Here’s something you may not know unless you’re part of the insular world of Federalist Society shindigs or closely follow the Supreme Court: Legal conservatives of a certain stripe don’t like Chief Justice John Roberts.
Despite being nominated by George W. Bush and despite his previous job as a clerk for conservative stalwart William Rehnquist, Roberts has few allies among the people you might expect to champion him. I don’t mean in a behind-his-back, frenemy sort of way. It’s more of an all-out “you can’t sit with us” Regina George in “Mean Girls” way. They don’t like the reasoning in his legal opinions. They don’t like his style of writing in legal opinions. They don’t think his jokes from the bench are funny. They think he’s arrogant, self-important and, well, “chiefy.” In short: They don’t think he’s one of them.
Take this scene from a few years back. A half-dozen or so men and women in business attire file into the Mayflower Hotel. About six blocks from the White House, the place is about as old-school Washington as you can get. Dark corners. High-backed leather booths. Top-shelf brown liquor bottles glow on a well-lit shelf above the bar. The men and women, all conservative legal scholars — the kind that Republican presidents turn to when it’s time to nominate judges — sip scotch and pinot noir and engage in a parlor game. Who would you rather have on the Supreme Court today: Chief Justice John Roberts or Harriet Miers — the long-forgotten Bush nominee booted from confirmation after senators deemed she didn’t have the constitutional law chops. The laughter that booms through the Mayflower bar makes the answer clear. At least Miers would vote “the right way.”
I talked to more than a dozen former clerks and colleagues going back to the Reagan administration, as well as court watchers and leaders in the conservative legal movement to try to elaborate on why Roberts has become persona non grata to many on the right. Though he rolled in on the high tide of the conservative legal movement — under the auspices of a conservative White House just as the enormous influence of the Federalist Society was coming into full view — to many of the conservative legal observers I interviewed, Roberts seems more concerned with protecting the court’s reputation than interpreting and applying the law. Most of the people I spoke with did so on condition of anonymity — D.C. is a small town after all. As is the custom, the chief justice himself declined to comment.
While his harshest critics believe that he is undermining the rule of law and further politicizing the court others can’t help but see something more noble in his efforts to hold together one of America’s most important institutions, a last bulwark in preventing the court from descending into rank partisanship. On one point, everyone seemed to agree: John Roberts has his own way of putting the “chief” in chief justice.
In 2010, observers noticed something odd in the standard court press release announcing the newest justice: “Elena Kagan will be sworn in as the 100th Associate Justice of the Supreme Court.” (Emphasis added.) Just the year before, Sonia Sotomayor was announced as the 111th justice to the Supreme Court. But, according to multiple people I spoke with, the chief justice thought the distinction important enough to order the change himself. Indeed. The Supreme Court website currently says, “The Honorable John G. Roberts, Jr., is the 17th Chief Justice of the United States, and there have been 103 Associate Justices in the Court’s history.”
The change was much noticed inside the court, ruffling his colleagues as well. When Roberts joined the court as chief justice in 2005, the other eight justices had served together at that point for 11 years and some for longer — then-justices John Paul Stevens and Sandra Day O’Connor had served together since she joined the court in 1981. Roberts hadn’t been promoted to chief from the associate position as predecessor Chief Justice William Rehnquist had. He’d only even been a judge for two and a half years at that point. And now this upstart justice wasn’t just changing a line in a press release; he was announcing that he stood somehow separate from them.
But what if John Roberts was trying to explain his own judicial philosophy? Perhaps he changed the website because, in his view, lumping together the jobs of chief justice and associate justice is like comparing the attorney general to the postmaster general.
I’ve puzzled over Roberts and the way he operates on the court myself. As a first-year law student, I joined the Federalist Society in the midst of the Roberts nomination. By my second year, I was elected president of the Harvard Federalist Society and later clerked for Edith Jones, a Federalist Society mainstay considered by many to be one of the most conservative judges in the country.
