Before the 1992 Democratic primaries, Bill Clinton was hardly the favored candidate of organized labor. Unions in Arkansas faulted the governor for his state’s right-to-work law, low wages, unsafe working conditions and for backing management during strikes. “Bill Clinton is mainly the friend of big business,” the head of the Arkansas AFL-CIO said at the time. Many unions threw their early support behind Iowa Senator Tom Harkin. With a few major exceptions, Clinton earned labor’s endorsement by default after he won the party’s nomination.

Upon securing labor’s blessing, Clinton accused President George H.W. Bush of “sucker-punching” American workers and pledged a “common commitment” to the “forgotten middle class.” Those words soon rang hollow, as Clinton’s presidency confirmed labor’s worst suspicions. Clinton scrapped an economic stimulus package in favor of balancing the budget, appointed Wall Street bankers like Robert Rubin and Roger Altman to top positions in the Cabinet and ferociously twisted arms to pass the North American Free Trade Agreement (NAFTA) and subsequent trade pacts. Bill and Hillary Clinton rejected single-payer healthcare reform in favor of a complicated “managed care” plan meant to appease the private sector and only tepidly supported a strikers’ bill of rights, which failed to pass Congress. He named a good progressive, Robert Reich, as Labor Secretary but gave decision-making power affecting labor and the economy to Rubin and Altman and, later, political strategists Dick Morris and Mark Penn. By 1996 Reich had resigned, accusing Clinton of selling out.

Despite this poor record, Clinton defanged much of labor’s hostility through his personal charm, by cultivating friendships with top union bosses and signing union priorities like the Family and Medical Leave Act and repealing antilabor executive orders from the Reagan and Bush I era. By the end of his presidency, attitudes in labor circles were decidedly mixed. Depending on whom you asked, Clinton was either “a rose in the middle of the desert” or “a wolf in sheep’s clothing,” says Mark Smith, president of the Iowa AFL-CIO.

Today, operating in a very different political climate, Hillary Clinton has been careful to avoid animosity from labor in her own run for the presidency. As a senator from union-friendly New York, she has shown solidarity with battered upstate industrial cities and built close ties to the local labor movement, receiving an enthusiastic endorsement and “favorite sister” status from the New York AFL-CIO. She’s courted labor nationally as well, championing issues like the Employee Free Choice Act, dining with union bosses and recruiting veterans from labor, such as Mike Monroe of the Painters’ Union, to work on her staff. Her campaign treats labor officials with respect, returns their calls and solicits their opinions. She asked to hold a recent forum with the AFL-CIO in Detroit, a city ravaged by deindustrialization and trade policies like NAFTA. At her frequent appearances before labor crowds, she’s well versed and usually at ease, earning respectful and sometimes boisterous ovations.

“When I’m President,” she likes to say, “we’re going to stand up for labor and make sure workers can organize for good wages, safe working conditions and actually appoint people to the Department of Labor who are pro-labor!” Her campaign gives labor officials a three-page document, headlined “Fighting for the Rights of Working Families,” that summarizes the numerous letters she’s written on behalf of union drives in New York, campaign priorities such as universal healthcare and her record on issues like collective bargaining and overtime pay. The AFL-CIO gives her a 93 percent score on her Senate voting record, just below Barack Obama and John Edwards.

Clinton understands the role of unions in the Democratic Party as well as anyone. “Labor is a critically important constituency within the Democratic Party and plays an important role in the primary process,” says campaign spokesman Howard Wolfson. Though labor represents a dwindling share of the private-sector workforce, it remains a potent force politically. Union households make up nearly a quarter of the electorate, comparable to the religious right in size and manpower, and vote overwhelmingly Democratic. Historically, labor endorsements have helped play kingmaker with candidates like Walter Mondale in 1984 and Al Gore in 2000.

