Joshua Roberts / Reuters

Updated at 11:30 a.m. ET on April 4, 2019.

Last year, as Americans prepared to celebrate Thanksgiving, John G. Roberts, the 17th chief justice of the United States, did something unprecedented in the history of the Supreme Court: He responded directly to a political attack by the president of the United States.

A couple of days before, a federal district judge in California had temporarily halted new regulations on applications for asylum by foreigners entering the United States. Judge Jon S. Tigar held that the restrictions contravened the actual requirements of the Immigration and Nationality Act, and thus could not go into effect.

“That’s not law,” President Donald Trump said of Tigar’s decision. “This was an Obama judge.”

Roberts had never shown any interest in taking a public part in America’s partisan wars; nonetheless, in a statement to Mark Sherman of the AP, Roberts contradicted Trump: “We do not have Obama judges or Trump judges, Bush judges or Clinton judges. What we have is an extraordinary group of dedicated judges doing their level best to do equal right to those appearing before them. That independent judiciary is something we should all be thankful for.”

Chief justices have often hated presidents, and vice versa. (The two Virginia cousins, Thomas Jefferson and John Marshall, shared a flamboyant mutual detestation.) But both sides usually maintain a kind of clenched-teeth public politesse. Perhaps the closest thing to the Trump-Roberts exchange is a letter dated March 21, 1938, from Chief Justice Charles Evans Hughes to Senator Burton K. Wheeler in response to President Franklin Roosevelt’s ill-fated Court-packing plan—and it’s not that close. Both sides of that debate were careful to pretend the dispute was about whether the Court was current in its work, rather than partisanship.

Despite his direct rebuke to Trump, however, it is not obvious that Roberts can or would resist the transformation of the Court into an extension of the Republican Party.

John Roberts is perhaps the most enigmatic figure in national politics and government today. As the crisis of American democracy engulfs the Court, now is a good time to ask who Roberts is and what he believes. Readers seeking answers to those questions should turn first to Joan Biskupic’s fine new biography of Roberts, The Chief: The Life and Turbulent Times of Chief Justice John Roberts. Biskupic, who has covered the Supreme Court for The Washington Post, USA Today, and Reuters, is now a full-time legal analyst for CNN. Her years of experience and scrupulous fairness have given her access to the Court’s inner circle—top appellate lawyers, lower-court judges, former clerks, some of the justices themselves, and even the chief—that provides the best view of Roberts we are likely to have for years to come.

Biskupic documents the career of a young conservative whose ideas were formed during the exhilaration of the “Reagan revolution”; in the four decades since, he seems (like the Bourbon dynasty in the apocryphal quote from Talleyrand) to have learned nothing and forgotten nothing.

Roberts is not a “movement conservative”; Justices Samuel Alito, Clarence Thomas, and Neil Gorsuch are proud members of the conservative Federalist Society and ostentatiously bask in its adulation. Roberts has never fully identified with the society and tends toward greater decorum in his public appearances. During his confirmation hearing, he described the work of an Article III judge in the American system as that of a baseball umpire who calls “balls and strikes,” rather than determining who scores and who wins. He strives publicly to cut a smaller-than-life figure.

Yet Roberts is absolutely not a legal technocrat who seeks to further only process and separation-of-powers values. Anyone who has studied the record knows that Roberts came to Washington with a set attitude on a number of core issues—hostile toward civil-rights statutes like the Voting Rights Act and affirmative-action programs; solicitous of wealth in areas like labor relations and campaign finance; deferential to executive and military authority and correspondingly contemptuous of the legislative branch; socially conservative on matters of reproduction and sexuality; antagonistic to environmental protection, economic regulation, and government health-care programs. His public career before rising to the bench was entirely devoted to extending the power of the executive branch—an instinct on display in his early memos in the Ronald Reagan White House and fully embodied in his obsequious 2018 opinion in Trump v. Hawaii, upholding the administration’s anti-Muslim “travel ban.”

The news coverage of Biskupic’s book has focused on her insider’s account of Roberts’s behind-the-scene maneuvers in National Federation of Independent Business v. Sebelius, the 2012 case that affirmed most of the Affordable Care Act. Roberts’s vote determined all elements of that case. He joined the four conservatives to hold that the act’s “individual mandate” (which required taxpayers to maintain health insurance on all members of their households) was an unconstitutional extension of the commerce power. At the same time, he joined the four liberals to hold that the same mandate was permissible as an exercise of Congress’s taxing power (households that did not maintain insurance had to pay an additional tax, and suffered no other consequence). He also forged a surprising alliance with Justices Stephen Breyer and Elena Kagan to invalidate the ACA’s Medicaid expansion.

