A bit past 5 o’clock on a mid-September Wednesday, one month after the miraculous resurrection of his moribund Senate campaign, Jim Webb comes busting out of Call Room One, where Democratic candidates are held captive for hours at a time and forced to plead for cash. Catching the eye of his “body guy,” former Marine Corps Times editor Phillip Thompson, Webb barks, “We’ve got to be in Alexandria, don’t we?” The former Navy Secretary’s feet, shod in combat boots belonging to his son, Jimmy, who’s just gone on active duty in Iraq, never stop churning as he pushes through the heavy front door of the Democratic Senatorial Campaign Committee’s Washington headquarters and pounds down the narrow walk-up toward his ride–a small SUV, painted in camouflage, with a Jim Webb–Born Fighting sign fixed to the side. Behind the wheel, as always, is “Mac” McGarvey, who lost an arm in Vietnam under Webb’s command. When his “best friend” decided last February to challenge Virginia’s wildly popular Republican Senator, George Allen, Mac up and left his job running a bar in Nashville, volunteering to spend the next nine months being directed–and misdirected–all over the interstates and backroads of Virginia.

“I have no idea where we’re going,” Mac says as Webb bounds into the front seat, quipping, “That could be taken as a symbolic statement about this campaign.” After haggling with the body guy over the best route to his after-work campaign rally, Webb props a boot up on the dashboard and calls over his shoulder, “We have a live at 5:25?”

“There’s a live at 5:40.”

“All right. Oh, man. Do you have the binder with the speech in it?” The body guy hands it up to Webb. “I’m sorry,” the candidate calls back to me. “You can ask me questions in a minute. I don’t have a speechwriter, and I just wrote this this morning, and I need to go over it.” It’s impossible to tell whether Webb, who’s congenitally deadpan, is kidding about the speechwriter. He speed-scans the copy, scribbling a few lines in the margins and handing back a page at a time to the body guy, who’s quietly pointing Mac toward Alexandria. When they get there–if they get there–Senator Barack Obama will be there, too, making his first pitch for a former member of Ronald Reagan’s Cabinet. It will also, no doubt, be Obama’s first endorsement of a formerly bitter critic of Vietnam War protesters, civil rights activists, 1960s liberals, affirmative action policies and women in combat–just a few of Webb’s targets through the years.

From a cranky Republican traditionalist, Webb has transformed into one of the unlikeliest protest candidates ever. And now, thanks to the spiral of controversy set off by Allen’s now-legendary “macaca moment” in mid-August, Webb has also become the unlikeliest of this year’s Democratic challengers to have a genuine shot at toppling a Republican incumbent and giving his new party a majority in the next Senate.

Webb’s gonzo campaign–chaotic, underfunded and featuring a candidate who refuses to pander or even, at many campaign appearances, to so much as crack a smile–grew out of his exasperation with Allen’s unwavering support for George W. Bush’s Iraq adventure. Webb had been warning against military intervention in Iraq, insisting that it would destabilize the Middle East and spawn dangerous anti-Americanism, since the late 1980s. After he wrote an op-ed in September 2002 predicting US invasion forces would “quickly become 50,000 terrorist targets,” Webb met with the senator–whom he had endorsed over Democrat Charles Robb in 2000–to discuss his concerns. Webb came away with his dander up, disgusted by Allen’s reportedly insisting, “You’re asking me to be disloyal to my President.”

Webb might have been a hellacious soldier–one of the most highly decorated to return from Vietnam, in fact–but he has never been a go-along guy, to say the least. His stint as Navy Secretary, for instance, ended with Webb abruptly resigning after just ten months, protesting the Reagan Administration’s refusal to fully fund the 600-ship fleet he insisted was necessary. But as mad as he was about Iraq, and about Allen’s automatic approval of Bush’s disastrous policies, Webb took his sweet time deciding whether to challenge Allen’s re-election bid. It would mean abandoning his lucrative writing career, which has included six critically acclaimed war novels, a successful Hollywood screenplay (Rules of Engagement) and a bestselling cultural history of the Scots-Irish in America (Born Fighting). It would also mean having to do things the proud and contrary Webb despises–like begging for money. When he finally took the plunge, it was with high hopes the candidacy might “inspire some intelligent debate” on the war. Webb had also decided he could help “reshape American politics” by showing how a Democrat can combine foreign policy “realism” with an old-fashioned dose of economic populism to win in the South again.

