Earlier this year, Buzzfeed uncovered a 1979 television interview with Hillary 
Clinton—then Hillary Rodham—who had just become first lady of Arkansas. In the half-hour video, we see a young woman in oversize glasses, calm and smiling as the host grills her about whether she’s too liberal, too feminist, too career-oriented to fit into her new role. The host tells her that she probably cost her husband votes by keeping her last name. (She would later give in and change it.) “You’re not a native,” he says. “You’ve been educated in liberal Eastern universities. You’re less than 40. You don’t have any children…. You practice law.” (She assures him that she and Bill plan to have children and adds, “I’m not 40, but that hopefully will be cured by age.”) After nearly 20 minutes of this sort of thing, the host asks Clinton what she finds attractive about Arkansas—a place to which, her biographers have made clear, she moved with great reluctance to further her husband’s political career. Outsiders, he notes, complain that “We’re so unprogressive here. We’re just not as progressive as they are up North.” Appearing eager to finally ingratiate herself, she replies by pouring scorn on urban America: “You know, if it’s progress to default on your bond obligations so that your city’s going into bankruptcy, or if it’s progress to have such an incredible crime rate that people don’t venture outside their doors, or if it’s progress to live in a city whose air you can’t breathe, well, then I hope we are unprogressive, and I hope we never get to the point where that’s our definition of progress.”

This exchange exemplifies a dynamic we would observe over and over for more than two decades. For the first half of her political life, Hillary Clinton was consistently painted as so far left—so feminist—that it threatened her husband’s political viability. Whenever that viability was in doubt, she would overcorrect, trying to convince a skeptical mainstream press that she wasn’t nearly as liberal as she seemed. Eventually, the strategy of triangulation—using the left as a foil to prove her moderate bona fides—became nearly reflexive.

In recent years, however, America’s political context has been transformed. With the white South becoming solidly Republican—something that happened during Bill Clinton’s administration—the Democratic Party has become more reliant on the votes of women, people of color, and those who wear the “liberal” label proudly. This means that elections have become less about wooing swing voters than about turning out the base. Meanwhile, policies once supported by a smug centrist consensus—from Wall Street deregulation to military adventurism in the Middle East—have proved themselves failures, pushing the center of gravity in the Democratic Party to the left. Triangulation has become passé.

This means that, in a historical irony, Hillary Clinton now needs to convince progressives that she really is who she was once widely believed to be. She is running for president as a progressive feminist, something that would have been utterly quixotic when she entered public life. In a major address on the economy in July, Clinton emphasized the importance of women’s equality in a way that no mainstream candidate has done before, describing equal pay, accessible childcare, and fair scheduling as key to economic growth. She’s making paid leave a signature issue. “I am well aware that for far too long, these challenges have been dismissed by some as ‘women’s issues,’” she said. “Well, those days are over.”

It was thrilling language. Yet after spending so many decades trying to shed her reputation for liberalism, Clinton has amassed a record that many on the left find troubling, if not unforgivable. The wildfire growth of Bernie Sanders’s campaign suggests that a large part of the grassroots is dissatisfied with her. She will almost certainly be the Democratic nominee, but “the X factor is enthusiasm, which is going to be a real challenge,” says Rashad Robinson, executive director of ­ColorOfChange, the online civil-rights organization. “The question will be, for all of us: How will Hillary speak to the issues of the left?”

Whatever Clinton says, some will remain unconvinced. But in attempting to court progressive voters, Clinton isn’t adopting new positions; rather, she’s coming full circle. “I think her progressive résumé and her progressive roots are very, very strong,” says Congresswoman Jan Schakowsky, a progressive stalwart who backed Barack Obama eight years ago but is now an enthusiastic Clinton supporter. “Not only has she decided to go back to her roots, but the time is different. This is a progressive moment, I believe.” What remains to be seen is whether Clinton, after all the ideological maneuvering required to climb in US politics during a very different time, will be able to seize it.

