But what he has been loathe to emphasize -- in a reflection of this anti-establishment, anti-moneyed moment -- is his ties to a Republican super PAC that, for all its riches, presents a political predicament to candidates running for high office in the first year of Donald Trump's presidency.
Slowly and quietly, Gillespie has shed his high-powered connections to the group that he helped found, American Crossroads, ignoring some of its elite donors and forging a new political identity as he stares down a Republican challenge eager to highlight Gillespie's role unleashing the modern campaign-finance system that Trump says he deplores.
While campaign aides push back on his role in the formation of Crossroads, describing him as an adviser -- not a founder -- his work ushering in this period of American politics is difficult to ignore.
It's led to an unusual dynamic: A super PAC founder running in one of this year's marquee races who is largely not taking advantage of the big-money system that he helped pioneer.
Candidates have long sought to publicly play down their connections to wealthy donors in favor of a cracker-barrel profile that endears them to regular voters. But the politics are perhaps never so obvious as they are at this moment, led by a president who has often bellowed to the country that today's donors are corrupting and unseemly.
"All political money these days is a liability," said Ed Rogers, a Republican lobbyist close to Gillespie who nevertheless advises him to cash all the checks he can get. "Net-net, take the money."
One senior Crossroads fundraiser predicted that GIllespie would soon capitalize on his rich friends -- pointing to a Gillespie finance event hosted by Bush this month in Dallas
where traditional Crossroads donors cut him a check.
And Gillespie aides say that the candidate has never shied away from those funders. Aides argue that during his run for Senate in 2014
, few believed he had what it took to topple the popular Sen. Mark Warner. At that time, Gillespie was virtually unknown in Virginia and Warner had won statewide by handsome margins on two different occasions.
Despite his gravitas with donors, he struggled to collect money.
Even when the polls tightened late in that race, Gillespie fundraisers pitched donors for an injection of cash that never came. He and his outside groups ended up being outspent by more than three-to-one -- but he lost the race by less than a percentage point.
Gillespie's candidacy is much different this time around, though he has once again not been able to take full advantage of his connections to a network of rich donors. One of his opponents in the GOP primary, though, believes it is only a matter of time.
"Ed Gillespie is a 30-year revolving door lobbyist," said Corey Stewart, the former chair of Trump's campaign
in the state and who is running in his mold, "desperate to hide the fact he made millions peddling influence as a Washington insider using government to enrich himself."
The chair of the Prince William County Board of Supervisors, Stewart has relentlessly attacked Gillespie's deep ties to Washington, tagging him with the moniker "Establishment Ed." But so far there is little evidence that Stewart's attacks have been effective: The most recent poll, conducted by Christopher Newport University, shows Gillespie with a healthy lead among the three candidates on the ballot.
Super PACs, though, are broadly unpopular in today's political climate: Gillespie never mentions Crossroads on the stump, and his official biography makes no mention of it.
And after all, Gillespie is not wanting for funds. Former Mississippi Gov. Haley Barbour, a former business partner of Gillespie's and once a Crossroads fundraiser himself, predicts that in a general election -- with Democrats eager to nationalize the race into a referendum on Trump's presidency -- the donor network he helped cultivate will eventually come home.
Yet a survey of a dozen recent Crossroads donors this week revealed numerous major givers who say they have surprisingly not heard from Gillespie, even though some would gladly cut him a check should he call.
"He's been a friend for a long time," said Mel Sembler, a major Republican fundraiser. But Sembler hasn't given -- he "absolutely" would if asked, though.
"Who is he again?" asked media mogul Stan Hubbard, a Crossroads giver who said he deals mostly with former Bush aide Karl Rove, not Gillespie.
Gillespie may be discovering that just because Republican donors have funded Crossroads, it does not mean that they will fund him personally.
"Ed's relationship is with more the staff, princples and leadership with Crossroads -- and not neccssarily with the rank-and-file-donors," said one person close to the group, granted anonymity to candidly assess the relationship.
Gillespie's intimates and multiple people close to Crossroads concede that his ties to the organization have long withered, Immediately after the Citizens United decision upended politics in 2010, Gillespie worked hand-in-glove with Rove to launch a batter of Republican fundraising operations that could allow the GOP to capitalize on the erasure of contribution limits.
Since then, however, Gillespie's role has drastically diminished at Crossroads, according to multiple people familiar with the inner workings. Much of the Rove's political operation at Crossroads has been subsumed by that of Mitch McConnell, who has blessed the Crossroads network and launched a new partner organization, Senate Leadership Fund, that gobbled up much of the establishment Republican money in the 2016 race. After McConnell's team held the Senate against tough odds, some predict Rove's role could weaken even more.
Nevertheless the donor network that Gillespie built at Crossroads is largely absent from his current run, according to an analysis of Virginia campaign finance disclosures. Donors to Crossroads -- such as Home Depot founder Bernie Marcus or new Trump Cabinet members Linda McMahon and Betsy DeVos -- are responsible for just over $350,000 to Gillespie's gubernatorial political operation, $100,000 of which came solely from the DeVos family.
One longtime Crossroads donor, St. Louis billionaire Rex Sinquefeld, met with Gillespie twice since he announced his run for governor, according to Sinquefeld aide Travis Brown, and Sinquefeld admired his commitment to cutting taxes. But Gillespie failed to draw a check out of him, according to campaign finance records.
Yet several senior Republicans close to Gillespie and Crossroads predict that the network's donors will eventually come around, arguing that prominent conservative givers won't tolerate a loss in the high-profile off-year election. And for now, sources concede, it's better politics to focus on Virginia givers -- not high-wattage GOP billionaires, who are almost all from out of state.
"After talking to a number of Crossroads donors," said the senior group fundraiser, "I'm confident many are in his corner."