In the wake of Chief Justice John Roberts' stunning about-face in the Obamacare case, conservatives who follow judicial issues are asking themselves: Did we ever really know Roberts? Did we get him wrong?

Those nagging questions have led Republicans to think back to Roberts' rise through the Washington legal world from White House lawyer to the nation's highest court.

Roberts had solid Republican credentials. He served in both the Reagan White House counsel's office and, later, in the Justice Department under President George H.W. Bush.

In January 1992 Bush nominated Roberts to a place -- Clarence Thomas' old seat -- on the U.S. Circuit Court of Appeals for the District of Columbia. Many observers thought one conservative would be replacing another.

Certainly the Democrats who controlled the Senate saw it that way. Spotting Roberts as a future Republican star, they resolved to kill the nomination. And with the 1992 election approaching, they saw no reason to confirm a final-year Bush appointee when they could instead stall and see if a Democrat won the White House. Once Bill Clinton was elected, Roberts' court hopes were dead.

But Roberts was just 37 years old. He could wait -- which he did, through eight years of the Clinton administration.

In May 2001, President George W. Bush renominated Roberts for the D.C. Circuit Court. Again, he faced determined Democratic opposition, and his nomination went nowhere.

By the time Republicans won control of the Senate, in November 2002, Roberts had waited a decade for a seat on the appeals court. In the ugly atmosphere of the war over judges, Roberts became the poster boy for Republican anger at the Democratic blockade of Bush judicial nominees.

In us-versus-them politics, Roberts became "our guy" for Republicans. Determining his credentials as a philosophical conservative became less important than simply winning the confirmation fight for the GOP team.

In addition, Republican senators loved Roberts as a nominee because he was easy to defend. He didn't have any past scandals, and, since he had never been a judge, didn't have any quirky rulings to explain.

As a matter of fact, besides his glittering academic credentials and impressive resume, there wasn't a lot to say about Roberts. "He wasn't one of those who wrote op-eds and law review articles, and he didn't give speeches on issues," says one former Senate Republican aide involved in Roberts' appeals court confirmation. "He flew under the radar," says another former GOP aide who was also involved.

Still, with connections to Reagan, both Bushes and lots of Republicans, there seemed little reason to doubt Roberts' conservative bona fides. With Republicans in control of the Senate, he was confirmed to the circuit court in May 2003.

Yet two years later, when Bush nominated Roberts to the Supreme Court, little things -- or maybe not so little things -- popped up to make conservatives uneasy.

In the confirmation process, it emerged that Roberts, as a private attorney, had done pro bono work for Lambda Legal, the gay advocacy group that was fighting what became a key homosexual rights case, Romer v. Evans.

Roberts also troubled some conservatives by the positions he argued on behalf of plaintiffs in the giant antitrust case against Microsoft.

And while it was at first reported that Roberts had been a member of the Federalist Society -- standard procedure for conservative lawyers -- it turned out he had never, in fact, joined the group.

Roberts and his supporters -- among them Steve Schmidt, the operative chosen by the Bush White House to shepherd Roberts' nomination through the Senate before later going on to run John McCain's presidential campaign -- argued that Roberts was simply working as a lawyer, representing his clients as best he could, and his work didn't say anything about his judicial philosophy.

But that judicial philosophy wasn't really clear. "His ideological opinions he certainly kept to himself," says one of those former Senate aides. "He was a blank slate because he had represented so many different sides," says the other.

The public debate over Roberts echoed those private doubts. As Roberts sought confirmation, conservative commentators as varied as Charles Krauthammer and Ann Coulter called him a "tabula rasa."

In the end, Roberts just didn't give Democrats much of a target. He was confirmed, 78-22, in September 2005. Among those 22 Democrats who voted against Roberts were then-Sens. Barack Obama and Joe Biden.

Now Roberts has given Obama the biggest court victory of his presidency. But to uphold Obamacare, the chief justice had to execute logical twists and turns that left conservatives wondering what they really knew about him all along.

Byron York, The Examiner's chief political correspondent, can be contacted at byork@washingtonexaminer.com. His column appears on Tuesday and Friday, and his stories and blogposts appear on washingtonexaminer.com.