Bill O'Leary/The Washington Post)

On the Republican side, Dick Cheney, who famously recommended himself to be George W. Bush’s running mate, worked in the Nixon and Ford administrations, including a stint as White House chief of staff, before being elected to Congress. And Haley Barbour had a long career as a political operative, including four years as chairman of the Republican National Committee, before mounting a successful campaign for Mississippi governor.

“That was something I was a little bit nervous about, but it really worked out well,” said Henry Barbour, Haley Barbour’s nephew and the strategist who ran his uncle’s campaign. “As you might expect, early on, Haley laid out strategic objectives, but he let us run the campaign, and he didn’t try to ­micromanage the campaign.”

Two Virginia politicians are prime examples of political operatives who experienced defeat during the transition to elected official. McAuliffe, who was a former chairman of the Democratic National Committee, a prolific fundraiser and President Clinton’s best bud, was trounced in the 2009 party primary for governor by state Sen. R. Creigh Deeds (D-Bath). But he came back strong four years later.

Warner ran L. Douglas Wilder’s gubernatorial campaign in 1989, and he was head of the state Democratic Party before he lost to then-Sen. John W. Warner (R) in 1996. Mark Warner came back five years later to win the governorship, and he cruised to victory in the Senate election in 2008 after John Warner decided to retire.

Bob Holsworth, a retired Virginia Commonwealth University political science professor, said seeing the ups and downs of a campaign from behind the curtain makes former operatives more resilient as candidates.

“They know they lose one, they go to the next. You can lose not because you’re inherently terrible or inept. They think, ‘Maybe I can adjust something,’ ” Holsworth said.

Gillespie’s lack of experience as a candidate is occasionally visible. He used notes and garbled a few answers in his first debate with Warner last month. And although he had a hand in developing the “Contract with America” that helped make Rep. Newt Gingrich (R-Ga.) the House speaker, his efforts at branding this year — he’s got an “EG squared agenda” and an “Ease the Squeeze Tour” — may not catch on quite so well.

Gillespie said he relishes his new role. “This may sound a little odd to you, but what surprises me is how much I love being the candidate,” he said. “I like being out there, talking to people, listening to people, hearing what their concerns are [and] standing up for what I believe in.”

At the Chesterfield fair — squarely in Republican territory in suburban Richmond — Sam Galstan, a dentist from Fairfax County, said he sees Gillespie’s insider status as a plus.

“I think you need a certain amount of inside access to know how the game is played,” he said, standing near a chicken-on-a-stick booth. “I think sometimes we send people up who are true outsiders and they don’t know the process and they are very ineffective.”

One challenge that political strategists have is presenting themselves as people of conviction, a potential vulnerability that Democrats have seized on in Gillespie’s case. They have labeled him a hired gun.

“These folks are often the masters of spin and very adept at adjusting their positions to whatever the positions of the candidate are or the circumstances of the time,” Holsworth said. “People want to see what you’re passionate about, what really moves you.”

In TV ads paid for by the Virginia Progress PAC, Democrats have portrayed Gillespie as an insider without conviction. The ads call Gillespie “everything that’s wrong with Washington,” describe him as “out for himself, not you” and point to his work as a lobbyist for the infamous Enron.

And Democrats have made an issue of Gillespie’s stand on abortion. He said in a recent interview that he does not support a proposed constitutional amendment to grant fetuses 14th Amendment protections, or “personhood.” Warner’s campaign said the RNC platform included the “personhood amendment” when Gillespie was chairman.

After Gillespie breezed by Chris Bishop’s picnic table at the fair, Bishop, 54, said he was turned off by the Democrats’ ads. “He was a very successful lobbyist,” Bishop said. “A lot of people put a bad connotation on lobbyist. Well, they’re not going to get rid of lobbyists. That’s the way this country works, and we need somebody who’s successful.”

Bishop’s wife, Linda, 52, remained skeptical.

“I have some more research to do,” she said. “Anybody can smile and shake hands, but I want to see the unbiased facts.”

Perhaps the best evidence that Gillespie is playing a long game is his mostly positive message. Until a recent partial attack ad drew a strong connection between Warner and Obama, Gillespie had avoided harsh language that can turn voters off.

“You’ve got to come out the other end with people saying, ‘He ran a solid campaign; he’s a good guy,” said Quentin Kidd, a political scientist at Christopher Newport University. “You can’t come out the other end saying, ‘He came close, but, man, was that nasty.’ ”