How in the hell did Democrats wind up struggling in the Virginia governor’s race?

Virginia is an important state. An emerging purple state. A state poised to have the kind of election-swinging clout of Ohio or Florida.

Upping the ante this cycle, Virginia Republicans, for their gubernatorial standard-bearer, have tapped the proudly inflammatory Ken Cuccinelli, who has used his reign as state attorney general to, among other notable hits, crusade against climate change and on behalf of the state’s recently junked anti-sodomy laws. For a party struggling to dispel its reputation as a bastion of right-wing nuttery, putting Cuccinelli front and center is a bit like tapping Mitt Romney to dispel the GOP’s rep as a bastion of rich old white guys.

In short, the Democrats should have had this one.

Instead, the party allowed the equally problematic Terry McAuliffe to waltz unopposed into the nomination, setting the stage for what New York magazine’s Jon Chait (capturing the sentiments of many on both sides of the partisan gulf) has dubbed the “most depressing election in America.”

With all due respect to the Macker’s many charms, he is not what you’d call an intuitive choice for governor. He has never held elective office. Despite being a longtime Virginia resident, he was unknown on the state political scene until his first, failed run at the nomination last cycle. And ... how to put this delicately ... his decades as a high-level, no-holds-barred money-grubber for the national party have given him a vaguely unsavory aroma. “He’s just sort of this shady fundraising guy most famous for the Lincoln Bedroom,” observes a veteran Virginia Democratic strategist of McAuliffe’s rep.

Trickier still, McAuliffe is one of those guys who blathers on—typically with the aim of reminding you how important and successful he is—with no sense of how he sounds to normal people. This month the chattering class has delighted in rehashing passages from McAuliffe’s 2008 autobiography, What a Party!, in which the Macker boasts at length about what an asshole he was on the occasions of his children’s births. (In one instance he skipped out on the delivery to attend a party for then–Washington Post gossip columnist and current Daily Beast editor-at-large Lloyd Grove; in another, he stopped en route to the hospital to work a fundraiser while his wife labored on in the car; in a third, he picked a political fight with his wife’s anesthesiologist.)

So it is that, for all Cuccinelli’s flaws, the superconservative AG is currently depressing voters less than the shameless hack. A Washington Post poll out this week shows Cuccinelli leading McAuliffe by 5 points among all voters and a whopping 10 points among those who say they’ll hit the polls come hell or high water.

These are, to be sure, early days. State political watchers note that few voters have engaged with the race or know anything about McAuliffe, meaning that his campaign has the opportunity to define him as the contest gains steam. Of course, so does Cuccinelli’s campaign, which is currently having a grand time hammering McAuliffe over perceived business slipperiness swirling around an electric-vehicle venture, GreenTech Automotive, which McAuliffe launched in 2009. Questions about GreenTech’s financing and incorporation and performance and taxes—not to mention McAuliffe’s decision to quietly resign the company’s chairmanship sometime late last year—are being used to chip away at his self-presentation as a proven job creator. Meanwhile, Team Terry’s lackluster response to such attacks has Dems fretting about his savvy as a candidate.

“So far, the answer to ‘How does he handle these questions?’ is ‘Not well,’” says the strategist with a sigh, and notes, “There are a lot of Democrats in the state that are getting incredibly nervous about how Terry McAuliffe is allowing himself to be turned into Mitt Romney.”

“What’s going on with Terry should be disconcerting to Democrats, not because of any damage that has been done, but because it suggests the campaign doesn’t really have their act together,” seconds a Democratic operative who does work in the state. “These are unforced errors.”

And just wait until the Cuccinelli camp starts spoon-feeding voters the unflattering bits from McAuliffe’s autobiography, warns the strategist. “Ken Cuccinelli wants this campaign to be entirely about Terry McAuliffe.”

Indeed, both sides want this race to be a referendum on the opposition, observes Larry Sabato, head of the University of Virginia’s Center for Politics. Unfortunately for Team Terry, notes Sabato, “If each makes this a referendum on the other, Cuccinelli wins by default.” Negative campaigning depresses turnout, he explains. And, in a non-presidential year, low turnout helps the GOP. Virginia’s Republican base is much more committed than its Democratic base, agrees the Democratic strategist. “Cuccinelli may be offensive to moderate and swing voters and even some moderate Republicans, but he fires up the base. He really gets its juices going. Terry’s base doesn’t have that passion. The Democratic base may like Terry at best. Some may be simply agnostic toward him.”

Thus McAuliffe is seen to have the much tougher lift. It is not enough for him to go negative and depress enthusiasm for Cucinnelli; he must find a way to actively energize Dems. “McAuliffe’s people keep stressing to me that he’s buying in to the Obama GOTV model,” says Sabato, referring to the president’s “get out the vote” strategy. Of course, he notes, that kind of voter outreach program tends to work largely for candidates like Obama who excite voters. Thus far, folks seem to agree, nothing about McAuliffe suggests he’s that kind of candidate.

That’s the bad news. Now for the worse news: If McAuliffe loses, the Dems have little hope of improving their position in the state for the foreseeable future.

The reason McAuliffe was able to effortlessly claim the nomination this time around was that the party’s farm team is embarrassingly weak. “The bench is empty,” asserts Sabato. “The only two Democrats with any state potential are in the U.S. Senate.” (That’d be Mark Warner and Tim Kaine, both former governors.)

There are only three statewide offices in Virginia—governor, lieutenant governor, and AG—explains Sabato. “If McAuliffe loses, the odds are very poor that Democrats will be elected to the other two positions unless one of the Republicans blows up."

Statewide races are expensive, in part because of the Washington media market. “Because of the cost, the money tends to concentrate in the candidate for governor, and that makes it hard to cut through when you are running for anything else on the statewide ticket,” says the operative. “Republicans are much better about trying to invest in those down ticket races.”

The Dems’ farm-team prospects are further damaged by the makeup of the state legislature, where Republicans dominate the House of Delegates—and likely will continue to do so thanks to redistricting, says the operative. Sabato agrees: “It’s a done deal until, maybe, 2021.”

All of which is to say that Dems aren’t terribly upbeat about Terry’s turning Virginia a brighter shade of blue. Offers the operative, “The only big X factor is that nothing has really started yet.”

Now there’s a campaign slogan to thrill the masses.