By statute, the chief justice is chancellor of the Smithsonian, chairman of the judicial conference and — as we’ve been reminded recently — is constitutionally charged with presiding over an impeachment trial of a sitting president in the Senate. And as Roberts is fond of saying, “the most important difference is that I get 10,000 extra dollars.”
The role of a chief justice is best described as primus inter pares — first among equals. He may only have one vote, but he opens and moderates the conversation in the justices’ internal deliberations after a case is heard. If he is in the majority, he alone decides which justice writes the opinion — a process he has said he enjoys and describes as “a riddle or a puzzle to try to get everything to fit together.”
If a screenwriter tried to sell a script with a fictional John Roberts figure as chief justice, it would likely be rejected as a little too on the nose. After graduating from Harvard Law School and clerking for then-Associate Justice William Rehnquist, a young John Roberts was hired into the Reagan administration, becoming a favorite of Attorney General William French Smith before ascending to the deputy solicitor general role under Ken Starr during the elder Bush’s presidency. In private practice, he was and is considered the best Supreme Court advocate of the modern era.
It’s not just his resume. His piercing blue eyes, strong jawline, dimpled chin and perfectly coiffed hair made him look like a Federalist Society lab experiment titled “judicial conservative.” As he sat across the dais from the grizzled senators in a town that is often referred to as “Hollywood for ugly people,” he stood out.
If they ever do make a movie about John Roberts from those days, he could easily be played by Jeremy Northam, who, in the Showtime series “The Tudors,” played Thomas More — another lawyer who found his conscience did not fit in too well with the politics of his era.
Roberts wasn’t the favored choice among legal conservators, especially members of the Federalist Society, which law students had founded in 1982 and was coming of age by 2005. It was no longer a few acolytes of Justice Antonin Scalia in a basement at the University of Chicago. By the time Roberts was nominated that fall, the Harvard chapter alone boasted 500 members and thousands of lawyers, judges and academics from around the country attended the national conference. Out of its awkward adolescence during the late ’90s — when Starr’s team comprised members the likes of Alex Azar, Rod Rosenstein and Brett Kavanaugh — the Federalist Society finally had an opportunity to weigh in on a Supreme Court nomination during a friendly administration.
It came down to two people: John Roberts and Michael Luttig. They were the same age. They’d both clerked on the Supreme Court and worked in the Reagan administration, but Luttig was clearly the more impressive of the two on paper. He’d been a federal appellate judge for 14 years by that point, after being nominated when he was only 37 years old. Roberts had been nominated back then but the Democratic-controlled Senate never even moved to vote for his confirmation — perhaps giving a false sense that he’d been blocked because of his conservative credentials. Nearly every single one of Luttig’s clerks had gone on to work for justices Scalia or Clarence Thomas — a singular sign that Luttig himself was destined to join them.
By the time he was nominated to the Supreme Court, Roberts had only been on the D.C. Circuit for two years. His closest brush with hot-button constitutional issues was a case about a 12-year-old girl handcuffed for eating a french fry on a subway platform. But Bush himself was highly involved in the process and after meeting with both men, it wasn’t a close call. He “fell in love with John Roberts,” said one person closely involved in the process.
In an era in which they needed 60 votes in the Senate, it was a no-brainer. Roberts would shine on camera as “the golden boy from Bethesda,” said David Lat, the founder of Original Jurisdiction, a newsletter and website about law and the legal profession. Passed over for the main event and increasingly frustrated with the Bush administration, Luttig left the bench altogether the next year.
After it became fait accompli, the conservative legal eagles in D.C. gave breathless statements to the press. Ted Cruz — who had clerked for Luttig — wrote that Roberts was “undoubtedly a principled conservative,” a “brilliant” lawyer, who would “carefully, faithfully apply the Constitution and legal precedent.”
Behind closed doors, they were less certain. “There were enough warning signs that smart people in the White House detected it,” added Lat.
“People were concerned he was a squish but there was no real way to know,” said a person who was involved in his confirmation. “We had people at the Reagan library going through everything they could find.” There just wasn’t evidence either way. “He was … sassy … and some of his memos were hysterical from those days,” this person continued. “But the thing that gave me pause: He was just too slick. He had so carefully cultivated an image to ensure confirmation.”