Yet labor’s record in 2004 was not good. Two major unions, AFSCME and SEIU, endorsed Howard Dean in November 2003 but later came to regret it after Dean’s early flameout. Many unions endorsed longtime ally Dick Gephardt (a current Hillary backer), whose candidacy also fizzled after a fourth-place finish in Iowa. John Kerry and John Edwards received one endorsement apiece. Since then, seven major unions, led by charismatic SEIU leader Andy Stern, have broken from the AFL-CIO and started the Change to Win (CTW) coalition. Labor managed to work together on a $100 million get-out-the-vote effort in the 2006 midterms, but it’s unlikely that will occur in the ’08 primaries. When the AFL-CIO convened in Chicago on August 7, no candidate received the two-thirds approval necessary to garner the federation’s endorsement for the primaries. By contrast, CTW chair Anna Burger says, “We would like to see if we can get to a common endorsement” separate from the AFL-CIO after CTW’s summit in September. But right now, though Edwards has the best chance with CTW, no consensus exists there either.

If Clinton doesn’t receive early endorsements, she needs to prevent others from getting them and then wrap up labor’s support in the general election, as her husband did. In the truly early days of the election cycle, the Clintons sensed that Edwards was fashioning himself as labor’s darling–huddling with striking nurses and janitors, rallying for a higher minimum wage and premising his campaign on eradicating poverty in part by empowering the labor movement. So Bill Clinton made a surprise appearance at the Change to Win convention in Las Vegas in March and pleaded with its leaders not to give an early endorsement to Edwards. The strategy has worked. Edwards remains a fan favorite, but there are worries he won’t be viable past Iowa, à la Tom Harkin in 1992 or Gephardt in ’04. And Obama, despite hailing from a strong union state, remains a new face to many in the rank and file and hasn’t been as aggressive as Hillary or Edwards in reaching out to labor. “It’s still wide open,” says AFSCME president Gerald McEntee, one of the Clintons’ closest allies in labor, “and a primary endorsement will be hard to make unless there’s a frontrunner leading the pack with real substance.” Hillary comes closest to fitting that bill.

Yet not too far beneath the surface, there are multiple tensions. One involves the people Hillary has assembled to run her campaign. The Nation reported in May that her chief strategist, Mark Penn, is head of a large PR firm, Burson-Marsteller, that aggressively helps corporations crush union organizing drives. In response, the heads of two influential unions, Bruce Raynor of UNITE HERE and James Hoffa of the Teamsters, wrote Senator Clinton a letter expressing their “distress.” SEIU’s Andy Stern and John Sweeney of the AFL-CIO placed follow-up calls. Penn subsequently “recused” himself from the company’s antilabor work, which he claimed never to have been part of, and Raynor met with Clinton in June to convey his concern. “Believe me, she’s well aware of the issue,” Raynor says. “It has the potential to hurt her with labor people.” Yet he’s not satisfied by the campaign’s response. “I don’t think Mark Penn should be involved in Democratic Party politics and be associated with antiunion stuff.” Further instances of Penn’s company blocking organizing drives are being investigated by various unions. In addition, Burson-Marsteller and another Clinton-aligned lobbying firm, the Glover Park Group, were recently hired by the government of Colombia, where more than 400 trade unionists have been killed over the past six years, to push for a US-Colombia trade deal that both US and Colombian labor bitterly oppose.

The people advising Hillary on economic policy also arouse labor’s ire. They include the Wall Street executives who crafted NAFTA and are now affiliated with the Hamilton Project, a probusiness Washington think tank. AFL-CIO secretary-treasurer Richard Trumka met with Senator Clinton on June 25 and pressed her on which advisers would be running the show if she was elected. Hillary told another labor leader that the Hamilton Project was “absolutely not” her economic team-in-waiting, as had been reported. “Labor has as much input as anyone,” says Mike Monroe, the campaign’s liaison to labor. Yet one of the founders of the Hamilton Project, former Deputy Treasury Secretary Roger Altman, a protégé of Robert Rubin who runs an investment bank in Manhattan, recently convened a series of economic policy groups on behalf of Clinton. Altman serves as a chief economic adviser, according to the campaign, along with Gephardt and Gene Sperling, another Hamilton honcho and Bill Clinton’s second-term national economic adviser. Despite what she says today, from labor’s point of view Hillary still surrounds herself with some objectionable friends, not to mention a free-trade-identified husband who would no doubt be closely involved in her Administration. For that reason, there’s still mistrust. “She’s been willing to listen,” says Leo Gerard, president of the United Steelworkers, “but I worry about the Rubin-Sperling-Altman and Hamiltons in her campaign.”