“I think both parties have been taken over by elites,” Webb says over his shoulder after he’s done perusing his speech. “The natural base of the Democratic Party, working-class folks, looked at both parties and saw they weren’t going to get any more help on economic issues. The one place they thought they could make a difference was on these divisive social issues, so that’s how they’ve been voting. But I think that has run its course now.” So, he says, has the “cultural Marxism” of the 1960s that’s dominated the Democrats. “We’re in a sea change with political terminology and identities,” he says. “What is right and what is left anymore? What is conservative and what is liberal?”

With his mix of “foreign policy realism, economic populism and social moderation”–Webb is prochoice and staunchly opposed to the anti-gay marriage amendment on the Virginia ballot this November–he aims to put a crack in the Republicans’ recent dominance of federal elections in the South. His challenge is not only to the GOP but to national Democrats and “Yankee liberals” who have increasingly abandoned hope of competing in the South. “This race is a test,” Webb says. “If we can get a number of these people to come back to the Democratic Party based on economic populism and fairness, rather than the way they’ve been maneuvered on issues like flag-burning, God, guts, guns, gays–if they can be reached out to with respect, and in terms of fundamental fairness, I think a lot of them will come back to the Democratic Party.”

It seems fitting that if he’s going to win on November 7, Virginia’s newest fightin’ Democrat will have to beat a champion practitioner of the Republicans’ faux-populist Southern Strategy. Often viewed as the second coming of Ronald Reagan, George Allen has mastered the art of convincing working-class voters he’s a regular guy while carrying water for big money. The Southern California native’s blend of Disneyesque optimism, easy-going geniality and tough-guy talk have made him–as a state legislator, congressman, governor and US senator–one of the most popular figures in Virginia history. “He’s always been a very smooth, on-message politician,” says longtime observer Mark Rozell, professor at George Mason University and co-editor of The New Politics of the Old South. “Allen had a natural touch for the political that could disarm some of his worst enemies, with that nice smile and charm. And he seemed incapable of making a mistake on the campaign trail. It was no surprise that conservatives were seeing him as their best presidential option for 2008.”

But in just fifty-nine seconds on the second Friday in August, Allen’s veneer cracked. It happened, not coincidentally, in the “Reagan Democrat” stronghold of southwest Virginia, where Allen had deployed “moral” wedge issues to rack up nearly a 2-to-1 margin over Senator Robb in 2000, more than enough to cement his victory statewide. At a small rally in Breaks Interstate Park, Allen was amiably plying his stock of platitudes, promising to “run this campaign on positive, constructive ideas.” Then Allen spotted the lone audience member of color, Webb campaign volunteer S.R. Sidarth, a 20-year-old Fairfax native of Indian-Asian descent who’d been following Allen on his summer “listening tour,” videotaping his remarks. Jabbing an index finger in Sidarth’s direction, Allen said, “This fellow over here in the yellow shirt, Macaca or whatever his name is, he’s with my opponent–he’s following us around everywhere.” Allen flashed his fans a broad, mischievous grin. “And it’s just great. We’re going to places all over Virginia, and he’s having it on film.” Allen swiveled back toward Sidarth. “You show it to your opponent [sic], because he’s never been here and probably never will come.”

