Politics Foreign Affairs Culture Fellows Program

Sonia Sotomayor, Boomer

A sense of grievance turned the People’s Justice into a bully.

In 2013, the conservative bloc on the Supreme Court was ready to issue a ruling in Fisher v. University of Texas that would have limited the use of race in college admissions, when Justice Sonia Sotomayor persuaded Anthony Kennedy to change his vote. It was not the cogency of her arguments that persuaded him.

Kennedy had been a reliable vote against affirmative action throughout his twenty-five years on the bench, as recently as Grutter v. Bollinger in 2003, when he dissented from Sandra Day O’Connor’s opinion upholding affirmative action as long as race is only one narrowly tailored factor out of many. But sometime between oral argument on October and the announcement of the opinion on June 24, Sotomayor circulated a blistering draft dissent that made Kennedy change his mind.

That draft dissent has never been published, but when the veteran Supreme Court reporter Joan Biskupic started asking around about what had happened with Fisher—which Court watchers noticed was not announced until the last week of the term, months after the other cases argued in October had been decided—she heard from insiders that “I would soon see a version of it.”

Apparently the text of that draft was repurposed for Sotomayor’s dissent in Schuette v. Coalition to Defend Affirmative Action (2014), which upheld a Michigan state constitutional amendment banning racial preferences. Justices don’t always read their dissenting opinions aloud from the bench when decisions are announced, but in Schuette, for the first time, Sotomayor read hers.

Her dissent begins with an introduction comparing the voters of Michigan to the white majority that imposed Jim Crow, a comparison that Justice Antonin Scalia, in his concurring opinion, called “shameful.” It crescendos to a deeply personal explanation of why her colleagues’ hopes for a color-blind solution to racial inequality are “out of touch with reality,” introducing the boomer vocabulary of therapy and trauma into the normally arid language of judicial opinion:

Race matters for reasons that really are only skin deep, that cannot be discussed any other way, and that cannot be wished away. Race matters to a young man’s view of society when he spends his teenage years watching others tense up as he passes, no matter the neighborhood where he grew up. Race matters to a young woman’s sense of self when she states her hometown, and then is pressed, “No, where are you really from?” regardless of how many generations her family has been in the country… Race matters because of the slights, the snickers, the silent judgments that reinforce that most crippling of thoughts: “I do not belong here.”

Some justices on the current Court respond badly to emotional blackmail. Chief Justice John Roberts was so incensed that he wrote his own two-paragraph concurrence entirely devoted to criticizing Sotomayor for attacking the majority in such personal terms (“People can disagree in good faith on this issue, but [it] does more harm than good to question the openness and candor of those on either side of the debate”). Scalia, as we saw, thought such histrionics disgraceful. 

But on Kennedy—the man who loved to be hailed as the conscience of the Court, who pondered tough questions by walking back and forth across his office courtyard in the pose of Rodin’s Thinker, the man to whom wags applied the term “the Greenhouse Effect,” after New York Times correspondent Linda Greenhouse, whose approval Kennedy craved—on Kennedy, it worked.

Those “slights” and “snickers” that say “I do not belong here” are a staple of Sotomayor’s public persona. Her memoir, for which she received a reported $1.175 million advance, is full of references to her insecurities. At lectures in front of middle schoolers, on The Daily Show, on The View (where the ladies addressed her as “Sonia”), Sotomayor reassures her audiences that even with all her accomplishments she still hears a voice in her head asking, “Am I really here? Do I really belong?” Like many boomers, Sotomayor has shaped her persona around a psychological narrative of personal growth, from self-doubt to self-acceptance.

When she was nominated as President Barack Obama’s first Supreme Court appointee, it was hoped that Sotomayor could become “the people’s justice.” Her biography was compelling: growing up poor in the Bronx, diagnosed with diabetes when she was seven, alcoholic father dead when she was nine, raised thereafter by her nurse single mother and loving abuelita. There was some controversy during her confirmation over a speech in which Sotomayor expressed hope that a “wise Latina woman, with the richness of her experiences, would more often than not reach a better conclusion than a white male who hasn’t lived that life.” 

