Fortune
On history’s stage: Chief Justice John Roberts Jr.
By Roger Parloff, January 3, 2011

As the youngest leader of the high court in two centuries, he has the energy, the intellect, and the votes to reshape our world.

In January 1993 principal deputy U.S. solicitor general John Roberts Jr. was arguing before the U.S. Supreme Court in a case brought by an inmate in a Nevada penitentiary. The prisoner, a nonsmoker who had been sharing a cell with a five-pack-a-day man, claimed that being subjected to so much secondhand smoke amounted to “cruel and unusual punishment” in violation of his Eighth Amendment constitutional rights. The United States, represented by Roberts, was siding with Nevada in arguing that the inmate’s plight did not rise to constitutional dimensions.

“What about asbestos?” Justice Byron White asked Roberts, according to the official tape of the argument. Could the warden of a prison with decaying asbestos pipes force an inmate to inhale those toxins too?

That would be different, Roberts said without hesitation. “When we go to a restaurant, they don’t ask, ‘Do you want the asbestos section or the non-asbestos section?’ They do ask, ‘Do you want smoking or nonsmoking?'”

The response, which broke up the room, illustrates a few of the traits that made Roberts “the best Supreme Court advocate of his generation,” in the estimation of Tom Goldstein, a leading practitioner of the craft today, and the “gold standard” that such lawyers aspire to, according to Ted Olson of Gibson Dunn & Crutcher, another member of that guild. Tapes of Roberts’ arguments before the Court — he delivered 39 of them — bear out what numerous contemporaries recount: He seemed to anticipate every question, and responded instantly in complete, grammatical sentences salted with down-to-earth analogies and an occasionally wicked wit.

Since 2003, Roberts has been working the other side of the lectern, first as a federal appeals court judge and then, since September 2005, as the 17th Chief Justice of the United States. Just 50 when he assumed that post, Roberts became the youngest Chief Justice since John Marshall was appointed to the job by President John Adams in 1801. With good health, Roberts could surpass Marshall’s record as the longest-serving Chief Justice (34 years) in March 2040. Along the way he’ll have a fair shot at surpassing in stature every Chief Justice except Marshall (who wrote Marbury v. Madison, the bedrock 1803 opinion establishing that the Supreme Court is empowered to strike down acts of Congress that in its view conflict with the Constitution).

“He’s going to go down as an absolutely historic figure,” predicts Goldstein, who co-heads the litigation department at Akin Gump Strauss Hauer & Feld and is also the publisher of SCOTUSblog.com, an authoritative court-watching site. “John Roberts is the leader of a Court with five solidly conservative votes for the first time in its modern history,” he continues. “He’s an incredibly telegenic, energetic, thoughtful person, a great speaker — but in addition he has the fifth vote. So while … the [Chief Justice William] Rehnquist Court was more conservative than the [Chief Justice Warren] Burger Court, which was more conservative than the [Chief Justice Earl] Warren Court, it’s the Roberts Court in which the rubber will hit the road.”

The question is not where the Court is headed — it is headed to the right — but rather how quickly and how far. The exclusionary rule, requiring courts to exclude illegally seized evidence in criminal cases, hangs by a thread. Abortion rights could erode further. More shoes are apt to drop in the realm of race and gender discrimination: Not only is affirmative action on the ropes, but some Justices believe that key provisions of the civil rights laws — those allowing violations to be proved by statistical disparities — are unconstitutional.

And while most experts predict that President Barack Obama’s health-care reform law will be upheld by the Court, their perspectives are not shared by some Republican judges, one of whom, in Virginia, invalidated a key provision of that law last month. If the high court were to strike down Obama-care, progressives would receive the news as marking the arrival of a full-fledged constitutional crisis, the likes of which we have not seen since the mid-1930s.

The Roberts Court is also widely seen as pro-business — “Supreme Court Inc.,” the New York Times Magazine called it in 2008. Since 2006, according to the liberal Constitutional Accountability Center, the Roberts Court has ruled for business interests in 68% of the cases in which the U.S. Chamber of Commerce submitted friend-of-the-court briefs. During a comparable span (1981–86) drawn from the Burger Court years, the Chamber’s win ratio was just 43%. Close to 80% of the Chamber’s wins before the Roberts Court have been by votes of 7-2 or better.

The Court’s “corporatist” rap was further cemented last January, at least in popular perception, when it decided Citizens United v. Federal Elections Commission, finding that the First Amendment’s free-speech clause guaranteed corporations (and unions) the same unfettered right to make independent election expenditures as is enjoyed by flesh-and-blood citizens. The holding struck down federal laws going back to the 1940s, and state laws back to the 1890s.