Conservatives are associated with two methods of interpretation: originalism and textualism. Originalism is considered “the one true faith” for legal conservatives, as one longtime Supreme Court advocate put it. It is the idea that, according to Scalia, the Constitution “means today not what current society, much less the court, thinks it ought to mean, but what it meant when it was adopted.” Textualism is another conservative methodology — as textualist and 5th Circuit Judge Don Willett described it, “Text is the alpha and the omega of the interpretive process.” The two schools aren’t in tension exactly, but they aren’t the same either. An originalist is always a textualist, but a textualist doesn’t necessarily have to be an originalist.
And so this brings us to the question at hand: What is the judicial philosophy of John Roberts? At his confirmation hearing, he described the role of a judge “to call balls and strikes, and not to pitch or bat.” Conservatives at the time interpreted it as code decrying the liberal methodology of judicial activism, and so did liberals. It was assumed he’d be no different than his conservative brethren already on the court: Scalia and Thomas.
Then came the Affordable Care Act.
In 2010, after Obamacare went into effect, 26 states sued the federal government, arguing that the individual mandate — which required those who failed to purchase and maintain a minimum level of health insurance to pay a tax penalty — exceeded Congress’ constitutional power “to regulate commerce … among the several states.”
As the case wound its way through the courts, it became clear it would be decided in the run-up to the 2012 presidential election and became a flashpoint for both sides. President Barack Obama didn’t hesitate to weigh in — signaling that he would run against the court itself if his signature legislation wasn’t upheld in its entirety.
After oral arguments in March, CBS News reported, the chief had sided with his conservative colleagues, wanting to strike down the mandate. But by May, a steady drumbeat in the press and from the Oval Office warned of “damage to the court” — and to Roberts’ reputation — if the court were to strike down the mandate. He switched his vote.
He announced the opinion of the court in June 2012 — just over four months before the 2012 presidential election. His majority opinion upholding the law was joined by Justices Ruth Bader Ginsburg, Stephen Breyer, Sonia Sotomayor and Elena Kagan — his first time siding with the four Democratically appointed justices in a 5-4 decision — but his reasoning stunned even the closest court observers.
“The way Roberts delivered his bench statement … the guys from the SGs (solicitor general’s) office thought they’d lost,” said someone who was in the courtroom that day. “Their body language looked crestfallen. And then he said, ‘However.’”
Roberts wrote that Congress did not have the power to compel people to buy health insurance under the commerce clause but that the mandate was a lawful exercise of their taxing power, despite Obama himself denying that the mandate was a tax back in 2009.
The outrage from the right was immediate and it burned hot. “We had not yet experienced the kind of betrayal from someone who looked the part,” said one person involved in the chief justice’s confirmation.
“Obamacare was where he announced to the world that he was willing to base his vote on an analysis that he couldn’t possibly have arrived at but for the overriding influence of some felt obligation to protect the institution by controlling the outcome of the decision,” as one legal conservative said.
But then, three years later he not only sided with the dissenting conservatives in the landmark 5-4 ruling that the 14th Amendment required the legalization of same-sex marriage, he also did something he’d never done before: He read out loud from his dissenting opinion, a rare act reserved only for the most strongly held disagreements.
“This Court is not a legislature,” he wrote. “Whether same-sex marriage is a good idea should be of no concern to us. Under the Constitution, judges have power to say what the law is, not what it should be.”
In 2016, he voted with the conservative dissenters to uphold a Texas law that would have restricted access to abortion facilities in the state. Four years later, he flipped sides to join the liberal justices to strike down a Louisiana abortion law nearly identical to the Texas one he’d just voted to uphold.
He upheld President Donald Trump’s highly politicized travel ban in 2018. But then he refused to allow the Trump administration to add a citizenship question to the census or roll back the Obama-era Deferred Action for Childhood Arrivals executive order, holding that the Trump administration had failed to give clear enough reasons for the rollback in its rescission letter and that it would need to issue a new letter.
