Terry McAuliffe’s election for governor of Virginia should be a slam dunk—or at least the political pundits and pros think so. McAuliffe, of course, is one of D.C.’s consummate political pros, a prodigious fundraiser and an advisor to the Clinton family.McAuliffe has one major advantage: money. The Clinton-fundraiser has already raised a million dollars and there’s more where that came from. He’ll have a lot more to spend on the race than his opponents. But the political battlefield is littered with the remains of rich men who couldn’t buy their way into office. For example, Al Checci, the CEO of Northwest Airlines, spent millions in losing the Democratic primary for governor of California in 1998.The other two Democrats have solid political credentials. Since he is the brother of a congressman from Northern Virginia, Brian Moran should have a solid regional base and decent fundraising capabilities. Creigh Deeds, like Moran, was chairman of the House Democratic delegate caucus. In addition, Deeds has some statewide name recognition from his last race (in 2005, he lost the race for Attorney General by only 400 votes to this year’s Republican candidate for governor, Bob McDonnell). Any of these men would start the general election with an early advantage. The last two governors, Tim Kaine and Mark Warner, were both Democrats, as are both of the state’s U.S. Senators, Mark Warner and Jim Webb also are Democrats. And this year Barack Obama became the first Democratic presidential candidate to win Virginia since 1964.But Virginia voters have a history of being political contrarians. Both Kaine and Warner were elected while George W. Bush was president—and the last two Republican governors, George Allen and Jim Gilmore, were elected under Bill Clinton. If the Virginia economy is still in the tank this November, there might be a backlash against the new Democratic president.The biggest hurdle for McAuliffe may be that he was on the wrong end of the Democratic presidential primary in Virginia, where Obama beat Hillary Clinton by an almost 2-to-1 margin. You have to wonder if the good-government types who voted for a reform candidate in the presidential primary are willing to vote for a guy whose main claim to fame is raising political money for the Clintons.The other question for McAuliffe’s candidacy is whether one of the country’s best-known political operatives can morph into a public official. Making the jump will not be easy. Every time actor Jim Carey makes a comedy he brings in big money—but when he makes a drama hardly anybody shows up at the Cineplex. Jim Carey will always be a comedian; Terry McAuliffe may always be typecast as an operative.Because he is running against three old Virginia political hands, McAuliffe is running as a Richmond outsider. But he’s still a D.C. insider. The big question for McAuliffe’s campaign is which identity will win out in voters’ minds.Brad Bannon is the president of Bannon Communications Research, a political consulting and polling firm for Democratic candidates, labor unions and progressive issue groups.