There was a time, not so long ago, when Jim Webb was supposed to be exactly what the Democratic Party needed. Webb gave a strange and stumbling performance in the Democratic presidential debate on Tuesday night, his final flourish being a somewhat off-topic quip that he killed a man. He was an odd fit on stage, championing gun rights and asking why poor whites weren't included in diversity programs. “I believe that I am where the Democratic Party traditionally has been,” Webb said. He’s kind of right! Webb is like a weird mirror reflecting back Democrats’ fairly recent past—including Hillary Clinton’s.

Webb's moment as the It Guy was in 2007, not long after he was sworn in as a senator from Virginia. He'd been in office a minute, delivered a rousing State of the Union response, and was already being floated as a possible veep. That year, GQ marveled that “a white, southern, gun-toting, decorated Marine, a man who for thirty years had mostly contempt for liberal America, became one of the shining stars of the Democratic Party and the ideal running mate for Barack Obama or Hillary Clinton.” Webb, who'd been President Reagan's Navy Secretary, offered solid national security credentials as well as “access” to the votes of “downscale, culturally conservative whites."

After six-and-a-half years of President Obama, it's weird to remember that fairly recently this formula was thought to be a path to success for Democrats nationally. But liberals were lost and confused under George W. Bush. “I still want to be the candidate for guys with Confederate flags in their pickup trucks,” Howard Dean said in 2003. He did not succeed. "We in Europe like John Wayne, we liked him in cowboy films. We don't like him running the world,” Piers Morgan said of Bush the same year. It turned out Americans did.

After Bush’s re-election, Democrats were consumed with self-loathing. They hated the Middle Americans who rejected them, but they also wanted those Middle Americans to love them. Just before the election, New York had suggested that New York City should secede. (Author Jennifer Senior nominated Donald Trump to be the city’s ambassador to America.) Afterward, a map dividing the country into Jesusland and the United States of Canada went viral even though social media didn’t really exist, and so did a single-serving site displaying a rant called “Fuck the South.” Post-mortems were filled with inwardly directed disgust. Thomas Frank wrote “Why They Won” in The New York Times; Democrats had abandoned economic populism, he said, and “imagined themselves the ‘metro’ party of cool billionaires engaged in some kind of cosmic combat with the square billionaires of the ‘retro’ Republican Party.” John Kerry's war record had been touted as part of his appeal in 2004, but then he'd let himself be portrayed as a wimp anyway. Sensitive, nice-person public radio figure Ira Glass aired a rant about how Kerry should “just go away.” Glass confessed, “When I'm flipping channels, and I see him making a speech, or giving an interview, I feel this moment of rage, actually. … I see him, and it's like seeing some ex-girlfriend that you don't want to run into on the street.”

How could Democrats grow big and strong and win back America's heart? Demographic trends looked bleak, the Los Angeles Times reported: “new long-term population projections from the Census Bureau show that anyone who believes Democrats can consistently win the White House without puncturing the Republican dominance across the South is just whistling Dixie.” (The demographic tables have turned.) Democrats concluded “their party must speak in language familiar to, among others, the disaffected hog farmers of Missouri,” the New Yorker reported in May 2006.

Then along came Jim Webb, and a crew called the "Redneck Caucus." Webb had served in Vietnam. He’d been a Republican. He'd opposed the Iraq War but in this super-cool, tough-guy way. He had a campaign aide named Mudcat. Webb had written a book, Born Fighting: How the Scots-Irish Shaped America, about how his ancestors had stood up to tyrants of all sorts. GQ reported, “odd and romanticized as it sounds, Webb believes he came to Washington to represent the Scots-Irish, or at least their modern-day heirs.” The senator told Virginia voters he would “bring more people back into the Democratic Party. … People who will understand the basic message of what I call Jacksonian democracy, and that is that you measure the health of your society not at its apex but at its base."

That sounded nice enough, but it seems pretty clear Webb was only interested in one slice of that base. (The white slice.) As Anderson Cooper noted in the debate, Webb said in 2000 that affirmative action "has within one generation brought about a permeating state-sponsored racism that is as odious as the Jim Crow laws it sought to countermand." On guns, Webb said at the debate that mentally ill people shouldn’t have access to them, though "we have to respect the tradition in this country of people who want to defend themselves and their family from violence.” For good measure, he repeated an NRA talking point: that government officials have bodyguards 24/7, so why shouldn’t the average American be able to protect himself? Asked about Black Lives Matter, Webb said “every life in this country matters.” (Though: “I have had a long history of working with the situation of African Americans.") On climate change, he said he was “an all-of-the-above energy voter.” 

And then, at the end, when asked which of his enemies he was most proud of, Webb said, “I’d have to say the enemy soldier that threw the grenade that wounded me, but he’s not around right now to talk to.” The line did not land well. Maybe because it was a decade too late. 

In retrospect, Webb's 2006 Senate race did foreshadow the future—just not as it looked then. His Republican opponent, incumbent George Allen, had faltered after using an odd racial slur that was filmed by a young tracker for Webb and posted online. At the time, Webb was thought to have triumphed by speaking the language of working-class whites. But in reality, his victory—and the votes of Missouri's Claire McCaskill and Montana's Jon Tester—was due to big margins in the cities. Webb performed no better in rural Virginia than less-macho Democrat Tim Kaine had in the gubernatorial race in 2005.

Today, it's clear that liberals did not have to change. They had to wait. It wasn’t new ideas that fixed Democrats’ problems. It was demographics, and a cultural shift in their direction. In between the era of Nascar angst and this election is the Obama administration. But the bridge between the old view and the new one is Hillary Clinton. 

In 2006, the New Yorker warned, “Since the Lyndon Johnson landslide of 1964, only two Democrats have won the Presidency—both moderate Southern governors.” One of those was Clinton’s husband, of course. He had an accent and wasn’t fancy. He left the campaign trail to execute an intellectually disabled man. He passed welfare reform and the 1994 crime bill. He lectured rappers on race relations.

In Tuesday's debate, though, Hillary Clinton highlighted her proposals that would undo some of her husband's signature legislation, including his draconian 1994 crime bill. She talked about “reforming criminal justice,” saying “we need to tackle mass incarceration.”

In 2008, Hillary was downing shots of whiskey with voters. Compared to Obama, she boasted, "I have a much broader base to build a winning coalition on." Now Clinton seeks to hold on to Obama's coalition. This August, she met with Black Lives Matter activists and tried to explain her husband's record. "I do think that there was a different set of concerns back in the '80s and the early '90s," Clinton said. "And now I believe that we have to look at the world as it is today, and try and figure out what will work now." The world today is not Jim Webb's world.