* * *

Hillary Clinton was never a 
radical, but her formative political years were spent on the left. She did her undergraduate thesis on organizer Saul Alinsky, to whom she once wrote (in a letter unearthed by the right-wing Washington Free Beacon), “The more I’ve seen of places like Yale Law School and the people who haunt them, the more convinced I am that we have the serious business and joy of much work ahead—if the commitment to a free and open society is ever going to mean more than eloquence and frustration.” During law school, Clinton interned at Treuhaft, Walker & Burnstein, a radical law firm whose clients included the Black Panthers. In A Woman in Charge, Carl Bernstein’s 2007 biography of Clinton, he quotes Robert Treuhaft, the firm’s senior partner, as saying that Clinton was “in sympathy with all the left causes, and there was a sharp dividing line at the time. We still weren’t very far out of the McCarthy era.” After graduating, Clinton would eschew corporate law to work for Marian Wright Edelman’s Children’s Defense Fund, where she focused on the needs of migrant farmworkers.

Years later, when Clinton did enter corporate law, it was in order to provide her family with some economic stability amid the vicissitudes of her husband’s political career, which she saw as a vehicle for the sort of progressive change she longed for. Even then, she remained socially engaged: President Jimmy Carter appointed her to chair the Legal Services Corporation, the politically embattled organization providing free legal services to poor defendants. She was the first woman to hold the position.

* * *

When her husband
 became president, Hillary was solidly on the left of his administration’s ideological spectrum. During Bill Clinton’s first term, the White House was divided between those who wanted to prioritize healthcare reform, like Hillary, and deficit hawks like Robert Rubin, the former cochairman of Goldman Sachs, who cared most about balancing the budget. At one point, Bernstein describes her snapping at her husband: “You didn’t get elected to do Wall Street economics.”

When Clinton testified about healthcare before Congress in 1993, her disciplined passion mesmerized New York Times columnist Maureen Dowd, who would later become one of her most merciless critics. “Her bravura in back-to-back appearances today before two House committees carried a sense of wonder,” Dowd wrote. But the first lady’s crusading spirit was far from universally appreciated in the early days of the Clinton administration. In her biography Hillary’s Choice, Gail Sheehy quotes an exchange between Dick Morris, the mercenary pollster who had worked with the Clintons in Arkansas, and Clinton strategist James Carville, about Hillary’s plans for healthcare:

Mystified, he went to James Carville: “What’s with all this liberalism?”

“These fuckin’ liberals are all over the place!” exploded Carville. “They are like water damage. They seep in.”

After the Clintons’ attempt at healthcare reform went down in flames, the economic centrists in the White House got the upper hand. Hillary was widely blamed for the catastrophic 1994 midterms, in which Republicans, led by Newt Gingrich, won the House for the first time in 40 years. “My view is Hillary Clinton destroyed the Democratic Party,” Lawrence O’Donnell, the former aide to Senator Patrick Moynihan and current 
MSNBC host, told Bernstein. Personally shattered, Hillary threw herself into her husband’s strategy of triangulation, a word she uses approvingly in her own memoir, Living History. She even brought Morris into the White House, despite the fact that, during the midterms, he’d been working for Republicans. “Morris’s specialty,” 
Hillary wrote, “was identifying the swing voters who seesawed between the two parties.” The Clintons re
dedicated themselves to winning those voters over.

In his memoir, In an Uncertain World, Robert Rubin describes a conversation he had with Hillary and her ideological ally, Labor Secretary Robert Reich, after the midterm elections. According to Rubin, Reich believed that the Democratic base had been unmotivated and prescribed a more populist economic stance. Rubin, however, blanched at language like “corporate welfare,” arguing that it would “adversely affect business confidence” and be politically ineffective. Hillary, he wrote, agreed with him: “The polls and political intelligence we have say that the people we need to reach don’t respond well to that kind of populist approach,” she told Reich.

This was a typical pattern. Faced with a humiliating public rebuke for being too far to the left, she retreated to the safer center. “There’s this human quality of, when you are that buffeted and that challenged, you go back to the more conservative stuff,” says a former Clinton White House staffer. “What has been instrumental for her as a political person was also a survival mechanism for her as a human being. She had her identity publicly dismantled twice”—first during the 1992 campaign, and then during the Monica Lewinsky scandal. “She invests very heavily in American progressivism as a younger woman,” the staffer adds, “and it sort of hangs her out to dry.”