Confronted with blockbuster rulings like that one, some liberals have cried foul, protesting that Roberts snookered them at his confirmation hearings, and that the new majority he commands is acting lawlessly.

Both criticisms ring hollow. The numbers have simply caught up with liberals (and maybe with moderates too). For 42 years left-of-center Americans have been flirting with disaster vis-à-vis the Court, and now they’ve finally married it. Since 1968, Republicans have held the White House for twice as many years as Democrats (28, compared with 14), and they’ve made three times as many appointments to the Supreme Court (12 to 4). With President George W. Bush’s 2006 replacement of the moderate Justice Sandra Day O’Connor by Justice Samuel Alito Jr., a dependable conservative vote, the ideological center of the Court shifted from O’Connor to Justice Anthony Kennedy. Kennedy is “on a number of critical hot-button questions, like abortion and race and religion, materially more conservative than O’Connor was,” says Goldstein.

“Because there is a constant change in membership on the Court influenced by the political process,” says one Supreme Court advocate, “it’s hard to sustain a view of the law when there’s a sustained popular majority that rejects it.” Eventually the disconnect results in modifications in constitutional doctrine. (Most of the eight Supreme Court advocates interviewed for this story requested anonymity because their firms constantly have cases before the Court.)

Future presidential elections will continue to reshape the Court’s composition. In the meantime, we should get to know Chief Justice Roberts. He’s going to play a pivotal role in our lives for much longer than President Obama or John Boehner or Sarah Palin. He’s not the man liberals briefly kidded themselves into thinking he was or might become. He is a long-standing, committed conservative. He is President George W. Bush’s most lasting and most competent legacy.

He’s also a remarkable man, and with such people there cannot but be some silver linings for everyone. (Roberts declined to be interviewed for this article.)

Anatomy of a skilled Supreme Court advocate

The advocate’s podium at the Supreme Court, around which so much of Roberts’ career has revolved, is closer to the bench than at other appeals courts. The nine-Justice bench is divided into three segments, with each flank jutting toward the advocate as if to surround him.

The advocate typically gets only a few sentences into his presentation before he is interrupted by a volley of questions from all angles, literally and figuratively. Because of the courtroom geometry, the advocate can see only about three Justices at a time, so he’ll often be literally blind-sided. He’ll identify the Justice by voice and then pivot to address him or her.

Though practices have varied over time, 45 questions per half-hour argument is about average, and 80 is not unheard-of. The clock is ticking, and a white podium light goes on when the advocate has five minutes left, a red one when his time is up. The questions are sharp, probing, confrontational, and sometimes sardonic. The advocate must respond directly, while striving to keep a cordial demeanor.

While performing those mental and emotional feats, the advocate is forever calculating. “You have to think not just how the answer to this question is going to work,” says Olson, “but what that’s going to mean for other yet unasked questions. And you don’t want to please one Justice and alienate two others at the same time.”

When Roberts was preparing an oral argument, he would write down — usually longhand, using a pen and a legal pad — hundreds of questions that he might conceivably be asked. He’d ponder and refine the answers in his mind. Then he’d write the questions on flash cards, shuffle them, and test himself, so he’d be prepared to answer any question in any order.

In a talk to oral advocates in 2004, Roberts urged them to approach their craft with the mindset of a medieval stonemason. “Those masons — the ones who built the great cathedrals — would spend months meticulously carving the gargoyles high up in the cathedral,” he told them, “gargoyles that when the cathedral was completed could not even be seen from the ground below. The advocate … must meticulously prepare, analyze, and rehearse answers to hundreds of questions, questions that in all likelihood will actually never be asked by the Court. The medieval stonemasons did what they did because, it was said, they were carving for the eye of God … The advocate who stands before the Supreme Court … also needs to infuse his craft with a higher purpose. He must appreciate that what happens here, in mundane case after mundane case, is extraordinary — the vindication of the rule of law — and that he as the advocate plays a critical role in the process.”

From Indiana to Harvard to Washington

Roberts’ father and mother, Jack Roberts and Rosemary Podrasky, both grew up in Johnstown, Pa., near Pittsburgh. Jack studied electrical engineering at the University of Pittsburgh, as did two of Rosemary’s brothers. (Rosemary didn’t go to college.)

Upon graduation in 1951, Jack landed a job at Bethlehem Steel, where he rose quickly. Steel was king, and Bethlehem was one of the nation’s mightiest and most remunerative corporations. Jack’s career took him to mills across the Northeast and Midwest, and he eventually managed three of the company’s largest plants.