Her defenders responded that the “wise Latina” quote was merely arguing for judges to draw on the richness of their diverse backgrounds. In her Schuette dissent, however, Justice Sotomayor showcased not the richness of her Latina background but only its resentments.

Hard as it may be for her to believe, Sotomayor is not the first Supreme Court justice to feel out of place. Charles E. Whittaker was appointed by Eisenhower, after Earl Warren, and his short tenure was blighted by his feelings of inferiority. He was not Hispanic, or female, or even Jewish. He was a straight white Protestant male from Kansas. But he had dropped out of high school at sixteen and gone to an unaccredited night school for his law degree, and colleagues like Felix Frankfurter and William O. Douglas intimidated him. “You know Charlie had gone to night law school, and he began as an office boy and he’d been a farm boy, and he had inside him an inferiority complex,” one justice told Earl Warren’s biographer. “He used to come out of our conferences literally crying…he’d say, ‘Felix used words in there I had never heard of.’ ” Eventually Whittaker had a nervous breakdown and resigned in 1962.

Coming from humble beginnings does not determine how someone will end up. Everything depends on how a person handles it. Harry Truman attended the same unaccredited Kansas City night school as Whittaker, before poverty forced him to drop out, and Truman turned out fine. A disadvantaged background made Charlie Whittaker a neurotic. It made Sonia Sotomayor a bully. The boomers’ preoccupation with oppression, identity, and grievance would create many bullies, because it turns out that thinking of yourself as a victim can make you heedless of the ways your actions victimize others.


Sotomayor learned early in life that something about her gave her the power to make authority figures hop. As a sophomore at Princeton, she and other members of the activist group Acción Puertorriqueña sent a formal letter of complaint to the federal Department of Health, Education, and Welfare accusing Princeton of not hiring enough Hispanics. “The facts imply and reflect the total absence of regard, concern and respect for an entire people and their culture,” she explained to The Daily Princetonian in May 1974. “In effect, they reflect an attempt—a successful attempt so far—to relegate an important cultural sector of the population to oblivion.” 

Within weeks, HEW sent a federal official to New Jersey to meet with Sotomayor and an associate provost, who agreed to send Sotomayor an official minority hiring plan by the end of June.

Looking back on those years in her memoir, Sotomayor describes her undergraduate experience as a struggle to fit in, but in activism she found a psychological reinforcement more potent than belonging: power. The tone of her letter was hardly ingratiating. By pre-boomer standards, it was abusive. But far from urging this intemperate full-ride scholarship student that she should make more of an effort to fit in, Princeton quickly hired a Latino assistant dean of students who was on campus in time to greet Sotomayor when she returned for her junior year in September.

Her complaint to HEW was not, strictly speaking, a protest. The officials who received it welcomed its message. So did Princeton. The minority hiring plan “would have been prepared and submitted whether or not there had been a student complaint,” an administrator admitted later. Shortly before Sotomayor sent her letter, the board of trustees had voted $200,000 to refurbish the Third World Center, the campus hub for minority student groups, including Acción Puertorriqueña. The university was not only willing but eager to meet activists’ demands. Any posture of protest on the students’ part was mere playacting.

Sotomayor encountered more resistance when she tried the same gambit at Yale Law School. At a recruiting dinner for law students in 1978, a partner from the firm Shaw, Pittman grilled her about affirmative action: “Do you think you would have been admitted to Yale Law School if you were not Puerto Rican? . . . Do law firms do a disservice by hiring minority students who they know do not have the necessary credentials and will then fire in three to four years? . . . Do you consider yourself culturally deprived?” 

No doubt he was testing her to see how she would react. When Antonin Scalia had a similar dinner with prospective employers at the Cleveland-based law firm Jones, Day shortly after graduating from Harvard Law, the partners hammered the devout Catholic on blue laws mandating Sunday shop closings, which Scalia was the only one at the table to support. “They really put it to him,” one of his hosts remembered, “and he handled it beautifully.”