In his suddenly awkward way, Allen was sticking to the tried-and-true Southern Strategy script, attempting to paint his Democratic foe as an out-of-touch elitist. Rather than communing with the everyday people of southwest Virginia, he said, Webb “actually right now is with a bunch of Hollywood movie moguls.” (Webb was in Los Angeles for a fundraiser.) In contrast to his highfalutin literary opponent, Allen said, “We care about facts, not fiction. So, welcome–let’s give a welcome to Macaca here. Welcome to America, and the real world of Virginia.”

By nightfall, Allen’s remarks were burning their way across the World Wide Web and reviving long-held suspicions about the Senator’s racial views. As a state legislator, Allen had voted against Virginia’s Martin Luther King Day. As governor, he issued a proclamation honoring Confederate History Month, asserting that the Civil War, far from a slavery dispute, was “a four-year tragic, heroic, and determined struggle for independence, sovereign rights and local government control.” In the 1993 gubernatorial campaign, Allen’s lifelong passion for the Confederacy–symbolized by the rebel flag displayed in his living room and the noose he’d hung up in his law office–raised eyebrows but did not prevent him from using religious wedge issues to win a surprisingly high slice (as much as 17 percent, according to one poll) of the African-American vote. Once in the Senate, he relied on symbolic gestures–a well-publicized “civil rights pilgrimage” to Alabama, a formal apology for slavery that he co-sponsored–to foster the illusion of racial moderation.

So much for that illusion. “We’ve always thought George Allen was racially insensitive,” says John Boyd Jr., president of the Virginia-based National Black Farmers Association. Allen didn’t help matters, especially among working-class voters who like a “stand-up guy,” when he subsequently claimed he’d invented the word “macaca” on the spot. He stumbled over questions about his mother’s roots in French Tunisia, where “macaca” is a common racial slur.

In a September address to a national conference of black educators, Allen–a professional politician for nearly thirty years–said he’d learned a “valuable lesson about the power of words.” Reverting to a familiar campaign theme–in which he scores cultural points by reminding folks that his dad, George Allen Sr., was the longtime Los Angeles Rams and Washington Redskins football coach–the beleaguered Senator cooked up a bizarre explanation for why he never learned to respect racial sensitivities. “On football teams and every team sport, you don’t care about someone’s religion, race or their ethnicity,” he said. “All you care about is if that person can help your team.” The color-blind racial utopia of football, Allen went on to say, is precisely what “we should aspire for in our society here in America.”

A few weeks later on Salon, three of Allen’s former football teammates at the University of Virginia accused him of having used the word “nigger” with some regularity during his college days–claims echoed by well-known Virginia political pundit Larry Sabato, another classmate of Allen’s at UVA. Allen flatly denied the accusations, saying, “It is not who I was and is not who I am.” But even the old teammates who remembered him fondly also remembered that his affection for country music and the Confederacy had led them to call him “Neck,” short for redneck.

Now, it seemed, everybody in Virginia–everybody in America–was buzzing about George Allen’s racism. Everybody except his opponent.

On the third Sunday in September, Jim Webb got what looked like the second big break of his campaign. In a Meet the Press face-off, host Tim Russert joined Webb in dogging Allen about his unflagging support for the Iraq War. Webb’s incisive critique of the war and his call for an ambitious “diplomatic process” that would include Syria and Iran sounded mighty appealing next to Allen’s grinning recitations of White House talking points. When he squared off with Allen the next afternoon at a Chamber of Commerce debate in Fairfax, Webb intended to build on his Meet the Press momentum and make the campaign–finally–a referendum on the war, and on GOP mistreatment of the middle and working classes.

Instead, the debate was only just warming up when Allen suffered yet another “macaca moment.” When local TV reporter Peggy Fox asked where the Senator had learned his now-infamous racial slur, Allen launched into a defense of himself and his family, noting among other things that his mother’s father, Felix, had been incarcerated by the Nazis during World War II. He should have left that last part out. Fox had read a recent article in The Forward alleging that Allen was trying to hide his family’s Jewish heritage, and she asked him if the allegation was true. The question jolted the normally unflappable Allen, who visibly recoiled while his half of the audience jeered and hooted the reporter. “Why is that relevant–my religion, Jim’s religion, or the religious beliefs of anyone out there?” he demanded. When Fox stoutly replied that she was seeking “honesty, that’s all,” Allen angrily defended his honor, insisting, “I was raised as she was, as far as I know, raised as a Christian.”