The resulting opinion has the appearance of a brokered deal. As Biskupic writes, Roberts’s “moves were not consistent and his legal arguments were not entirely coherent. But he brought people and their different interests together. He acted, in short, more like a politician” than like a judge. But Biskupic’s account does not—as many conservative commentators do, without much evidence—attribute the “mandate-as-tax” argument to bad faith. The tax-power issue was fully briefed and argued, and a number of scholarly commentators had written that the mandate was a rock-solid use of the taxing power; I see no evidence in The Chief that Roberts himself did not believe it.

Roberts’s management of the health-care litigation will spark controversy for generations; Biskupic’s answers are the best picture we are likely to have until some posthumous papers are opened. But to me, the most illuminating detail of Biskupic’s biography is her reproduction of an essay by the 13-year-old Roberts seeking admission to an elite all-male Catholic prep school near his home in Indiana.

“I’ve always wanted to stay ahead of the crowd,” Roberts wrote. “I won’t be content to get a good job by getting a good education, I want to get the best job by getting the best education … I’m sure that by attending and doing my best at La Lumiere I will assure myself of a fine future.”

By the age of 13, most upper-middle-class Baby Boomers had learned the art of asking for social advantage only in terms of human progress. Roberts, refreshingly, eschewed any such cant; instead, he quite unself-consciously explained that the only question that mattered to John G. Roberts was doing the best job possible for the advantage of John G. Roberts.

Roberts excelled as promised—at La Lumiere, he was a star athlete and graduated first in his class. It doesn’t deprecate his intelligence to note that this sort of class stardom, even for the gifted, is often in large part a result of a student’s family, wealth, and health. Roberts, however, seems to credit his success as a reflection of his personal excellences. In a commencement speech at La Lumiere in 2013, he explained: “Unlike many other keys to success—intellect, talents, physical ability, health, looks, where you were born, into what sort of family, luck—persistence is entirely, entirely within your control.”* The story is still about him.

Roberts was originally named to the Court to replace retiring Justice Sandra Day O’Connor; it’s intriguing to speculate about what an Associate Justice Roberts would have been like. But the unexpected death of Chief Justice William H. Rehnquist persuaded President George W. Bush to move Roberts’s name into the slot for chief. Since his confirmation, he has seemed to take responsibility for the welfare of the high court and the federal judicial branch. In that capacity, Roberts exudes a quality of wary watchfulness, for all the world like a tight-lipped headwaiter supervising dinner rush at a four-star restaurant. On the bench, he is usually gracious and formal, but in oral argument, he can become visibly choleric with advocates who take the wrong side of one of the issues he cares about. He is witty, often drawing laughs from the audience without seeking to draw blood from the advocate who is the target of his humor. His prose style is direct and seldom unintentionally unclear, and some of his opinions are hilarious. In his majority opinion in Federal Communications Commission v. AT&T Inc., which rejected the notion that a giant public corporation is entitled to shield government contacts from disclosure as a matter of its “personal privacy,” he concluded: “We trust that AT&T will not take it personally.”

Despite his humorous side, he is nonetheless deeply concerned about the dignity of the organization; his quips are not shtick of the sort that the late Justice Antonin Scalia enjoyed. Indeed, Roberts seems to frown on that kind of judicial stand-up routine. On one memorable occasion, during arguments over the Affordable Care Act, Scalia likened Medicaid expansion to a famous Jack Benny radio routine: “‘Your money or your life,’ and, you know, he says, ‘I’m thinking, I’m thinking.’ It’s —it’s funny, because it’s no choice. You know? Your life? Again, it’s just money. It’s an easy choice. No coercion, right? I mean—right? Now, whereas, if—if the choice were your life or your wife’s, that’s a lot harder.” As the other justices began to pick up the joke, Roberts interrupted: “No, let’s leave the wife out of it.” Scalia continued to make jokes, and Roberts finally said, in the tones of an exasperated prep-school prefect, “That’s enough frivolity for a while.”

This theme—the chief’s identification with the Court and its image—takes us back to Roberts’s extraordinary rebuke of the president. In claiming there are no “Trump judges” or “Obama judges,” he defended a position that is difficult to sell publicly—and one he does not appear to believe.