Jack and Rosemary had four children, who were raised as a tight-knit Catholic family. The second was John Glover Roberts Jr., the only boy. John was born in Buffalo but grew up in Long Beach, Ind., a small community on the shores of Lake Michigan. For high school John attended a Catholic boarding school called La Lumiere, near LaPorte, Ind., where about 100 boys roamed an idyllic 155-acre campus. La Lumiere sought to produce well-rounded young men, and in Roberts it hit the jackpot: He was a standout in football, wrestling, drama, journalism, student government, and academics.

Roberts entered Harvard in 1973, graduated summa cum laude in history in three years, and won the college’s most prestigious writing award, the Bowdoin prize for “best dissertation in the English language.” He continued on to Harvard Law, where he became managing editor of the law review, its No. 2 officer.

After graduation, Roberts clerked for two of the most august judges of their eras. The first was Judge Henry Friendly, a federal appeals judge in Manhattan. Friendly was the archetypal judge’s judge, a meticulous craftsman, a fine writer, and hard to pigeonhole politically. One of Friendly’s lines that Roberts has quoted in his own opinions is a wry appeal to common sense: “Judges are not required to exhibit a naiveté from which ordinary citizens are free.”

In July 1980, Roberts moved on to a judge of a very different stripe, Associate Justice William Rehnquist. Rehnquist, who would be elevated to Chief Justice in 1986, was then unmistakably the most conservative voice on the Court, often writing in dissent. “He stood alone in his view of the law to such an extent,” Roberts later said, “that his law clerks bought him a Lone Ranger doll.”

About halfway through that clerkship, Ronald Reagan was elected President. Roberts accompanied Rehnquist to Reagan’s first inaugural in January 1981.

“I was trying to decide what to do next,” said Roberts in a speech at the Reagan Library in 2006. “Then he spoke these words and, like so many of the President’s words, I felt he was speaking directly to me. He said, ‘I do not believe in a fate that will befall us no matter what we do; I do believe in a fate that will fall on us if we do nothing.’ And that is what Ronald Reagan was and is and remains today to me: a call to action.”

Sometime thereafter Justice Rehnquist telephoned Reagan’s first attorney general, William French Smith, to recommend Roberts, according to Ken Starr, who was then Smith’s chief of staff. (Starr later became the independent counsel whose investigation of the Monica Lewinsky affair led to President Bill Clinton’s impeachment trial. He is now president of Baylor University.) In August 1981, Smith hired Roberts, 26, as one of his special assistants, effectively commissioning him as a young officer in the Reagan revolution.

“All of us who followed the Reagan wave ashore came to Washington with what can indeed be called revolutionary zeal,” Smith wrote in his memoir. (He died in 1990.) In the legal realm, Reaganites hoped to roll back what they saw as the excesses of the Warren and Burger Courts, including their recognition of abortion rights, the exclusion of illegally seized evidence from criminal trials, the banning of prayer in public schools, “forced busing” to achieve racial balance, and “quotas,” as all forms of affirmative action were rhetorically referred to.

At that time Roberts “looked at the world through an analytical lens more than an ideological lens,” as Starr remembers it. “He was first and foremost a lawyer.”

He was also well-liked, Starr says, because, despite his brilliance, he presented himself as a down-to-earth, humble Midwesterner — a fan of Notre Dame football and Indiana Hoosier basketball. “He may’ve been double Harvard with honors,” says Starr, “but he came across as a son of the heartland.”

Smith promptly assigned Roberts backstage roles in two events of historic moment. His first was to help prep Sandra Day O’Connor — the nation’s first woman Supreme Court nominee — for her confirmation hearings. His second was even weightier and, later, controversial. Because liberals still had a majority of votes on the Supreme Court, when it came to issues like abortion, school prayer, and busing, several powerful Republican senators were then urging Reagan to support legislation that would have stripped the Supreme Court of jurisdiction to hear such cases. Whether Congress had the power to emasculate the Court in this fashion was one of the ancient conundrums of American constitutional law, long debated by scholars. (The Constitution vests the Supreme Court with “appellate jurisdiction … with such exceptions … as the Congress shall make.”)

Ted Olson, who then headed Smith’s Office of Legal Counsel, advised Smith that such legislation would violate the Constitution. But Smith wanted the other side of the argument briefed, and he assigned Roberts that task. Roberts’ resulting memorandum awed Starr and Olson with its scholarship, craftsmanship, and the persuasiveness of its writing. Fortunately for the nation, it did not convince Smith, who adhered to Olson’s recommendation. The memo — in which Roberts was simply carrying out an assignment, to be sure — would later become an issue at Roberts’ confirmation hearings.

In fall 1982, Starr remembers getting a call from White House counsel Fred Fielding, a famously keen judge of talent. Fielding greeted him, “Hi, Ken. Raiding party!” He wanted Roberts, who became an associate White House counsel that November.