This doesn’t mean that Clinton abandoned progressivism entirely. According to Melanne Verveer, her 
former chief of staff, after healthcare reform failed, Hillary pleaded with her husband to expand the coverage for children, which he did through the State Children’s Health Insurance Program, passed in 1997. And Hillary remained particularly strong on women’s issues. In 1995, as the head of the American delegation to the United Nations’ Fourth World Conference on Women, held that year in Beijing, Clinton gave a speech that is widely seen as a watershed moment in the history of the global women’s-rights movement. “Twenty years later, you can see it really did begin this massive shift on how we look at gender and development,” says Heather Hurlburt, a former White House and State Department speechwriter who served as a consultant to Clinton when she was a US senator. “You have a dramatic change in the degree to which development is focused on women and women’s health and reproduction.”

Domestically, however, Clinton stopped sticking her neck out. Though uneasy about welfare reform, she didn’t oppose her husband signing it; according to Bernstein, “She accepted the decision as inevitable.” Nor did she try to distance herself from it later: In her Senate run in 2000, she made her support for the death penalty, welfare restrictions, and a balanced budget clear.

Yet once Clinton became a senator and had the opportunity to carve out her own political identity, she moved left once again. According to the vote-ranking system DW-Nominate, which is used by political scientists, Clinton is one of the more liberal senators when all her votes are tabulated, consistently to the left of Barack Obama, Joe Biden, and John Kerry. She voted against the Central American Free Trade Agreement, which her husband publicly supported, as well as Bush’s energy bill, which included $14.5 billion in tax breaks for the energy industry, and which Obama voted for. She attempted to establish a 9/11-style commission to investigate the federal response to Hurricane Katrina.

“I think she had a great record in the Senate,” says Larry Cohen, the recently retired president of the Communications Workers of America, who is volunteering for the Sanders campaign. According to Wade Rathke, founder of ACORN, the now-defunct community-organizing association, when Clinton was senator, “we couldn’t have asked for a better friend on any issue we had that involved ACORN in New York.” She advocated for the group’s housing programs and defended the Community Reinvestment Act, a 1977 law encouraging banks to make loans to people in low-income neighborhoods, when it was under fire by Republicans.

For most of the left, however, Clinton’s generally progressive Senate record was eclipsed by her vote authorizing the war in Iraq, her biggest overcorrection of all. Her observers are still debating whether the vote was one of misguided principle or political expedience. Most likely, it was both: Clinton is more hawkish than other Democrats, but also often responsive to political pressure. “I do believe there’s a good bit of ideology” behind the vote, says Rashid Khalidi, a professor of Middle Eastern Studies at Columbia University and the author, most recently, of Sowing Crisis: The Cold War and American Dominance in the Middle East. “On the other hand, she’s mainly a political operative; she will go with the wind, within the limits of her party.”

* * *

It’s easy to forget now, but
 when Hillary first ran for president, much of her platform was to Obama’s left, particularly on domestic economic issues. She called for a cabinet-level position “solely and fully devoted to ending poverty as we know it, that will focus the attention of our nation on this issue and never let it go.” Her healthcare plan was more far-reaching than the one Obama initially proposed. “We did a speech in Iowa in November of 2007 calling for regulation of derivatives,” says Neera Tanden, who worked on Hillary’s presidential campaign and now heads the Center for American Progress. “No one was talking about those issues.”

Yet the Iraq debacle haunted her—and though voting for it had been a disastrous mistake, it didn’t convince Hillary to stop triangulating in an effort to appear tough. Faced with Obama’s insurgent candidacy, Clinton resorted to Dick Morris–style tactics, painting her challenger as weak and radical and seeking to remake herself as the champion of the very sort of blue-collar white men who reviled her during her husband’s presidency. A particular low point was an interview she gave to USA Today, in which she said that “Senator Obama’s support among working, hardworking Americans, white Americans, is weakening again.”

