On Thursday, two days after Bolling returns to the commonwealth, he will announce whether he will rejoin the contest he quit in November, coming back as an independent.
His reentry would be an act of considerable political daring for a Republican loyalist who four years ago put his plans to run on hold for the sake of party unity. It would also shake up the race to succeed term-limited Gov. Robert F. McDonnell (R), with Bolling aiming to position himself as the middle-of-the-road alternative to two polarizing major-party candidates: one a tea party hero, the other a Bill Clinton pal.
Bolling was still undecided when he left for his trip and was considering all of the factors, the biggest of them money, according to an adviser who spoke on the condition of anonymity to freely discuss private deliberations. Up until he boarded the plane Tuesday with his wife, Jean Ann, Bolling was making phone calls to potential donors, the adviser said.
Bolling could not, by law, raise money during the 46-day General Assembly session that concluded Feb. 23. Since then, he has had time to feel out “a sampling” of potential benefactors to see if he could raise the $10 million to $15 million he would probably need.
“You can’t call 200 people, but you can call 30 people,” the adviser said. “Every campaign is a step into the dark, to a certain extent. You don’t know everything until you start running the race.”
With Bolling away — he has been declining all requests for interviews and is said to be checking e-mail just once a day — Republicans and Democrats back home are left guessing about his next move.
The presumptive major-party nominees — Attorney General Ken Cuccinelli II (R) and former Democratic National Committee chairman Terry McAuliffe — are clearly wondering whether they’ll face one opponent or two. But they are not saying much publicly.
“Regardless of what happens on Thursday, Terry will continue to talk about the economy and mainstream ideas to make the Commonwealth better for business,” McAuliffe spokesman Josh Schwerin said in an e-mail. Cuccinelli’s campaign declined to comment.
There is intense interest among Republican and Democratic activists, particularly on the GOP side, where people are split over whether a Bolling run would help the party or destroy it.
Bolling dropped out of the race for the Republican nomination in November after Cuccinelli supporters managed to switch the nomination method from a statewide primary to a closed party convention. The latter format was expected to greatly favor the attorney general, since conventions are dominated by conservative party stalwarts.
Some moderate and even conservative Republicans believe that Cuccinelli, who has waged high-profile battles against the federal government, a university climate scientist and abortion rights, is too far to the right. For them, a Bolling run would present a more moderate image of the party because, while long conservative on most issues, he has a more pragmatic, conciliatory style.
But other Republicans fear that Bolling would divide the party and hand the governor’s mansion to McAuliffe. Democrats are privately cheering that possibility, but some fear Bolling could split the anti-Cuccinelli vote and wind up hurting McAuliffe.
There are Republicans who have been begging Bolling to stay out out of the race, including C. Daniel Clemente, a Tysons Corner lawyer and real estate developer who helped orchestrate someone else’s independent bid in 1994.
Upset that Iran-contra figure Oliver North had secured the GOP nomination for U.S. Senate, Clemente helped former Republican attorney general Marshall Coleman run against North and incumbent Charles S. “Chuck” Robb (D). Coleman finished a distant third.
“We ended up with 14 percent of the vote,” Clemente said. “And that was a monumental effort, with a very popular candidate, with strong backing in the conservative community and among moderate Republicans. . . . So when I met with Bill Bolling, I said, ‘Please don’t run as an independent. The only thing you’re going to do is hand the election to Terry McAuliffe.’ ”
Clemente said he likes Bolling but questions how hard he would work as a candidate and as governor, given that he did not do more to beat back Cuccinelli supporters as they worked to pull off the primary-to-convention switch.
“Cuccinelli was working out in the open, and Bill was coasting,” Clemente said.
Yet there are others who say they’d be willing to write Bolling big checks if he jumps in.
“He would have an enormous appeal to a lot of people who don’t like the extreme left and the extreme right, and that has been the story of Virginia politics,” said Earle Williams, a retired defense contracting executive from Northern Virginia.
Williams, who put $2 million of his own money into a failed bid for the GOP gubernatorial nomination in 1993, has assured Bolling supporters that he would offer financial support to his campaign. Williams said he thought it was important for Republicans to have an option besides Cuccinelli — someone he says he understands far less than his own primary opponent, George Allen.
“I could understand George’s positions on things even if I didn’t agree with them,” he said. “I just don’t understand Cuccinelli. . . . Cuccinelli represents, as far as I’m concerned, an outlier.”
Williams added: “I may have that completely reversed — I’m the outlier, and he’s the mainstream. I guess that’s what we’re going to find out.”