“I vividly remember my first day on the White House staff,” Roberts later recalled in his Reagan Library speech. “My office, of course, was in the Old Executive Office Building. I didn’t rate one in the West Wing; but don’t try to tell me or any of the rest of us working there that we weren’t working in the White House.

“Then the phone rang,” his story continued. “Could I hold for the President? Well, yes, I could. This was an example of the President’s famous charm, with all he had to do, calling a new staffer on his first day to wish him well. I did, I think, what most people do when they get a call from the President at their desk: I stood up. A few minutes went by, but of course that’s understandable, he’s the President, he’s probably finishing up a call with Brezhnev or something. A few more minutes went by … I sat down. I figured that I’d stand up when the President came on the line … A few more minutes went by. Then I heard the muffled laughter outside my door … I put the phone down and went to the little anteroom. In there, of course, were my new colleagues in the White House Counsel’s office, who had placed the phony call from the President. They had a betting pool how long I would stay on hold … Whoever had the 15- to 20-minute slot won that money.”

Self-deprecating anecdotes aside, Roberts, then 27, was frequently in the actual White House, and sometimes flew on Air Force One with the President. Decades later some liberals, charmed by Roberts’ performance at his confirmation hearings, seemed willing to forgive Roberts his Reagan years, as if they had been a youthful indiscretion. But Roberts appears to look back at them with a soft-focus, Peggy Noonan-like reverence, the way Wordsworth looked back upon the French Revolution: “Bliss was it in that dawn to be alive, But to be young was very heaven!”

During a question-and-answer period after his Reagan Library lecture in 2006, Roberts was asked what he had learned from Reagan. “He taught us the importance of ideas,” Roberts responded. “People talk of him as the Great Communicator … but that detracts from what he was. He was a great communicator because he communicated great ideas with the sincerity of a deep-felt and abiding belief in those ideas … It is vitally important … to examine the ideas that underlie your conduct and actions, and make sure you’re content with those, and then stick with those. That’s the overriding lesson of Ronald Reagan for me.”

Roberts left government in April 1986 to become a Supreme Court advocate. He was recruited by the firm now known as Hogan Lovells, whose appellate unit was then headed by E. Barrett Prettyman Jr.

“This is not your ordinary man,” says Prettyman of Roberts. “Not your ordinary lawyer.” Prettyman, 85, has met his share of talented men and lawyers. The U.S. Courthouse in Washington is named after Prettyman’s father, who was a federal appeals court judge, and Prettyman himself was a special assistant to Attorney General Robert F. Kennedy and President John F. Kennedy during the 1960s.

First, Prettyman says, Roberts is “just smarter than hell.” Even against the elevated baseline of appellate advocates, Roberts was “just smarter than the next guy.”

Prettyman worked with Roberts for 13 years, and probably had more lunches with him than anyone outside Roberts’ family. Most of those took place at a table in the firm’s cafeteria, where partners would gather daily to discuss current affairs. The table was then known as the Fulbright table, after Sen. J. William Fulbright, who joined Hogan when he left the Senate in 1975. Today, of course, it’s the Fulbright-Roberts table.

When Roberts was confirmed as Chief Justice, his son, Jack, then 4 years old, said, “Daddy, do you get a sword?”
Though all the stars must be aligned for anyone to become Chief Justice, Prettyman says he was not surprised to see Roberts become a federal appeals judge. “He’s the only person I’ve ever seen who was actually headed toward that position, and acted accordingly, before he ever got into serious consideration,” he says. “He always dressed while at lunch in coat and tie,” even when “business casual” became the norm.

“He has a private side to him, which he watches carefully,” Prettyman adds. “He’s a fellow who has carefully seemed totally outward in everything but who’s — I don’t want to say ‘guarded’ — he doesn’t just say anything that happens to occur to him.”

A lifelong liberal Democrat, Prettyman long ago made his peace with the enigma of how this man he liked and admired so much could hold political views so at odds with his own. “When we worked together on cases,” he recalls, “we hardly ever disagreed about what approach to take, the questions presented, what we’d put in or take out. But I don’t agree with hardly anything he’s written on the court.”

Which was no surprise after all those lunches. “You could foresee this exactly,” he says. “This was a man who had these thoughts, tendencies, and beliefs for many, many years.”

The road to the U.S. Supreme Court

In October 1989, Roberts interrupted his career at Hogan to join the administration of President George H.W. Bush. Bush had appointed Ken Starr as his solicitor general, and Starr had invited Roberts to become his principal deputy.

The solicitor general usually decides what positions the U.S. will take in cases before the Supreme Court. Roberts became “my very closest, most trusted adviser,” Starr says, and he was “involved personally in substantially every single case of moment.”