Sotomayor did not accept her interrogation in a similar spirit. She filed an official complaint accusing Shaw, Pittman of violating Yale’s antidiscrimination policy and questioning their right to recruit on campus in the future. A faculty-student tribunal found in Sotomayor’s favor and demanded a letter of apology, which Shaw, Pittman sent and then redrafted in more abject terms when their first letter of apology was deemed inadequate by Yale officials. 

Funnily enough, when Sotomayor showed up for her one-on-one interview the day after the disastrous group dinner, the partner who had grilled her invited her to come to Washington for more interviews. He thought she had handled the questioning well.

The journey from Bronx housing project to Ivy League law school had taught Sotomayor resilience. But it also taught her that bullying would yield results, that she would never pay a price for acting out; on the contrary, that she would be rewarded. This was, in a way, an appropriate lesson for her to learn. She was about to enter a profession that made a decades-long mission of bullying America.


The United States has been known as a land of lawyers since the eighteenth century. Edmund Burke and Alexis de Tocqueville both remarked on it. But it was not until the boomer era that the profession really came into its own, thanks in part to the rise of public interest law, the legal equivalent of an industrial revolution.

In the first half of the twentieth century, a nonprofit with a name like the German Legal Aid Society could be assumed to provide pro bono legal work for indigent clients from the demographic group named in its title. The Mexican American Legal Defense and Educational Fund, founded in 1968, was more interested in changing the law, winning cases that would set far-reaching precedents. 

Eventually, many of the big public interest law firms stopped accepting routine cases lacking landmark potential. The purpose of public interest law at that point was to take the liberal eruptions of the Warren Court, which had caught the country by surprise, and make them routine. There were fifty full-time public interest lawyers in the country when Chief Justice Warren resigned in 1969. By 1975, there were six hundred.

Many of the great Warren Court cases were brought by independent individuals like Clarence Earl Gideon and Ernesto Miranda, whose cases were taken up by groups like the ACLU late in the process, if at all. The precedent-setting cases after 1970 were more likely to have been conceived, designed, and executed by nonprofit law firms from the very beginning. The Puerto Rican Legal Defense and Education Fund, on whose board Sonia Sotomayor served from 1980 to 1992, launched and won cases forcing New York to offer bilingual education in public schools, redraw city council districts, and print government forms in Spanish, all without going to the trouble of winning an election.

The industrial manufacture of left-wing precedents was not the practice of law as it had been known for centuries. Common law offenses like barratry and maintenance had to be thrown out the window. The purpose of those antique torts had been to prevent third parties from subsidizing legal action for purposes of their own, using the client as a cat’s-paw. Subsidizing legal action for purposes of your own, independent of your client’s, is what public interest law is. 

Traditionally, attorneys are not allowed to solicit clients but must wait for clients to come to them. This, too, is to ensure that cases are brought only by clients who are personally invested in the outcome and whose self-interest can be appealed to in reaching a reasonable settlement.

The Equal Employment Opportunity Commission, by contrast, used to send its lawyers around the country in the 1970s canvassing for plaintiffs who had been discriminated against at work. When the EEOC decided to go after a particular employer, it would put ads in the local paper inviting former employees to come and testify (and, of course, collect their share of the payout if the case was successful). The Supreme Court ruled in the 1978 case In re Primus that a lawyer for the ACLU was permitted to solicit clients by mail, contrary to bar regulations, because she did it for a political cause and not for her own profit. 

By the time the gay rights movement hit its stride at the turn of the century, no one any longer thought it odd that such far-reaching social changes should be accomplished through highly choreographed plaintiff selection and organized harassment of shop owners. The old Brandeisian notion that cases must involve an “earnest and vital controversy” arising naturally from the frictions of society was dead.

As judges came to decide more matters that had previously been left to elected politicians, the judicial process came to resemble politics in all its rowdiness. More than 500,000 pro-choice protesters descended on Washington in advance of the oral argument in Planned Parenthood v. Casey in 1992. This demonstration would have been recognized as inappropriate in an era when judicial impartiality was still taken seriously. If judges merely apply the law, it should not matter what half a million demonstrators think. 