On April 19, 1983, Roberts, a young government lawyer, wrote a memo to his boss, White House Counsel Fred Fielding. Chief Justice Warren Burger had recently proposed a new “national court of appeals” made up of sitting appeals-court judges, between the current circuit courts of appeals and the Supreme Court. The new tribunal would exist mostly to resolve splits among the existing courts of appeals; deciding these, Burger argued, had become burdensome for the high court. The new tribunal would sort out the annoying from the truly important, and pass only the latter on to the justices.

A committee of the Reagan Justice Department had recommended supporting the idea; Roberts, however, was appalled, because the new panel would be recruited from current appeals-court judges. In other words, Democratic appointees might serve on it:

The new court will assuredly not represent the President’s judicial philosophy—and will have the authority to reverse decisions from courts to which the President has been able to make several appointments that do reflect his judicial philosophy. Under the committee proposal a Carter-appointed judge … could write a nationally-binding opinion reversing an opinion by Bork, Winter, Posner, or Scalia—something that cannot happen now. [Emphasis added]

Roberts understood then and I daresay understands now that, just as we had “Reagan judges” and “Carter judges,” we do have “Trump judges” and “Obama judges,”and when he is not performing a role for the public, that phenomenon probably does not dismay him. That’s because, as I said, his views on the issues are not far from those of the administration. His contempt for Congress, for Democrats like Barack Obama, and for “liberal” lower-court judges is palpable. His eagerness to defer to a powerful, conservative chief executive—as in his glib majority opinion in the “travel ban” case—is intense.

Since the retirement of Justice Anthony Kennedy last summer, Roberts has become the Court’s “median justice,” the member whose vote will usually determine the outcome of a closed case. More than ever before, Roberts’s view of current politics and law carry enormous weight. Thus, for example, when the Fifth Circuit approved a Louisiana antiabortion “health” law almost identical to one that the Court had struck down in 2016, it was only Roberts’s decision to vote with the liberals that blocked that appeals-court panel from defying the Supreme Court. When a Texas state court appeared to be ignoring the Court’s instructions in a death-penalty case, Roberts joined the Court’s Democratic appointees to overrule its decision. A week later, he again joined the four liberals to stay the death sentence of an inmate so demented, he could no longer remember the crime he had committed.

Roberts, however, is not by temperament a “swing” justice. His hesitations about moving the Court (and the country) to the right, it appears, are largely a question of pace; he believes that it is better to proceed slowly toward dismantling the New Deal, legislative protection of civil and voting rights, environmental protections, the remaining regulation of campaign finance, and the remaining shreds of the right of reproductive choice.

This solicitude for constitutional etiquette and the nonpartisan image of the federal courts is the most important thing that separates Roberts from the Trump administration, the other four conservative judges, and the extremists ensconced by Trump on the lower courts. What these other players have coveted for a generation, and now have, is power, and they are eager to use it.

The administration and the lower courts are stuffing the Court’s in-basket with cases that beg the justices to scrap liberal precedents;  see, for example, this summary by Linda Greenhouse of the abortion rulings from the lower federal courts that approve direct assaults on reproductive choice—showing contempt for Roberts-style caution, and in effect daring him to cross party lines.

In the case of the Affordable Care Act, Roberts of course did cross party lines, interposing himself between the far right and victory in 2012. He was ostracized and ridiculed by his former allies, and denounced by Donald Trump before and during the 2016 campaign for his defection.

Now the Trump administration is going to offer the Roberts Court the opportunity to get back into line with right-wing ideology. A federal judge in Texas has held that the Affordable Care Act is unconstitutional after all, and Trump—unable to undo the act legislatively—will apparently ask the Court to deliver the coup de grace. “If the Supreme Court rules that Obamacare is out, we’ll have a plan that is far better than Obamacare,” he said Wednesday. Its fate is up to the Court yet again.

Roberts might have to decide whether to sacrifice his conservative credibility a second time to protect the Court from the opprobrium of scuttling the nation’s health-care system. There’s little doubt that the other four conservatives would be delighted to take the act down, consequences be damned. Adding complexity: By the time the case reaches the Supreme Court, Roberts may no longer even be the swing vote. It’s quite possible that Trump will fill another Supreme Court vacancy before 2021. If that happens, or if Trump is reelected, Roberts will assuredly have to choose either to join his Court’s rapid move to the right or to condemn himself to irrelevance. His record suggests he is unlikely to remain a solitary figure seeking to block the triumph of legal conservatism.


* This article originally misidentified the school at which Roberts gave his 2013 commencement speech.

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