Democrat Terry McAuliffe, left, and Republican Ken Cuccinelli, right. (Associated Press/Getty Images)

Many of the most generous donors to past Virginia Republican campaigns are holding back in the heated race for governor, underscoring Attorney General Ken Cuccinelli II’s challenge as he tries to keep financial pace with opponent Terry McAuliffe.

Cuccinelli (R) is specifically having trouble luring many of the key contributors who backed the 2009 bid of Gov. Robert F. McDonnell (R), according to an analysis of the most recent campaign-finance records. For months, Cuccinelli has lagged in fundraising behind McAuliffe (D), a businessman with a long history of raising millions for the Democratic National Committee and Bill and Hillary Rodham Clinton.

Through May, Cuccinelli has raised nearly $4 million less than McAuliffe and $3.3 million less than McDonnell had at the same point in the 2009 gubernatorial contest. Although Cuccinelli has prevailed in races in which he was outspent by opponents, his fundraising deficit is a significant obstacle in what is likely to be a prohibitively expensive campaign.

McAuliffe has promoted the narrative that some Republicans, particularly in the business community, are gravitating to the Democrat because they are leery of Cuccinelli’s opposition to the new state transportation funding plan and such social issues as abortion and same-sex marriage. Democrats contend that his views in those areas could prevent the state from attracting companies and skilled workers.

Although several Republicans agree that Cuccinelli’s positions have contributed to his campaign’s financial shortfall, especially in Northern Virginia, only a handful of high-profile GOP contributors have defected to McAuliffe. Many more donors have simply chosen to sit on the sidelines. For now, at least.

More Post coverage of the race for Virginia governor.

Bobbie Kilberg, the president and chief executive of the influential business group Northern Virginia Technology Council, said supporters are “still assessing” both candidates.

“I think the business community has not yet engaged on this race, and they’re waiting to see how the candidates develop their positions,” said Kilberg, a close ally of McDonnell’s who has accused Cuccinelli of being overly concerned with social issues. “I’ve most definitely noticed a real holding back.”

The donor scale

Election Day is still four months away, but Cuccinelli has ground to make up. He had raised $6.5 million through the end of May, compared with McAuliffe’s $10.4 million.

According to a Virginia Public Access Project analysis, as of May 29 Cuccinelli had gotten contributions from 14 percent of the same itemized individual donors who gave to McDonnell’s campaign through May 2009. Less than 1 percent — nine out of 1,505 — had donated to McAuliffe, while the rest had given to neither candidate.

At the top of the donor scale, Cuccinelli picked up five of the 20 contributors who had given $25,000 or more to McDonnell and 27 of the 85 who had kicked in at least $10,000 at the same point in the 2009 race.

Cuccinelli campaign strategist Chris LaCivita scoffed at the notion that the Republican was in a weak financial position.

“Comparing our fundraising to Governor McDonnell’s, who had the benefit of being the Republican nominee eight months longer than Ken, is like comparing apples to bowling balls . . .” he said. “Of course, we expect to be outraised by Terry McAuliffe, who has made a career of cashing in political chits, landing sweetheart deals and making promises to union bosses and contractors. At the end of the day, Ken will win this campaign based on a stronger, forward-thinking message and authentic grassroots support across Virginia.”

Still, several Republicans and industry people said they believe that Cuccinelli’s opposition to the Silver Line rail to Dulles project and this year’s landmark transportation billMcDonnell’s signature achievement — could affect his fundraising.

“I’ve never seen the business community as united as they were” on the transportation measure, said Clayton Roberts, president of the nonpartisan business group Virginia Free.

One Northern Virginia business executive who donated to Cuccinelli this year said some of his fellow Republicans are wary of the attorney general.

“All they know is the law-and-order and social stuff, and he scares” them, said the executive, who spoke on the condition of anonymity to speak frankly about the candidate. He added that some donors with legislative interests in the state worry that Cuccinelli is “unlobby-able.”

One of McDonnell’s biggest contributors — Ted Weschler, a Berkshire Hathaway portfolio manager — has given only to McAuliffe’s campaign, while Dominion chief executive Thomas F. Farrell II has made small donations to both McAuliffe and Cuccinelli.

Then there is Dwight Schar, chairman of the home-building company NVR and a Washington Redskins minority owner, who gave $70,000 to McDonnell’s campaign and also kicked in six figures to the governor’s political action committee. Schar endorsed McAuliffe in early June and has attacked Cuccinelli for his “ideological agenda” and “focus on extreme social issues.”

Some donors from the financial sector also may have been dissuaded by SEC rules to limit “pay to play” practices. The guidelines restrict contributions to state and local campaigns by firms and investment advisers that do business with public pension funds.

Fred Malek, a major Republican donor who is co-chairman of Annapolis-based Thayer Lodging Group, said he could not personally contribute to Cuccinelli because “the new rules make it very difficult for a private-equity managing partner to give money to a statewide race.”

But, Malek added, “I support Ken Cuccinelli to the hilt.”

Waiting for the bandwagon

Polls have shown the race to be tight, and Cuccinelli could still enjoy a late windfall if momentum looks to be on his side in the final months leading to Election Day.

Some of McDonnell’s most generous donors in 2009 waited until October to contribute, when it was clear he had the advantage. McDonnell had raised $9.8 million through May 2009 and ended up raising $24 million for the contest.

“If people believe you’re going to win, they want to be with the winner,” said Boyd Marcus, a Republican campaign consultant who has worked for Lt. Gov. Bill Bolling.

Some well-known conservatives, including retired Roanoke Realtor Lynn Via and energy billionaire David Koch, have stood by Cuccinelli. And Cuccinelli has managed to attract some deep-pocketed supporters who did not give to McDonnell four years ago, among those, hedge fund executive Sean Fieler.

Fieler, the chairman of the American Principles Project, a conservative advocacy group in Washington, said he donated $50,000 to Cuccinelli’s campaign because of what he called “McAuliffe’s extreme position on abortion.”

Cuccinelli has excelled with small donors: Through May, he had gotten about 12,000 donations of $100 and under; McAuliffe received fewer than 8,000. LaCivita said the Republican had gotten more than “16,000 individual contributions” since the end of May and “almost three times the number of contributions at this point in the race compared” with McDonnell in 2009.

Some of McDonnell’s donors were longtime Democrats, including Sheila Johnson. The co-founder of the Black Entertainment Television network caused a stir by endorsing and donating $50,000 to McDonnell four years ago. This time around, she said, she will be voting for McAuliffe — but doesn’t plan to contribute to either candidate.

“I’m not giving nobody another dime,” Johnson recently told The Washington Post. “I’ve spent way too much money on politicians. . . . It’s like throwing money down a toilet.”