This is the Hillary Clinton that many of today’s young activists remember. “We can’t pretend like that didn’t happen,” says ColorOfChange’s Rashad Robinson. Although she healed some of the wounds of that campaign when she became Obama’s secretary of state, he adds, “I don’t think it’s about the hard feelings—I think it’s about how much people sign up on the Love Train.”

Of course, during her tenure as head of the State Department, Clinton alienated the left in other ways. She was a major supporter of American intervention in Libya, and, if she’d had her way, the United States would have gotten more involved in the war in Syria. She also supported an escalation of the war in Afghanistan. “Hillary Clinton has many virtues,” says Juan Cole, a professor of Middle Eastern history at the University of Michigan. “I think she would stand up in important ways for labor; I think she’d be good on many domestic issues that progressives care about. But on foreign policy, she has been a hawk, and in that regard more hawkish than President Obama, whose hawkishness has disappointed a lot of progressives.”

Yet her hawkishness isn’t the whole story. As secretary of state, Clinton also brought the awareness of global women’s issues that she’d developed as first lady. At the United Nations, she led the push for Security Council Resolution 1888, which requires the UN to take steps to protect women and children from wartime sexual violence. She made sure that women’s concerns were represented in forums where they had traditionally been absent. Verveer, who served as the US ambassador for global women’s issues under Clinton, describes how she put women’s economic participation on the agenda at the 21-nation Asia Pacific Economic Cooperation forum. “There are aspects of her foreign-policy record that are profoundly progressive, and she’s done things that nobody else could do,” Hurlburt adds. “I think people miss that.”

Further, Clinton has defended President Obama’s nuclear deal with Iran, the most significant foreign-
policy issue of the day, despite the misgivings of some of her pro-Israel donors, particularly billionaire Haim Saban. “You have to give her credit,” says Khalidi. “Saban is one of the biggest funders of the campaign against the Iran deal, and she has taken a clear position on that.”

Indeed, most of the positions she’s taken in her current run should please progressives: Clinton has generally been more liberal than either she or Obama was in 2008. After her searing loss eight years ago, she appears to be fully cognizant of the way that American politics have changed since the 1990s. “The path to winning requires the Democratic presidential candidates to understand that the center of power in this country is no longer Third Way corporate ‘centrism,’” says Anna Galland, executive director of MoveOn.org Civic Action, one wing of the progressive organizing behemoth originally founded to oppose Bill Clinton’s impeachment. “The political center of gravity is now a populist center of gravity, and everyone needs to reckon with that. I think her campaign is savvy, and they will.”

* * *

Not everyone buys Clinton’s born-again
 progressivism. Bill McKibben, the founder of the activist environmental group 350
.org, is scathing about her record on the environment at the State Department. “She mishandled, at best, Keystone, which became the greatest environmental cause of recent decades in the United States,” he says. Clinton once said she was “inclined” to approve the pipeline, and as a presidential candidate has refused to take a position on it. As secretary of state, McKibben points out, she attempted to promote fracking overseas, and the 2009 Copenhagen Climate Conference “completely collapsed” on her watch and never reached binding targets on emissions reductions.

Now, McKibben continues, nearly all of the lobbyists bundling donations for Clinton have ties to the fossil-fuel industry. “If you’re going to deal with climate change, there’s no way to avoid squaring off with the fossil-fuel industry at some point,” he says. “It’s not one of these things where you can have everybody happy with you in the end, because we’re going to have to strand huge quantities of carbon, gas, and oil under the ground. The [Republicans] know this, which is why the Koch brothers are willing to invest immense amounts of money in the campaign.”

Still, in one of Clinton’s first public appearances in this campaign, she called for getting the money out of politics—“once and for all, even if it takes a constitutional amendment”—and she has pledged to appoint Supreme Court justices who will overturn Citizens United. Until that happens, Clinton defenders argue, it’s impossible to run a viable political campaign without cultivating powerful allies and raising a lot of money. Already, Clinton is far behind the GOP in that regard: The largest Super PAC backing Clinton, Priorities USA Action, has raised $15.7 million, while Jeb Bush’s Super PAC has drummed up $103 million; Scott Walker’s has raised $20 million. Even, the AP pointed out, Rick Perry, who didn’t qualify for the first Republican debate, has raised more in Super PAC funds than Clinton. “There is no hypocrisy in saying you can run a campaign according to the rules of the road while also saying that you want to change the system,” Lawrence Lessig, a Harvard professor who has launched a number of campaign-finance reform efforts, told the New York Times about Clinton’s fundraising.