Throughout it all, Webb stood stock still, gazing straight ahead, expressionless as a grunt at roll call. When his time came to comment, Webb managed only to mumble a few words about how he didn’t see why Allen’s religion mattered. And the next day, when Allen admitted in a written statement that his mother had indeed revealed to him, a month earlier, that her family was Jewish, Webb remained as lock-lipped as he had through the whole “macaca” controversy.

Campaign-watchers viewed Webb’s strange silence as another sign of his stubborn resistance to behaving like a proper politician. “The ‘macaca’ fallout softened up George Allen for the kill,” says Mark Rozell. “Webb doesn’t seem to know how to plunge the knife in.”

But Webb’s reticence is not simply the product of poor politicking–or a noble refusal to sling mud. Webb has troubles of his own with the same issues that have caused Allen’s stumbles. During his Democratic primary campaign last spring, Webb was accused of anti-Semitism after his campaign put out a cartoonish flier depicting his opponent, Harris Miller–a longtime corporate lobbyist–as “Miller the Job Killer,” a big-nosed, cigar-puffing “anti-Christ of outsourcing.” (Miller now says he’s convinced that his former opponent is “not an anti-Semite.”)

Far more problematic for Webb’s campaign–especially in a state where nearly a fifth of the voting-age population is African-American–is his history of bashing affirmative action. The most notable example is a Wall Street Journal book review in 2000, where Webb wrote: “Affirmative action, which originally sought to repair the state-induced damage to blacks from slavery and its aftermath, has within one generation brought about a permeating state-sponsored racism that is as odious as the Jim Crow laws it sought to countermand.” When questions came up during the primary campaign about Webb’s startling assertion that racial “preferences” were as damaging to society as segregation itself, Webb tried unsuccessfully to argue–as he does at length in Born Fighting–that affirmative action should be based on a history of economic deprivation, not simply on race. But he also said, somewhat confusingly, that he believes African-Americans should be the sole beneficiaries of affirmative action programs, not members of other ethnic groups.

As a result, says civil rights activist and Virginia Commonwealth University professor W. Avon Drake, potential black voters don’t know what to make of Webb. “He went a little too far in changing his position,” Drake says. “Blacks can sense when someone is genuine.” When word got around that Webb had addressed Confederate descendants at the National Confederate Memorial in 1990, asserting that Southern soldiers believed they were fighting for “sovereignty rather than slavery,” some black Virginians could only conclude that there was scant difference between the two white candidates for Senate. “I look at the race and I see two Republicans running for the same job,” says longtime State Senator Benjamin Lambert of Richmond, who stunned his colleagues with a late-August endorsement of Allen, who had promised to help Lambert win more funding for traditionally black colleges.

Lambert’s endorsement will carry little weight statewide, especially given the avalanche of racial embarrassments for Allen’s campaign. In a Mason-Dixon poll taken in early September, just 5 percent of black Virginians said they would support Allen this time. But only 73 percent said they’d vote for Webb–well below the usual mark for Democrats running statewide. Webb’s campaign has yet to be endorsed by the state’s most powerful black Democrat, former governor and current Richmond Mayor Doug Wilder, and it’s faced criticism all along for failing to reach out aggressively to black leaders and voters. But in late September Webb met with the black legislative caucus and made the rounds with respected black leaders like Ray Boone, editor of the state’s largest black newspaper, the Richmond Free Press. Boone has his doubts about Webb, but his paper has taken Senator Lambert to the woodshed for equating Webb’s shortcomings with Allen’s. “The bottom line is that we need to send a strong message that the George Allen type of politics is intolerable and unacceptable,” Boone says. “He has built a career on racist campaigns.” When November rolls around, says Drake, “Webb will get 90 percent of the black vote. The question is how many votes there will be.”