During his three years with Starr, Roberts argued 19 cases before the Court. (Roberts has jokingly referred to lawyers like himself, with multiple Supreme Court arguments under their belt, as “recidivists.”) While Roberts can’t be assumed to have favored all the positions he argued there — he was representing a client — it is also true that as principal deputy solicitor general he usually had a say in what position the client chose to take. During the first Bush administration, the solicitor general’s office consistently defended laws restricting abortion, opposed racial quotas and set-asides, helped states try to impose the death penalty, and supported attempts to narrow the scope of the exclusionary rule.

The case of the Nevada prisoner complaining about secondhand smoke, with which this article begins, was a reasonably typical case. There Roberts was helping wardens efficiently administer their prisons. He was also, from a liberal perspective, blindly trusting in the goodwill of wardens not to subject prisoners to medical risks. The inmate in that case had been assigned to share a six-by-eight-foot cell with a man who, in effect, smoked one cigarette every 10 minutes during every waking hour, the prisoner’s lawyer argued. Notwithstanding Roberts’ masterful argument, the Court ruled 7-2 for the prisoner.

When President Bill Clinton took office in January 1993, Roberts returned to private practice at Hogan. Soon thereafter he reconnected with Jane Sullivan, whom he had first met in 1991 at a summer share at the beach.

The daughter of Irish Catholic immigrants, Sullivan had grown up in modest circumstances in the Bronx. She graduated magna cum laude in math from the College of the Holy Cross, got a master’s in applied math from Brown, a law degree from Georgetown, clerked for a federal appeals judge, and in 1987 joined the firm now known as Pillsbury Winthrop Shaw Pittman. (Today she is a managing director of Major Lindsey & Africa, a legal recruitment firm.)

In July 1996, Roberts and Sullivan, both 41, were married at Washington’s oldest Catholic church, St. Patrick’s. Four years later, in 2000, John and Jane Roberts adopted two blond infants, Josie and Jack. The Robertses today worship at a parish in Bethesda, Md., headed by the priest who married them, Monsignor Peter Vaghi, the former pastor at St. Patrick’s. Vaghi, who was a lawyer before he turned to the cloth, happens to be a longtime friend and Holy Cross schoolmate of Justice Clarence Thomas. (There are currently six Catholics, three Jews, and no Protestants on the Supreme Court.)

The role religion plays in John Roberts’ life appears to be a private one. Prettyman and Olson each say they don’t remember knowing that he was Catholic until he was nominated to the judiciary.

George W. Bush became President in January 2001 and that May nominated Roberts to the federal appeals court in Washington. It was Roberts’ second nomination to that court, since Bush’s father had tried to put him there in 1992, when Roberts was just 37, but that time his name never got out of committee. In May 2003, after two more years in a political holding pattern, Roberts was unanimously confirmed.

The first opinion he penned, before his first clerk had even reported for work, was possibly his most controversial on that court. It was a very brief dissent to a decision by the full Court not to rehear a case in which a three-judge panel had upheld the application of the Endangered Species Act to the protection of a creature called the arroyo toad. The potential sticking point, advanced by a real estate developer, was that the law had been passed on the basis of Congress’s constitutional power to regulate interstate commerce, yet it was being applied here, as Roberts memorably put it, to “a hapless toad that, for reasons of its own, lives its entire life in California.” The question then arose: Was the survival of a commercially useless toad whose habitat was entirely intrastate a matter that Congress could properly address under its power to regulate interstate commerce?

Though Roberts did not answer that question — he urged the court to decide the case on a different basis — his opinion hinted at a willingness to reexamine one of the pillars of modern American constitutional law. Since at least 1937 the Supreme Court has generally interpreted Congress’s power to regulate interstate commerce very broadly. But in controversial rulings in 1995 and 2000, the Rehnquist Court had, for the first time since the New Deal, read the clause narrowly again. Liberals had been horrified — and libertarian conservatives elated — because these opinions suggested that once-settled precedents might now be in play again. That was a development that, taken to its limits, could lead to the dismantling of the modern bureaucratic federal government.

With this profoundly unsettling, drily amusing, enigmatic little dissent, Roberts announced his arrival on the federal bench.

Confirmation process: Wolf in moderate’s clothing?

In July 2005, after Justice Sandra Day O’Connor announced her intention to retire, President Bush nominated Roberts to succeed her. When Chief Justice Rehnquist died on Sept. 3, Bush withdrew that nomination, and renominated Roberts to succeed Rehnquist as Chief Justice.

Although people now argue that Roberts’ was a “stealth” nomination, that is true only in the sense that every Supreme Court nominee since Judge Robert Bork, who was rejected by the Senate in 1987, has been a stealth candidate. After a long, combative career in academe and government, Bork had a paper trail that was extensive and provocative, and no President has nominated anyone like him since.

