Imagine the following scenario: After eight long years, a Republican vacates his office. The Democrats, sensing the seat is theirs to win, put forth a number of strong, well-known candidates. Despondent Republicans lament a far-from-outstanding pool of candidates, including a would-be populist campaigning from his red pickup truck. One Democratic candidate emerges well-poised from a narrow primary win to become the first woman ever in the seat. The Republican Party, on the other hand, struggles to unify after a divisive primary. (A runner-up, endorsed by James Dobson, even considers an independent run).

Though the independent candidacy never materializes, the damage has been done. The Republican nominee relies heavily on personal finances as the Democrat soars ahead in fund-raising and, in a nearly evenly divided electorate, wins in November with 53 percent.

While this might sound like a plausible scenario for the 2008 presidential election--if Hillary Clinton makes it out of the primaries--it’s also the story of Tammy Baldwin’s 1998 congressional run in Wisconsin’s 2nd district. The similarities to Clinton’s potential race are admittedly scant. Though the 2nd district is a fair microcosm of the U.S. in its division between urban, suburban, and rural populations, it's also home to the liberal stronghold of Madison. But Baldwin, like both of the leading democratic nominees, was a historic first: America’s first-ever openly gay non-incumbent elected to Congress. There are lessons in her campaign that Clinton or Obama would be wise to heed.

The single most important issue Baldwin had in her favor was health care reform. Advocating for a single-payer system, Baldwin's message resonated in both Madison and the district's farmlands, where steep prescription-drug prices and the high risk of going without coverage made the high cost of health care foremost in voters' minds. At the same time, Baldwin was able to paint her Republican opponent, Jo Musser, an insurance commissioner in former governor Tommy Thompson's administration, as beholden to insurance companies. David Welch, a consultant to Musser, explained his candidate's disadvantage: "In general, if you have a Democrat and a Republican on health care, the Democrat is going to win. It just isn't a good Republican issue." It was true in 1998, and it will be true in 2008.

If it seems that Hillary is playing the heath care card now, hammering Obama for his less-ambitious universal-coverage plan, it will become even more central to Clinton's campaign in a general election. With more than 45 million uninsured Americans and a majority of the public in favor of some sort of reform, Republican candidates such as Rudolph Giuliani and Mitt Romney miss the point entirely when they sneer about socialized "HillaryCare." What was once her greatest political liability is becoming her greatest asset.

Clinton, like Baldwin before her, will also be able to turn perceived weaknesses into strengths if she can skillfully navigate the treacherous waters of negative advertising. As Free Congress Foundation chairman and CEO Paul Weyrich recently told The Hill, “You can’t go after a woman candidate the way you can go after a guy.” A candidate or a 527 seeking to portray Hillary in a negative light faces a delicate problem--how to attack the senator without seeming like a sexist bully. Clinton's hapless 2000 New York senate opponent, Representative Rick Lazio, over-aggressively approached Clinton's podium during a debate and was tarred as pushy and thuglike.

One GOP primary candidate seeking Baldwin's congressional seat sought to make an issue out of her sexual orientation--and it rebounded on him. During the primary, Ron Greer garnered media publicity, as well as endorsements from Christian right figures including James Dobson, for assailing Baldwin's "radical homosexual agenda." But the more significant effect of his statements were to galvanize gay, young, and liberal voters, for whom supporting Baldwin became a matter of fighting intolerance. Greer narrowly lost the primary, and the Republican nominee refused to touch the lesbian issue, it having been proved more trouble than it was worth. But by then, Baldwin had solidified her support and was sprinting towards a general election victory.

Though attacks on Clinton's womanhood are unlikely to be as straightforward as the slurs against Baldwin’s sexual preference, they're likely to have equally awkward undertones, especially when coming from men. Aggressive anti-Hillary attack ads, particularly the tired, sensationalist kind beloved by 527s, might only yield eye-rolls from moderates and an angrier, more motivated Democratic base.

The ability to run as a “first” was a huge help for Baldwin, and will be for Clinton as well. Baldwin used her double-first (first lesbian in Congress, first woman to represent Wisconsin in the House) status to enormous effect. She set a fund-raising record for her district, mostly from individual donors and PACs around the country excited by her historic run. The unprecedented fund-raising helped fund a grassroots campaign targeted at University of Wisconsin students. The campaign mobilized 1,700 student volunteers, and several Madison precincts with high concentrations of students went 90-10 for Baldwin. It was enough young voters to give Baldwin the competitive edge in the election.

These tactics, of course, are not so easy to replicate on the national scale. But with Clinton and Obama already pulling way ahead of the Republican presidential candidates in fund-raising efforts, the Democratic nominee is likely to be the best-funded candidate in the election, if not history. In addition to answering the likely Republican attack-ad barrage, this sort of money can underwrite campaigning methods that target traditionally underrepresented groups that are likely to become excited by the idea of helping a woman attain the presidency--young people and single women. As Baldwin told me when I interviewed her recently, "All of us have had, at one point in our lives, someone saying 'You can't do that, you're too young,' or 'You can't do that, you're too inexperienced,' or 'You can't do that, you're a woman.' Every American can relate to being told that 'you can't' for some reason or another. And I think if [Clinton] turns that around in a way that people relate to, then it becomes very empowering."

Of course, drawing any conclusions about the 2008 race from imperfect analogues like Tammy Baldwin's run may prove an exercise in wishful thinking. The campaign is too up-in-the-air, too unpredictable, too hostage to unforeseeable events. But it's worth appreciating that almost ten years ago, in a time and a district where conventional wisdom dictated that Baldwin should have had serious disadvantages--the woman issue, the lesbian issue, the problem of appearing too liberal for her constituents, to name a few--she turned the drawbacks to her own advantage. At the least, she helps dispel the myth that America's heartland voters won't support any Democrat who isn't a white male from the South.