“I am fired up!” Barack Obama shouts from the stage in Alexandria. “I need some help in the Senate.” And Jim Webb’s help, Obama says, is just the kind he wants. “I’ve had enough of politicians who act tough on TV,” he declares. “I want somebody who really is tough.” Together, Obama promises, he and Webb will work toward the kind of “practical, nonideological, honest and trustworthy government the American people deserve.”

Under the pure blue sky of this late-summer afternoon, with a big, diverse crowd wearing Webb stickers and cheering lustily, the messy crosscurrents of the year’s strangest Senate race seem far away. Even Webb, who breaks into more than one smile during the proceedings and hugs Obama happily when it’s over, seems momentarily carried away by the giddiness of a campaign that is, out of the blue, looking like a winner. A little more than a month before, Webb had been a forgotten candidate, trailing by double digits in the polls and facing an ominous 15-to-1 fundraising deficit. The prominent national Democrats whose endorsements had put him over the top in the primary were nowhere in sight. Democratic campaign committees, busy pouring millions into “key” non-Southern states, had coughed up a grand total of less than $40,000 for Virginia as of July–not only shutting out a compelling antiwar candidate but ignoring the fact that the Old Dominion has become so competitive in recent elections that pollster John Zogby has dubbed it “the new Ohio.”

Now that Webb is neck-and-neck with Allen in the polls, the money’s coming in–however belatedly. So are the rock star Democrats: John Edwards and Hillary Clinton, among others, would soon follow Obama’s lead. The Illinois Senator’s appearance was calculated, of course, to ratchet up enthusiasm for Webb among black voters. But his unqualified embrace of Webb will also help here in northern Virginia. With its booming population of left-leaning nonnatives, northern Virginia is the main reason Virginia has become, in pundit Sabato’s terms, a “purple state.” To beat Allen, Webb will need an overwhelming margin of victory here to offset the votes of “moral conservatives” elsewhere–especially since the Republican still has at least one ace in the hole.

Named for its Christian-right co-sponsors, the Marshall-Newman amendment is expected to draw droves of evangelical Virginians to the polls. Allen, meanwhile, is expected to spend a sizable portion of his campaign war chest on ads portraying Webb’s opposition to the measure as proof that he’s just another amoral, elitist liberal. But it might not be the silver-bullet wedge issue Allen is looking for. That’s partly because Virginians don’t like to mess with their Constitution, whose declaration of rights is the world’s oldest such document. It’s mostly because the amendment–vaguely worded and sure to prompt a spate of lawsuits if it passes–has the broadest reach of any yet proposed.

“What’s really amazing, as compared to your garden variety gay-bashing, is the breadth of its application to opposite-sex couples,” says Michael Schewel, former Virginia secretary of commerce, who’s been speaking against the amendment to business groups. “The only thing it doesn’t affect is gay couples,” because state law already prohibits them from marrying or enjoying spousal benefits. After an initial paragraph defining marriage, the rest of the amendment prohibits all “unmarried individuals” from exercising any “rights, benefits, obligations, qualities or effects of marriage.”

“This is nothing but a divisive wedge issue to get their people to the polls,” says Charley Conrad, president of Virginia Partisans Gay and Lesbian Democratic Club. But where other states’ amendments have merely been summarized on their ballots, the full text of Marshall-Newman will be there for Virginia voters to read–thanks to the efforts of amendment opponents like Governor Tim Kaine, who pressed for a state law requiring the full amendment to appear. “Our slogan ought to be, Read the whole thing,” Schewel jokes. Polls show that most Virginians who do read the amendment are confused–and opposed.

If gay marriage is supposed to be Allen’s ace–along with the millions his campaign has to spend on attack ads–Webb might yet trump him with his unblemished record of opposing the Iraq War. In Virginia, like everywhere else, disgust with the war cuts across partisan, racial and cultural divides. “Black people know the war is not making life better,” says Ray Boone. “It’s diverting resources abroad. It’s killing our people.”