That said, Roberts was hardly a black box. He had worked for eight years as a political appointee in two Republican administrations; he hadn’t been conscripted. In response to Senate Judiciary Committee requests, the Reagan Archives released 60,000 pages of memos Roberts had written during his Reagan years. They looked to be the work of an enthusiastic, cocky twentysomething cadre in the conservative movement.

Again, there was that distinctive, sharp-edged humor. In one memo, responding to a congressman’s request for a conference to discuss power sharing with the White House, he had written, “There already has, of course, been a ‘Conference on Power Sharing.’ It took place in Philadelphia’s Constitution Hall in 1787, and someone should tell Mr. Levitas about it and the ‘report’ it issued.”

There were some mildly offensive jokes too. In one memo referring to congresswomen concerned about the gender pay gap, he wrote, “Their slogan may as well be, ‘From each according to his ability, to each according to her gender.'”

Nevertheless, deploying the same brilliance and painstaking preparation that had been his stock-in-trade as a Supreme Court advocate, Roberts turned a potential ordeal into a tour de force. “I was just astounded how good he was,” says Olson. He remembers driving to dinner one evening and listening to the proceedings on the car radio when Roberts was asked to address the gnarly relationship between the First Amendment’s “establishment” and “free exercise” of religion clauses. “I pulled off the road so I wouldn’t get to the restaurant too soon,” Olson recalls, “because I thought that was the most lucid explanation of a terribly difficult area of the law that I’d ever heard. He was like that over and over.”

Roberts exuded erudition while maintaining an easy, down-to-earth manner. Explaining why he believed that the judicial role was a limited one, he said, “The Framers were not the sort of people, having fought a revolution to get the right of self-government, to sit down and say, ‘Let’s take all the difficult issues before us and let’s have the judges decide them.’ That would have been the farthest thing from their mind.”

And he was funny. One senator asked, “What would you like history to say about you when it is all said and done?”

“I’d like them to start by saying he was confirmed,” he replied.

Over time, his bravura performance charmed many Democrats too. Sen. Ted Kennedy’s questioning began on a forbidding note: “I am deeply troubled by the narrow and cramped and perhaps even mean-spirited view of the law that appears in some of your writings.” Then Kennedy read him a lofty but confusing quotation from former Justice Benjamin Cardozo and asked, “What do you think Justice Cardozo meant by that passage? And do you agree with it?”

“I know I agree with it,” Roberts said promptly. “Now let me figure out what he meant by it.”

It is likely that Roberts’ humor and charm helped liberals fool themselves into thinking he must be a moderate. “In Washington,” says one Supreme Court advocate, “people expect very conservative people to be ogres. John Roberts isn’t an ogre. But it just may happen that he’s a very nice guy and he’s very conservative.”

In late September 2005, Roberts was confirmed, 78-22.

Roberts later recounted the reaction of his son, Jack, then 4, to the news that his father had become the Chief Justice: “He said, ‘Daddy, do you get a sword?’ And I said, ‘No!’ I wondered why he asked that. If you go to the Supreme Court, the statue of Lady Justice out there, of course, is holding a giant sword, and he had seen that and had assumed if you’re the Chief Justice, you got a sword. So he is not very impressed.”

The rightward shift at the Court

After five-and-a-half years on the high court, Roberts’ honeymoon is over.

“No More Mr. Nice Guy,” ran the headline for a 2009 New Yorker profile, which was subtitled “The Supreme Court’s Stealth Hard-Liner.” “Roberts’ Record … Defies ’05 Pledges of Centrism,” the Chicago Tribune wrote in 2008. “Judicial minimalism is gone,” the New York Times reported at the close of last term.

And it’s not just the press.

“It is not often in the law that so few have so quickly changed so much,” Justice Stephen G. Breyer said ruefully while dissenting orally from the bench in June 2007.

“Gosh,” said former Justice O’Connor last January, “I step away for a couple of years, and there’s no telling what’s going to happen.”

Though the Roberts Court has now handed down more than 350 rulings, it is a handful of blockbusters that account for most of the criticism — foremost among them the Citizens United campaign-finance case last term (which triggered O’Connor’s remark) and a pair of race-related cases in 2007, decided under the caption Parents Involved in Community Schools v. Seattle School District No. 1, which struck down voluntary race-conscious attempts to achieve racial balance in schools (prompting Justice Breyer’s lament). Roberts had written the lead opinion in the school cases, capping it off with a characteristic rhetorical flourish: “The way to stop discrimination on the basis of race is to stop discriminating on the basis of race.” For conservatives, Roberts’ kicker was cathartic in its concise, analytical purity; for liberals, it was galling in its historical unreality.