Antilabor policies promoted by Bill during the 1990s and Hillary’s sometimes contentious Senate votes on matters like the Iraq War are additional causes for concern. “NAFTA has huge baggage,” says CTW’s Burger. “The war in Iraq has huge baggage. The question is what she’s going to do about it now.” Trade alone was a major issue for labor during Bill Clinton’s presidency. “It colored our opinion of the Clinton Administration,” says an AFL-CIO official who requested anonymity. Hillary is fully aware of the declining popularity of unfettered free trade, which remains a dividing line in the party, and she has sought to distance herself from her husband’s legacy in this area. “NAFTA had some positives, but unfortunately it had a lot of downside,” she said at an AFSCME candidate forum in June. Before her AFL-CIO appearance in Detroit she came out against a proposed trade pact with South Korea. She told the Teamsters union in April that she opposed renewing fast-track trade authority for President Bush, which expired in June. In a concerted effort to appear more progressive, Clinton has ratcheted up her populist rhetoric, declaring that the country “has gone back to the era of robber barons.”

Another question, of course, is whether the former corporate lawyer and Wal-Mart board member means what she says. Clinton’s rhetoric about the outsourcing of jobs, for instance, has fluctuated depending on whether she’s in front of a labor audience or a pro-outsourcing crowd. “I don’t think she’s really a pro-labor candidate,” Peter Stamich, president of the local Steelworkers union in Akron, Ohio, told the Akron Beacon Journal after hearing her speak at a USW forum in Cleveland. At that event, Hillary denounced the Central America Free Trade Agreement but never once cited NAFTA. She skipped the Q&A.

John Edwards likes to say, “Wherever I am, I talk about the importance of organizing.” Hillary Clinton frequently trumpets the cause of labor these days. But as recently as last year, at a major speech before the Economic Club of Chicago, she didn’t refer to unions once. And the “American Dream Initiative” she chaired for the business-friendly Democratic Leadership Council last year made only a passing mention of labor. (Hillary took a leadership role in the DLC in 2005 but has not used the organization as a vessel for her presidential aspirations, as Bill did while chair in 1991.) Examples like these reinforce the skepticism, voiced by the AFL-CIO official, that there are “two Hillarys” and that the current one views labor as simply a box to check en route to the nomination.

Even so, a second President Clinton would probably have a tougher time abandoning labor. The open battle between unions and Clinton-allied, corporate-funded organizations like the DLC that raged in the 1980s and ’90s has largely subsided, with the latter now a weaker presence in the party. There is a consensus among a wide spectrum of Democrats on the need to enact bold policies like universal healthcare and to make it easier for workers to organize. It’s a credit to labor that in this electoral cycle, according to Chicago labor lawyer Tom Geoghegan, “every Democrat sounds like a labor Democrat.” In recent years–particularly after last fall’s midterms, when a wave of new populists were elected–the Democratic Party has moved closer to labor.

You’d think, given this newfound clout, that labor would be in a position to demand more from the candidates. Yet paradoxically–perhaps because of the betrayals witnessed during Bill’s presidency–labor is still reflexively hoping for small crumbs rather than transformational policies. Amid this backdrop, don’t expect labor to rock the boat. A Democratic victory in 2008 remains the top priority. “Electability is huge,” says AFL-CIO political director Karen Ackerman. “The mood in labor is: We’re getting beat up and desperately need a change.” In their view, if that entails putting another Clinton in the White House, so be it.