The Chief: The Life and Turbulent Times of Chief Justice John Roberts by Joan Biskupic Basic
Denise Nestor

Two years ago, Chief Justice John Roberts gave the commencement address at the Cardigan Mountain School, in New Hampshire. The ninth-grade graduates of the all-boys school included his son, Jack. Parting with custom, Roberts declined to wish the boys luck. Instead he said that, from time to time, “I hope you will be treated unfairly, so that you will come to know the value of justice.” He went on, “I hope you’ll be ignored, so you know the importance of listening to others.” He urged the boys to “understand that your success is not completely deserved, and that the failure of others is not completely deserved, either.” And in the speech’s most topical passage, he reminded them that, while they were good boys, “you are also privileged young men. And if you weren’t privileged when you came here, you’re privileged now because you have been here. My advice is: Don’t act like it.”

As Justice Brett Kavanaugh’s maudlin screams fade with the other dramas of 2018, Roberts’s message reveals a contrast between the two jurists. Whatever their conservative affinities and matching pedigrees, they diverge in temperament. The lingering images from Kavanaugh’s Senate confirmation hearing are of an entitled frat boy howling as his inheritance seemed to slip away. By contrast, Roberts takes care to talk the talk of humility, admonishing the next generation of private-school lordlings not to smirk.

The chief justice also carries himself in a manner that reflects his advice. He chooses his words carefully. He speaks in a measured cadence that matches his neatly parted hair and handsome smile. He is deliberate and calm, not just in his public remarks but in his work as a judge—and as a partisan. Roberts declines to raise his voice or lose focus, because he understands politics as a complex game of strategy measured in generations rather than years. He also recognizes, but will never admit, that although politics is not the same thing as law, the two blend together like water and sand. More than 13 years into his tenure as chief justice, Roberts remains a serious man and a person of brilliance who struggles, under increasing criticism from all sides, to balance his loyalty to an institution with his commitment to an ideology.

Basic

The first biography of Roberts has arrived, Joan Biskupic’s The Chief. It will not be the last. A well-reported book, it sheds new light but is premature by decades. (Biskupic is a legal analyst for CNN.) As our attention spans dwindle to each frantic day’s headlines, we can forget that the position of chief justice is one of long-term consequence. Only 17 men have filled that role, and they have presided over moments of national crisis, shaping our government’s founding structure (John Marshall), hastening its civil war (Roger Taney), responding to the Great Depression (Charles Evans Hughes), and enabling the civil-rights revolution (Earl Warren).

Roberts seems ever likelier to face an equally daunting test: confronting a president over the value of the law itself. A staunch conservative, he has broken ranks with the right in a major way just once as chief justice, by casting the deciding vote to save the Affordable Care Act in 2012. What will Roberts do if the clerk calls some form of the case Mueller v. Trump, raising a grave matter of first principles, such as presidential indictment and self-pardon? He portrays himself as an institutionalist, but we do not yet know to what extent this is true. He must necessarily prove himself on a case-by-case basis, which injects a note of drama into his movements. Roberts is the most interesting judicial conservative in living memory because he is both ideologically outspoken and willing to break with ideology in a moment of great political consequence. His response to the constitutional crisis that awaits will define not just his legacy, but the Supreme Court’s as well.

As a young man, Roberts was the anti-Kavanaugh. Although he, too, attended a prestigious Catholic prep school—La Lumiere, in northern Indiana—Roberts had no time for drinking parties. His life as a young man is a story of purpose and industry. He studied constantly, acquired Latin, graduated first in his class, and entered Harvard as a sophomore. He planned to become a history professor. Still, however humbly he absorbed life’s blessings, Roberts, the son of a steel executive, grew up in a narrow world that made few calls upon his empathy. In personality he was quiet and serious, seeing much but revealing little. His displays of budding conservatism were rare but sharp-edged, as in a high-school-newspaper editorial objecting to the admission of girls.

After graduating from Harvard Law School, Roberts clerked for two notable federal judges: Henry Friendly of the U.S. Court of Appeals, and then William Rehnquist of the Supreme Court. Friendly, a revered jurist known for his scholarly opinions, seems to have taught the young man form; Rehnquist, a partisan conservative, taught him substance. Biskupic quotes repeatedly from Roberts’s correspondence with Friendly after Roberts entered Ronald Reagan’s administration in 1981. “This is an exciting time to be at the Justice Department, when so much that has been taken for granted for so long is being seriously reconsidered,” he wrote. Surrounded by other Republicans after years in liberal Cambridge, Roberts displayed fierce conservatism on matters of legal policy. He wrote strident memos on voting rights, school prayer, abortion, and women’s equality. Advancing quickly, he went on to hold prestigious legal positions in Reagan’s White House and in the solicitor general’s office under President George H. W. Bush.

In the 1990s and 2000s, Roberts rose to the height of private practice as an appellate advocate. Biskupic writes that “with his deep, methodical research and direct, unadorned rhetoric,” he was uncommonly effective arguing before the Supreme Court. Biskupic ably conveys Roberts’s appeal, as well as her own skepticism:

Roberts does have a way of sounding eminently reasonable. He speaks with a steady voice and in clear, direct sentences. He argues with a thoughtful tone. His confidence is manifest, but never brazen. Roberts almost never looks flustered, and he never stammers. He prepares intensively for every public appearance he makes, working both on the substance of what he will say and on his presentation.