The momentous ruling in Citizens United was all the more controversial because of the very unusual procedural posture of the case: The parties had not originally raised the constitutional questions that the Court ultimately decided, and as a consequence the lower court never heard testimony on those issues. In the sharpest imaginable rebuke to Roberts — the stonemason toiling in the cathedral — Justice John Paul Stevens had written, “The path [the Court] has taken to reach its outcome will, I fear, do damage to this institution.”

But none of the legal theories upon which either case was decided were invented by Roberts. (Citizens United was written by Justice Kennedy.) The theories were all respectable, long-standing, widely held — if minority — views and, in the case of Citizens United, views held not just by conservatives. The provision of the McCain-Feingold law that the Court struck down in Citizens United had criminalized airing electioneering ads on TV right before elections unless the ad was financed in certain ways. Many First Amendment experts, including press-freedoms icon Floyd Abrams, had always seen that provision as a blatant, indefensible ban on “core political speech” — the crown jewels that everyone agrees the First Amendment is supposed to protect. At oral argument Abrams had begged the Court to rule broadly lest this law continue to “chill,” or deter, the expression of protected speech.

“It’s been a tortured doctrine for a long time,” says one Supreme Court lawyer who was not involved in the case. “I think the Justices probably sometimes think, ‘We’re the Supreme Court. We need to clean this up. Let’s just do it now.'”

Roberts wrote separately in Citizens United to defend the procedural handling of the case. “We have had two rounds of briefing in this case, two oral arguments, and 54 amicus briefs to help us carry out our obligation,” he concluded. “This careful consideration convinces me that Congress violates the First Amendment when it decrees that some speakers may not engage in political speech at election time, when it matters most.”

Most Supreme Court advocates and professors interviewed for this article say that they continue to believe — Citizens United and Parents Involved notwithstanding — that Roberts’ respect for precedent and his concern for the Court as an institution are real, and do act as significant restraints on his jurisprudence.

Roberts is obviously far more deferential to precedent, Goldstein pointed out, than, say, Justice Thomas, who, according to SCOTUSblog’s tallies, urged major reconsiderations of existing law eight times last term. Roberts has repeatedly gone to great lengths to avoid striking down legislation and overruling precedents, often to the consternation of other conservatives. (In a 2007 case, in which Roberts had twisted logic into a pretzel to avoid striking down the same provision of the McCain-Feingold law that finally fell in Citizens United, Justice Scalia chewed him out in a now famous footnote: “This faux judicial restraint is judicial obfuscation.”)

Just last term Roberts wrote an opinion managing to uphold for all practical purposes the Sarbanes-Oxley financial reforms of 2002, notwithstanding having identified a serious constitutional flaw embedded deep within its structure. Using seemingly liberal techniques, he rewrote the law to the degree necessary to save it. Similarly, he saved, by effectively rewriting, much of the controversial federal honest-services fraud statute — a favorite prosecutorial weapon against white-collar criminals. Justice Scalia wrote a heated dissent, joined by Justices Thomas and Kennedy, protesting that Roberts’ reading of the law was “not interpretation but invention.”

Most Court observers also now believe that fundamental New Deal precedents — granting Congress very broad powers to regulate the economy — are safe with the Roberts Court, notwithstanding Roberts’ unsettling “hapless toad” dissent of 2003. They point to a recent test of the limits of congressional power, decided last May, in which the statute in question was upheld by a comfortable 7-2 vote, with Chief Justice Roberts joining the four “liberal” Justices in the most “liberal” of the three opinions written. Still, with the many Obamacare cases working their way to the Court, we will be learning more about that toad soon enough.

At his core, Roberts is a conservative. In all the national security cases so far — involving Guantánamo detainees and the like — he has seemed willing to grant the President carte blanche to fight terrorism. At his Reagan Library speech in 2006 — as the Iraq war neared its nadir — Roberts made a veiled reference to the need to fight to bring freedom to other nations. Roberts, who credits Reagan with having freed Eastern Europe and the former Soviet republics from communism, mentioned how inspiring it was to see the piece of the Berlin Wall now on display at the Reagan Library.

“And it was torn down, by the way,” said Roberts pointedly of the wall. “It didn’t fall. It was torn down.”

Roberts is also likely to vote like a conservative if the Court eventually hears the constitutional showdown that Goldstein considers “possibly the case of the century”: the challenge to the constitutionality of California’s Proposition 8, the 2008 ballot initiative forbidding gay marriage.