“The chief takes seriously his role as the keeper of the Supreme Court flame,” Starr, Robert’s old boss, told me. “I think that effort to protect the institution may explain some of his more controversial decisions.”
One former Roberts colleague put it more bluntly: “He has very deliberately and purposely chosen not to bring a judicial philosophy to his position of chief justice. If one has no judicial philosophy or chooses not to bring it to the job, he is ‘free’ to decide each case as he wants, untethered and unconstrained by any method of principled decision-making. The law becomes whatever that one wants it to be.”
Predicting the outcome of cases became even harder. While the other justices often show their cards in the questions they ask the advocates for each side, Amy Howe, co-founder of Scotusblog, noted that the chief is consistently the “hardest to read at oral argument” and pondered whether “minimalism is a philosophy or strategy.”
The golden boy from Bethesda was now an enigmatic swing vote on the court.
In the run-up to the 2016 election, Roberts seemed to be hedging his bets, assuming he was just as likely to be the chief of a liberal majority court as a conservative one. He certainly looked prescient. “The chief was sitting there thinking, ‘I’m going to be on the losing end of a 5-4 court, and I need to figure out a way to retain my influence with the people who may end up becoming the five,’” as one former clerk described the sentiment.
But the shadow of John Roberts loomed large in the judicial selection process for the Trump administration. “The goal was to find people who would not be like him,” one White House official put it. “The utter frustration around Roberts meant we had to get it right this time.”
Once Anthony Kennedy retired, Roberts would be the swing vote and so the pick to replace Kennedy needed to be reliably conservative but also able to woo Roberts. Someone like Brett Kavanaugh. “A virtue of (Kavanaugh) was the perception that he would have a meaningful relationship with the chief and keep him on the reservation,” as someone involved in Kavanaugh’s selection put it.
Kavanaugh was perfect — for starters, he’d been on the Bush team that worked to confirm Roberts as chief justice in 2005. During Kavanaugh’s time on the D.C. Circuit, a good portion of the chief justice’s clerks had worked for him at the lower court — a reliable sign of respect and friendship between a Supreme Court justice and his “feeder judge.”
Kavanaugh’s brutal confirmation process only further cemented the relationship. The chief gave a speech just a few weeks later and opened his remarks by “touching upon the contentious events in Washington of recent weeks” going on to quote the newly sworn-in Kavanaugh that “we do not sit on opposite sides of an aisle, we do not caucus in separate rooms, we do not serve one party or one interest, we serve one nation.” And when Sen. Chuck Schumer attacked justices Kavanaugh and Neil Gorsuch by name on the steps of the court, the chief issued a rare public rebuke, saying “threatening statements of this sort from the highest levels of government are not only inappropriate, they are dangerous.”
And it seemed to be going to plan. In his first full term on the court, Kavanaugh voted with Roberts 94% of the time — more than any other pairing — and put the two of them in the majority more than any of the other justices as a new conservative middle. In that first year, they joined with the conservatives to uphold partisan gerrymandering and they joined with the liberals to stay the execution of a Buddhist man who wanted his spiritual adviser to be present — arguably a win for religious liberty even if it was a liberal one.
But when liberal icon Ginsburg died on a Friday night in September 2020, everything stopped in Washington.
Scalia had died with nine months until the 2016 election — more than enough time to confirm the judge nominated as his successor, Merrick Garland. Republicans controlled the Senate, however, and then-Majority Leader Mitch McConnell wouldn’t budge. It was an election year, Republicans argued, and the voters should get to decide, knowing that they had nothing to lose if Hillary Clinton won — a liberal vote was a liberal vote even if she picked someone to the left of Garland — and everything to gain if an open Supreme Court seat motivated even a few more Republicans to head to the polls in November.
Now, in 2020, history was repeating itself, except only 45 days remained until the election. “John Roberts is what got us Amy Coney Barrett,” a White House official involved in confirmations told me. If conservatives had already had a reliable fifth vote on the court — once Kavanaugh had replaced Kennedy two years earlier — Republicans may not have been able to overcome the political cost of hypocrisy for filling Ginsburg’s seat so close to a presidential election.
