The day that President Obama’s Affordable Care Act was signed, March 23, 2010, was also the day that the first challenges to the law were filed in federal court. Back then, the notion that health care reform could be overturned seemed remote. For one thing, it would require the Supreme Court to abandon decades of precedent. But nearly as big an obstacle, it seemed, was that the filer of the first suit to move forward was Kenneth T. Cuccinelli II, the attorney general of Virginia, a politician whose seven-year stint in the state legislature had earned him the nicknames “Crazy Cuccinelli” and “Kook-inelli.”

After becoming Virginia’s top lawyer in 2010, Cuccinelli altered the state seal to cover the exposed breast of the Roman goddess Virtus. He has also questioned whether Obama was born in the United States and suggested he might not register the youngest of his seven children for a Social Security number. (“A lot of people are considering that now, because it is being used to track you,” he told a supporter.) The Washington Post‘s editorial board has twice used the word “embarrass” to describe his effect on the commonwealth.

At the outset, Cuccinelli’s health care lawsuit seemed like exactly the sort of intemperate move one would expect from an upstart Tea Party politician who is more concerned with public displays of disaffection than results. And health care reform was far from Cuccinelli’s only gripe. He has also sued the Environmental Protection Agency over its power to regulate greenhouse gases and investigated a former climate-change researcher at the University of Virginia (UVA) for fraud. Last March, he notified state-run universities that their non-discrimination policies could not extend to gay students.

One year on, however, Cuccinelli’s health care challenge no longer seems so far-fetched. Last December, Judge Henry Hudson of Virginia’s Eastern District Court sided with Cuccinelli and ruled that the individual mandate was unconstitutional. Seven weeks later, in Florida, a similar lawsuit filed by more than two dozen attorneys general and governors also successfully challenged the law. Now, even the most determined naysayers have been forced to acknowledge the case’s viability. And Ken Cuccinelli, once easily derided as a mere troublemaker, has become something of a hero to conservative opponents of health care reform.

Long before Cuccinelli became a politician, it was clear that he was drawn to procedure and order, to clear delineations of right and wrong. He served on his college’s judiciary committee, and, at George Mason School of Law in Arlington, he ran for honor board chairman on a platform of firm retribution for violators. Fellow board members recall that he took his duties seriously and didn’t hesitate to schedule board meetings on weekends. In 1994, Cuccinelli oversaw the investigation of a student accused of interfering with the publication of a law journal. The inquiry dragged on for months; eventually the student refused to attend his own hearings and was expelled. While several colleagues on the board describe his management of the matter as fair, years later, something about the investigation troubles them. Maybe, they say, had another personality type been in charge, the case could have been resolved without ending the student’s law career. “It was all pretty black and white to [Cuccinelli],” one board member told me. “He was uncomfortable in the gray.” (Cuccinelli disputes this characterization. “I bent over so far backwards to accommodate him,” he says of the student.)

During the 1990s, Cuccinelli was a familiar sight on Northern Virginia’s GOP scene. But, when he first ran for the state Senate in 2002, his candidacy seemed so unlikely that a number of Democrats voted for him (Virginia has open primaries), thinking he’d be easy to defeat. When Cuccinelli went on to win the primary, the Republican vacating the seat, Warren Barry, backed his opponent. “I don’t want to make a habit of endorsing Democrats,” Barry said at the time, “but, in this case, the GOP picked someone whose thinking is so ancient, he would be an embarrassment to Northern Virginia.” Cuccinelli won by about 2,000 votes. It wouldn’t be the first time his detractors had underestimated him.