Numerous gay-rights cases are now working their way through the lower courts, challenging, for instance, the federal Defense of Marriage Act (which says that if gay marriage is allowed in one state, other states and the federal government need not recognize those marriages) and state laws restricting gay adoption. The Prop 8 case will be the toughest case for the gay-rights side to win, Goldstein explains, because it asks the Court to do the most: Strike down a definition of marriage that has prevailed for most of the country’s history and that is still used in all but a handful of states.

“On the one hand,” says Goldstein, “is the Supreme Court going to get out in front, when the right hasn’t yet been extended by many states? On the other hand, you could say, is the Supreme Court going to have this as its legacy — something where 25 years, 50 years, 75 years later, we’ll look back and say, How could we have been so mindless in our hatred? What do you want history books to say?”

At Roberts’ confirmation hearings, one of the members of his family that he introduced to the Senators was a cousin named Jean Podrasky.

“I don’t know John that well,” says Podrasky, 46, in an interview with Fortune, “but he’s always been very kind to our family.” Roberts gave her a personal tour of the White House as a high school graduation present, she remembers.

Podrasky is gay, as Roberts knows, she says. She lives in San Francisco with her longtime girlfriend. Would she like to be able to get married someday?

“Yes.”

Has she ever discussed —

“I really would never disrespect him by asking him about his cases,” Podrasky says, interrupting.

Most Supreme Court advocates focus on Justice Kennedy as the likely pivotal vote in the gay-rights cases. But might Roberts also be persuaded to rule that homosexuals have the same right to get married that heterosexuals do?

“No,” Goldstein says. “The Chief Justice can say, ‘I certainly don’t agree with this differential treatment, but this is a social institution that has existed throughout the nation’s history, and I’m not going to go so far as to invalidate it.'”

What to expect from the Court and Roberts in the coming years?

Underlying all the vitriolic debates over the Roberts Court is a frustrating reality: There is no accepted methodology for deciding a constitutional case, and there never has been.

Everyone agrees that the Supreme Court should not overrule its precedents lightly, yet everyone also agrees that some precedents must be overruled. Likewise, everyone agrees that the Constitution does sometimes require unelected judges to strike down democratically enacted legislation, though everyone howls when his own ox is gored.

Constitutional interpretation has an irreducible Ouija-board element to it. All Justices insist that their rulings are determined by forces outside themselves — precedent, original intent, text, pragmatism, and other lawyers’ tools. Yet on the most socially divisive issues of the day, each Justice does very often arrive at conclusions that seem to coincide suspiciously with his or her personal preferences.

While nonlawyers may be quick to dismiss the whole process as a charade, most lawyers don’t. All the advocates interviewed for this article, and most (but not all) of the professors, insist that there is integrity to the Justices’ approaches and content to their asserted methodologies. After all, they argue, almost half the cases last term were decided 9-0, according to SCOTUSblog figures. While about one in five did end up 5-4, there were unexpected alignments in a third of those.

“These are complicated questions,” says one Supreme Court lawyer. Unfortunately, he says, we’ve gotten into a box where each side is constantly accusing the other of deciding cases based on their personal views, and that discredits the whole operation. “In fact, they’re hard questions. It doesn’t mean people are reaching bankrupt results. It just means they’re hard questions.”

Though the Roberts Court’s conservative majority should hold steady for another five years or more, in the event of tragedy it could change dramatically tomorrow.

“If Justice Scalia left the Supreme Court,” says Goldstein, hypothesizing, “and was replaced by [left-of-center appeals court judge] Diane Wood, there’s nothing in the world that John Roberts could do to hold his majority. You can be the most incredibly articulate, thoughtful, influential Chief Justice in the world, and if you don’t have the votes, you don’t have the votes.”

By the same token, if a liberal Justice were to be replaced by a conservative, that, too, could have unforeseen and dramatic consequences. On the one hand, Roberts could conceivably become a moderating influence on his conservative colleagues. On the other, the stronger majority might embolden him to “let go,” in the words of (liberal) Yale Law professor Bruce Ackerman, i.e., lead the Court more rapidly toward the right than it is currently proceeding. “Based on his track record so far,” says Ackerman, “I don’t know which way he’d go.”

While no one should count on Roberts’ metamorphosing into a liberal, the way Justice Harry Blackmun did over time, Roberts’ jurisprudence will probably continue to evolve.

What will certainly happen is that labels like “liberal” and “conservative” will become inadequate to describe the Court’s divisions on many key questions as they emerge — questions concerning technological threats to privacy and security; concerning jurisdiction in a global economy; concerning the application of intellectual-property laws to unforeseen technologies; and concerning issues that none of us can articulate yet.

When those tough questions of the future arrive, we’ll have the comfort of knowing that there will be a smart guy with intellectual integrity leading the Court that has to grapple with them. That’s everyone’s silver lining.

Doris Burke contributed to this article.