Roberts’ days as the fifth vote were over.
With the Biden administration under pressure to “pack the court” by adding new justices to counter the conservative majority, the institution hasn’t been so imperiled since the days of Franklin Delano Roosevelt — when the progressive president felt a conservative court was unfairly striking down his ambitious New Deal programs and threatened to add liberal justices. Roberts may have hoped that his most recent abortion and DACA cases would deny the left the rallying cry they needed to get buy-in from Democratic leadership. So far his bet is paying off — President Joe Biden has only gone so far as to create an exploratory commission, and most political pundits agree that little else will come of it.
“The chief has guided the court in such a way that makes it hard for one party just to say this place has become absolutely political and we need to change it,” one former clerk said. “This attempt (to add seats to the court) has died, so that may not be unrelated to his stewardship of the court.”
But that was before Barrett joined the court and the chief became the superfluous sixth vote. And before Roe v. Wade was on the chopping block. In the last months of the term, the court has agreed to hear its first Second Amendment case in a decade and to decide whether Mississippi’s ban on abortions after 15 weeks is constitutional — a direct challenge to Roe v. Wade. Roberts’ court may be set to decide the most controversial case since Bush v. Gore next year. And it’s not at all clear where the chief will land — or whether his voice will matter.
While the right may hope his vote is irrelevant, he has handed them plenty of wins through the years. And even his most heretical opinions provided plenty for conservatives to feast upon. Sure, he upheld the individual mandate in Obamacare, but only after narrowing Congress’ use of the commerce clause for the first time in nearly two decades. He struck down Louisiana’s abortion restrictions but, in doing so, he also considerably narrowed the court’s legal test on abortion — arguably the biggest Supreme Court win for the anti-abortion movement in a decade. .
As one longtime advocate explained it: “He is trying to protect the court as an institution while doing the least amount of violence to conservative principles.”
But elevating such institutional considerations comes with a cost. If the political branches see the lengths to which the chief is willing to go to keep the court out of the political fray — as they surely do — then they’re further incentivized to ratchet up their threats to do just that. And as the pace of credibility-preserving outcomes necessarily picks up to meet the ever-increasing peril, the actual credibility of the court may well decrease.
“The chief justice has made abundantly clear that foremost in his mind is whether a particular decision the court makes or does not make will further or lessen the public’s perception of the Supreme Court as essentially a political institution,” one longtime leader within the conservative movement told me. “This has predictably had the polar opposite effect from what the chief mistakenly thought; the court is perceived as much more political today than when he arrived.”
John Roberts’ judicial legacy will be written by history — perhaps by the 18th or 19th chief justice who can look back and definitively answer whether Roberts saved the rule of law by shielding it from the harsh winds of our early-21st-century political polarization or whether his political machinations undermined the very institution he was charged with protecting.
But he doesn’t seem too concerned at this point. After all, he’s still got a job to do. He eats salads on most weekdays and indulges in a nearby burger and milkshake when he works on the weekends. The wit that he displays on the bench is even more apparent in chambers. He’s quick to return phone calls and emails from former clerks eager to tell him about their latest career moves or family updates. He tells anyone who visits his office about the couch in his inner office where John Quincy Adams died.
Most Americans, of course, will never know that John Roberts, and he seems fine with that.
In a rare public appearance, Chief Justice Roberts said that he wasn’t bothered that Americans couldn’t name justices on the court. “In some sense, I think that’s probably a very good thing. We wear black robes to convey the notion that our individual views (and) personality (do) not have anything to do with the function we have to play in terms of coming to a correct decision on the law.”
On his deathbed, perhaps the chief justice will say some version of what Thomas More said before him: “I die the Law’s good servant, but the Court’s first.”
Sarah Isgur has worked on three presidential campaigns and in all three branches of the federal government. She most recently served in the Department of Justice as director of the Office of Public Affairs and senior counsel to the deputy attorney general.