Is Hillary Clinton uniquely or even particularly objectionable, then, for taking Wall Street and K Street money? After all, the single most common adjective that people attach to her is “pragmatic.” For example, Ellen Chesler, a longtime friend of both Clintons and director of the Women and Girls Rising Initiative at the Roosevelt Institute, describes her as “a genuine progressive, in terms of her thinking, who is also pragmatic, in terms of understanding the exigencies or requirements of moving forward in a two-party system or a federal government.”

* * *

In many ways, the progressive debate over Hillary Clinton is all about the limits of pragmatism: How much compromise can be excused by good intentions? When does realism become a complacent acceptance of the status quo? Cohen, for his part, refuses to call Clinton “pragmatic.” He prefers the word “practical,” arguing: “Pragmatic people believe in problem solving. Practical people often tell us why we can’t solve problems that we care deeply about.”

It is easy to overstate how widespread this sort of disillusionment with Clinton is. A recent survey by Public Policy Polling found that while 69 percent of Democrats view her favorably, 82 percent of those who describe themselves as “very liberal” do. But there is a fear, among many activists, that Clinton’s long history of cautious positioning has made it hard for the base to muster much enthusiasm. “This is going to be a stretch for a lot of people—to believe that this is where they should put their $20, that they should go down and volunteer and make phone calls,” Rathke observes. “There’s no heart beating; there’s no excitement.”

Saru Jayaraman, cofounder of the Restaurant Opportunities Centers United, a group seeking fair wages for restaurant workers, suggests that the lack of passion stems from a broader disenchantment with electoral politics, at least among the people she represents. “The real energy in my community isn’t actually around presidential elections at all,” she says. “It’s not around voting at all. Right now, it really feels like a moment of social upheaval. People are feeling like their form of democratic representation is taking to the street, taking action. Honestly, it’s not like my people are any more excited about Bernie Sanders.”

Jayaraman’s constituency is mostly female, and if they’re as disengaged as she says, it’s bad news for the Clinton campaign, which will need working-class women and women of color to turn out en masse. (A recent Wall Street Journal/NBC News poll showed that while 66 percent of black Americans have a positive view of Clinton, only 34 percent of white women do.) Yet Jayaraman is more sanguine about the Clinton campaign than Cohen is—and that’s largely because there’s one very big way in which a Clinton presidency would not be business as usual at all. It matters, Jayaraman says, that Clinton is a woman. It’s led her to pay attention to working-class issues that others miss, such as the plight of tipped workers, two-thirds of whom are women. “Every time the minimum wage has gone up in 43 states across the country, tipped workers have pretty much entirely been left out and stuck at $2 wages,” Jayaraman says. “Which means minimum-wage advocates themselves—people on the left—have left out half of the women in the minimum-wage population every time the minimum wage has gone up.”

At least in her rhetoric, Clinton isn’t leaving these women out. “The fact that she’s a woman, the fact that gender equality and income inequality are going to be two of the key issues of this campaign—[wages for tipped workers] really fits in the nexus of those two issues,” Jayaraman says.

Sixteen years ago, the late Barbara Olson, who served as chief investigative counsel to one of the House committees that investigated the Clintons in the 1990s, wrote Hell to Pay: The Unfolding Story of Hillary Rodham Clinton. In it, Olson warned: “Hillary is a woman animated by a lifelong ambition. That ambition is to make the world accept the ideas she embraced in the sanctuaries of liberation theology, radical feminism, and the hard left.” These were the words of a paranoid fanatic. Yet if, after all these years, Clinton were elected on a pro-childcare, pro-healthcare, pro-family-leave platform, it would represent a profound historical victory over the right-wing reaction that has dogged her for most of her life. Whether that’s enough of a victory to excite today’s ascendant left remains to be seen.