The protesters’ show of force was rewarded. When the Casey decision came down, it explicitly grounded its refusal to overturn Roe in the need to protect “the people’s acceptance of the judiciary.”

The circus quality of modern Supreme Court nominations is a direct result of this politicization. Like public interest law, this spectacle is something genuinely new. For most of the Supreme Court’s history, nominees did not even attend their own hearings. The Left is to blame for the current state of affairs, and not just because it was Democrats who fired the first shot against Robert Bork in 1987 and launched the war of escalation that has led to the current stand-off. Empowering the judiciary to meddle deeper in politics in the name of constantly evolving constitutional rights is what has made the stakes of each nomination so high. The people who talk in lofty terms about the exalted role of judges in our democracy are the ones responsible for forcing the nomination process down in the muck.


Sotomayor did not enjoy her confirmation process. A White House “war room” is a grueling experience for any nominee, and Sotomayor did not approach hers in an obliging frame of mind. “There were private questions I was offended by,” she complained later. “I wondered if they ever asked those questions of the male candidates. But the society has a double standard.” 

In fact, Anthony Kennedy remembers being asked by White House lawyers when he first had sex and if he’d ever had an STD or dabbled in S&M, among other intrusive questions, and that was before the advent of 24-hour cable news when scrutiny of hearings was less intense. 

White House staffers also told Jeffrey Toobin of The New Yorker that Sotomayor resented being forced to prepare detailed answers on “the full range of constitutional law,” making her sessions “tense and laborious.”

To be fair to Sotomayor, she had a rougher confirmation than most. Her critics did not hesitate to criticize her in the most demeaning terms. “Bluntly put, she’s not nearly as smart as she seems to think she is,” Laurence Tribe told President Obama in a confidential memo that was later leaked. He wanted his Harvard Law dean, Elena Kagan, nominated instead, not just because she was smarter, but because she would have a better chance of persuading Anthony Kennedy to side with the liberals in cases where he was a swing vote. With Sotomayor, “her reputation for being something of a bully could well make her liberal impulses backfire and simply add to the fire power of the Roberts/Alito/Scalia/Thomas wing.”

Even more humiliating was Jeffrey Rosen’s hit piece in The New Republic, “The Case Against Sotomayor,” which again hammered her supposed intellectual shortcomings. Anonymous quotations from clerks who worked with Sotomayor on the Second Circuit Court of Appeals piled insult on insult. “Not that smart and kind of a bully on the bench,” said one. “She has an inflated opinion of herself, and is domineering during oral arguments but her questions aren’t pen- etrating and don’t get to the heart of the issue,” said another. Rosen’s idea of giving a balanced view was to quote a third clerk as saying, “She’s a fine Second Circuit judge. Maybe not the smartest ever, but how often are Supreme Court nominees the smartest ever?”

The irony was that Tribe and Rosen had both defended affirmative action in the past. It probably did not occur to Professor Tribe when he was defending the Bakke decision in a public debate with Alan Dershowitz in 1977 that the principles he was propounding (“Lower scores and grades need not mean lower ability”) would come back to bite him. He probably believed that for the really important stuff, like Supreme Court nominations, affirmative action would yield to pure meritocracy. Lucky for him, he did not accurately predict what forms of persuasion would work best on Anthony Kennedy.

It annoyed Sotomayor to read these attacks on her competence, especially from anonymous sources and especially from writers on her own political side. She blamed racism: “People kept accusing me of not being smart enough. Now, could someone explain to me, other than that I’m Hispanic, why that would be?” 

If attaining the summit of her profession put Sotomayor in a reflective mood, she might have cast her mind back on the Shaw, Pittman partner thirty years earlier who tried to get her to think through some of the unintended consequences of affirmative action, how it can rebound on its supposed beneficiaries and affect the way they are perceived. This was exactly the kind of thing he was talking about.

From the book BOOMERS by Helen Andrews, to be published on January 12, 2021, by Sentinel, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC. Copyright © 2021 by Helen Andrews. 



Become a Member today for a growing stake in the conservative movement.
Join here!
Join here