Bush’s war is no more popular in predominantly white southwest Virginia–at least not on a recent Saturday in Castlewood, where hundreds gathered for the annual fish fry and political rally of the United Mine Workers’ local. “We think it’s useless,” says Jimmy Taylor, a young truck driver. “Why send more people in to get killed?” Taylor’s girlfriend, Brittany Brading, agrees. “Bush is sending all this money to Iraq when people are homeless and hungry here. It’s disgusting.”

In the heart of George Allen’s “real world of Virginia,” this year’s fish fry mostly turned into a rally for Jim Webb. Southwest Virginia generates about one-third of the state’s votes, and cutting into the Republicans’ normally large margins of victory here was key to this decade’s elections of successive Democratic governors, Mark Warner and Kaine. Webb just might do the same. While Allen has his wedge issues, he can’t match the depth of Webb’s connection to these folks–or his understanding of the reasons that many of them have strayed from the Democratic fold.

Like practically every 60-year-old white person with roots in southwest Virginia, Webb was born into a blue-collar clan of ardent Democrats. As he came to political consciousness in the 1960s, Webb grew offended by the attitude civil rights activists–“liberal Yankees,” in particular–took toward working-class whites in the South. “The fight over ending legal racial segregation,” he writes in Born Fighting, “ended up demonizing people who had shared the same social and economic dilemma as the blacks themselves.” The venom should have been directed, Webb believes, at the small class of wealthy Southern (and Northern) whites who had always controlled Dixie’s economy and insured the continuation of Jim Crow. When he came back from Vietnam, Webb was equally dismayed by the cold shoulder returning soldiers received from those who opposed the war. It was enough to send him scurrying, along with a growing number of white Southern Democrats, into the waiting arms of the GOP.

“I was generally comfortable with the Republicans, until the neoconservatives took over,” Webb says. “But the one issue that always bothered me was economic fairness.”

In Castlewood Webb heeds his own advice to Democrats: Respect the voters you’re addressing. His speech is virtually identical to the one he gave in “liberal” northern Virginia–right down to the Marx and Engels references–and carries precisely the same message: Bush and Allen’s war is a disaster, and working Americans are getting shafted while corporations and CEOs rake in record profits. One thing’s different here, though: Webb’s laconic delivery, far from a liability, testifies in shorthand that he’s no slick politician. Which makes him a far cry from his opponent, says Sam Church, UMW local’s political coordinator. “Allen doesn’t relate to working people–has he ever had a job?”

Perched in a lawn chair nearby and clutching his cane, Robert Ervin–who left the mines in 1979 after thirty-eight years–doesn’t mince words. “George Allen? He’s the nearest nothing ever been in this country. He’s a big old fake, that’s all.” If enough Virginians end up agreeing with that assessment, Allen will be in a heap of trouble on November 7. And for all his lack of political panache–in fact, partly because of it–Webb will have pulled off something few thought possible: making the Republican in a Southern race look like the one who’s unreal, elitist and out of touch with regular folks.

For a lot of Virginians, it’s been looking like that ever since Labor Day. The holiday doubles as the state’s annual kickoff for election seasons, and it’s long been obligatory for politicians running statewide to appear in the big Laborfest Parade in Buena Vista, not far from the Blue Ridge Parkway. This year was a little different. Jimmy Webb was about to ship out to Iraq and his dad, the antiwar candidate, decided to skip the biggest political day of the year to say goodbye.

“Everybody had heard where Webb was that day, and why,” recalls Charley Conrad. “So people are standing there watching the parade, and what do they see coming down the street but George Felix Allen, in a big white ten-gallon hat and those fancy boots he always wears, grinning and waving from atop a brown-and-white horse called–I’m not kidding–Bubba. And all I could think was, I sure hope people are paying attention.”