These habits (along with a brief stint, beginning in 2003, as a federal appeals-court judge) all but guaranteed Roberts’s confirmation after George W. Bush nominated him to the Supreme Court in 2005. With his baseball metaphors, charming family, and utter mastery of constitutional law, he was irresistible. Republicans fawned over his credentials and politesse, and even many Democrats conceded that he was a rare talent. Political handlers have advised subsequent nominees to study the tapes of Roberts’s confirmation hearings and do their best to sound like him. No one has come close.

As chief justice, Roberts has proved a committed conservative whose defection in the 2012 Obamacare decision and then in a 2015 follow-up case somehow rendered him permanently squishy to true believers. He has sided with the right in 87.5 percent of 5–4 decisions, according to a 2015 article in the Journal of Legal Studies. Roberts voted to deregulate campaign finance in Citizens United v. Federal Election Commission, to constitutionalize gun ownership in District of Columbia v. Heller, and to restrict school-integration plans in Parents Involved in Community Schools v. Seattle School District No. 1. The most significant, and destructive, decision of Roberts’s career so far was his 2013 opinion striking down the heart of the Voting Rights Act, in Shelby County v. Holder. Despite his frequent invocations of judicial modesty, Roberts has been willing to reach such results by overturning established precedents, and by deciding matters the parties have not raised.

Yet since 2012, the right has distrusted him. Roberts’s shocking defection in that year’s Affordable Care Act case roused anger and feelings of betrayal in a conservative movement increasingly bent on ideological purity. Even as he writes breathtakingly conservative opinions, Roberts’s mere willingness to pay lip service to institutional values such as restraint and nonpartisanship now arouses suspicion. In keeping with the fighting spirit of the times, members of the Republican base demand a warlike posture from the chief justice when strategic patience would better serve their interests. Perhaps the long and painful history of unreliable conservatives nominated by Republican presidents is to blame. Two of the most recent disappointments, David Souter and Anthony Kennedy, began to stray by joining a centrist triad in a politically sensitive case—just like the chief justice.

Biskupic reports in detail for the first time on the machinations of the Obamacare case, revealing that Roberts started out in a different place. She writes that he initially voted with the four other conservatives to strike down the ACA, on the grounds that it went beyond Congress’s power to regulate interstate commerce. Likewise, he initially voted to uphold the ACA’s expansion of Medicaid. But Roberts, who kept the opinion for himself to write, soon developed second thoughts.

Biskupic, who interviewed many of the justices for this book, including her subject, writes that Roberts said he felt “torn between his heart and his head.” He harbored strong views on the limitations of congressional power, but hesitated to interject the Court into the ongoing health-insurance crisis. After trying unsuccessfully to find a middle way with Kennedy, who was “unusually firm” and even “put off” by the courtship, Roberts turned to the Court’s two moderate liberals, Stephen Breyer and Elena Kagan. The threesome negotiated a compromise decision that upheld the ACA’s individual mandate under Congress’s taxing power, while striking down the Medicaid expansion. Future scholars will endlessly probe this fascinating moment in judicial history, but Biskupic deserves credit for writing the first draft.

Why did Roberts do it? Biskupic does not profess to have the answer.

Perhaps Roberts’s move was born of a concern for the business of health care. Perhaps he had worries about his own legitimacy and legacy, intertwined with concerns about the legitimacy and legacy of the Court. Perhaps his change of heart really arose from a sudden new understanding of the congressional taxing power.

This much at least can be said: Roberts declined to join the other four Republican-appointed justices to invalidate the key legislative achievement of a Democratic president during an election year. Such a move would have further eroded the Court’s claim to transcend politics after the image-shattering decisions in Bush v. Gore (2000) and Citizens United (2010). Notably, although the Affordable Care Act was highly politicized, the provision of health care is not a matter of bedrock conservative judicial philosophy, as abortion, affirmative action, and the right to bear arms are. Maybe this freed Roberts to prioritize the Court’s reputation over the right’s immediate partisan interests. A future conflict with the executive branch over the nature of obstruction of justice or the reach of criminal laws may fall into a similar category. Only John Roberts can know.

For all his ability and charm, Roberts has so far been an uneven leader. He strives for unanimity and, in public remarks, extols the benefits of consensus for the Court’s reputation and collegiality. But he presides over a deeply divided Court that descends into rancor ever more frequently. Justices Ruth Bader Ginsburg and Sonia Sotomayor have protested the conservative majority’s decisions in bitter and even personal terms. Bad blood is evident between several members: Kagan and Samuel Alito bickered like a divorced couple over a 2014 First Amendment case. Biskupic may go too far when she writes of Roberts’s “secretive ways” or of his “continued inability to win the personal confidence of his colleagues.” Yet, with the exception of a series of unanimous decisions in 2016, when the Court had only eight members, Roberts has generally been unwilling to forgo conservative victories for the sake of consensus. As Eve knew, sometimes the fruit is just too tempting.

It is remarkable to think that the Roberts Court’s blockbuster decisions on gay rights, campaign finance, and immigration may be small potatoes compared with far more dramatic matters to come. Perhaps there will be no constitutional clash between the Court and the presidency. But if it does arrive, Roberts, as the Court’s leader and now the most centrist of its conservatives, will be the justice to watch. His legendary poise will count for only so much. One of his colleagues on the appellate bench told Biskupic, “John Roberts has always seen everything with pristine clarity, and almost instantly.” If that is true, then in his abilities, and his burdens, Roberts stands alone.


This article appears in the March 2019 print edition with the headline “The Chief Justice’s Secret.”

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