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Authors: Jeffrey Toobin

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Kagan was only an outside shot for the Souter seat as well. She, too, had been a professor at Chicago, where she became acquainted with Obama, and had gone on to service in the Clinton White House and then a successful tenure as dean of Harvard Law School. But it had been only a month since she was confirmed as solicitor general, and she had not yet argued a case for the government in the Supreme Court. Indeed, Kagan had never argued a case in any court throughout her entire career. She might be a strong candidate someday—but for now she came off the list.

The field—the real field—quickly came down to two: Diane Wood and Sonia Sotomayor.

10
WISE LATINA

S
onia Sotomayor could have been genetically engineered to be a Democratic nominee to the United States Supreme Court. She had impeccable credentials: Princeton, then Yale Law School. She had ideal experience: big-city prosecutor, six years as a federal district judge (nominated by George H. W. Bush), and then a decade on the federal appeals court. She had, above all, a great story: raised amid poverty in the Bronx, with juvenile diabetes no less, she would make history as the first Hispanic on the Supreme Court. In light of all this, it looked like political malpractice for Obama
not
to nominate her.

There was only one problem. Barack Obama really liked Diane Wood.

When Wood was shuttling her three young children to music lessons in the late nineties, she already had a very busy life. She was a judge on the Seventh Circuit, a Clinton nominee confirmed in 1995, and she taught part-time at the University of Chicago Law School. Still, she sprang a question on her kids’ violin teacher: “Do you know anyone who could teach me the oboe?” Wood spent the next decade in intensive study of that difficult woodwind. Today she sits in with local orchestras.

There was nothing conventional about Diane Wood. Even in the rarefied realm of law professors and federal judges, she had a rich, full, complicated life. She was born in New Jersey but came of age as a teenager in Texas, and she went to the University of Texas for college and
law school. (This alone was an advantage on a Supreme Court dominated by Harvard and Yale graduates. Wood was also a Protestant; at that point, Stevens was the only Protestant remaining on the Court.) In Wood’s day, there were only a handful of women at the law school in Austin, but Wood flourished. She clerked on the Fifth Circuit for Irving Goldberg—a legendary Texas liberal—and then for Harry Blackmun on the Supreme Court. She speaks French, Russian, and German.

After clerking, Wood went to work in Jimmy Carter’s State Department, where she specialized in international trade and antitrust law. She taught at Georgetown and then Chicago, until Clinton summoned her back to Washington to work in the antitrust division of the Justice Department. He put her on the Seventh Circuit in 1995. Along the way, Woods married three times—“my many husbands,” she referred to them ruefully. After a brief marriage during law school, she was with her second husband for twenty years. Dennis Hutchinson was a fellow professor at Chicago and one of Obama’s few good friends on the faculty. In 2006, Wood wed Robert Sufit, a professor of neurology at Northwestern.

On the Seventh Circuit, Wood achieved a rare accomplishment. She was both an unapologetic liberal and a valued, even beloved, colleague to the outspoken conservatives on the Court, Richard Posner and Frank Easterbrook. In her opinions and copious scholarly work, she mounted a vigorous defense of the living Constitution. In an era when originalism was ascendant and many liberals (especially those with ambitions of serving on the Supreme Court) found it convenient to stay away from the debate, Wood took on the subject with enthusiasm. As she stated in the James Madison Lecture at New York University in 2004, the language of the Constitution “may legitimately be interpreted broadly, in a manner informed by evolving notions of a decent society.” She went on:

First and most important is the idea that we should take seriously the fact that the text of the Constitution tends to reflect broad principles, not specific prescriptions. Neither James Madison, for whom this lecture is named, nor any of the other Framers of the Constitution, were oblivious, careless, or otherwise unaware of the words they chose for the document and its Bill of Rights. The papers they left behind leave no doubt that they hoped to be writing for the ages. There is no more reason to think that they
expected the world to remain static than there is to think that any of us holds a crystal ball. The only way to create a foundational document that could stand the test of time was to build in enough flexibility that later generations would be able to
adapt it to their own needs and uses.

This was a direct challenge to the originalist notion that Madison’s words should be interpreted only as he and his peers understood them. Wood applied this mode of analysis consistently—including on the question of abortion.

It was Wood’s misfortune to have several abortion cases before her during her years on the Seventh Circuit. She voted to strike down so-called partial-birth abortion laws in Illinois and Wisconsin and rejected an informed consent law in Indiana. In all of these cases, her colleagues voted to uphold the laws. Worse yet for her chances
was the case of
National Organization for Women v. Scheidler
, in 2001.

The facts underlying that decision were chilling. During the 1980s, anti-abortion groups affiliated with the Pro-Life Action Network engaged in repeated acts of violence against women’s health clinics around the country. NOW used the federal racketeering law known as RICO to sue the group for damages and for an injunction to stop further attacks, and a jury found that the Pro-Life Action Network orchestrated 121 crimes involving acts or threats of violence. As NOW summarized some of the evidence, protesters at a clinic in Los Angeles beat a postoperative ovarian surgery patient over the head with their anti-abortion sign, knocking her unconscious and opening the sutures in her abdomen. In Atlanta, they seized a clinic administrator by the throat, choking and bruising her. They trashed a clinic in Pensacola and assaulted a staff member. The trial revealed a nationwide wave of terror. Wood’s opinion upheld the jury verdict, the damage award, and the injunction against the group.

The Supreme Court reversed Wood’s holding by a vote of 8–1. (Only Stevens dissented.) The reason was narrow. Indeed, the
Scheidler
case demonstrated how cases involving terrible injustices can turn into bloodless disputes about legal technicalities in the Supreme Court.
The justices held that the protesters did not “obtain” any of the clinics’ equipment, so that meant their activity did not fit the definition of extortion under the racketeering law. The case went back to Wood and the Seventh Circuit, which again ruled for NOW, and for a second time in the same case, the justices overturned Wood’s ruling, this time unanimously. (Alito did not participate.) It was true that these cases, as they arrived at the Supreme Court, concerned fairly arcane matters of federal statutory interpretation, not abortion law per se. But it was also true that Supreme Court confirmation fights did not concern such subtleties. In crude terms, the Supreme Court had twice reversed Wood’s rulings on abortion—and even Ruth Bader Ginsburg did not support her position.

To which Greg Craig said, “Good for Wood! This is why we need someone like her on the Supreme Court.” Wood was both a fighter and a thinker, and she could be the voice of their side against Scalia. As a veteran appellate judge, Wood would hit the ground running.

For neither the first nor the last time during his tenure at the White House, Craig was out of step with his colleagues. More importantly, Craig misread his boss. Obama wanted someone who could put together winning coalitions at the Court—more than he wanted someone who could write a good dissent. Obama liked and admired Wood, but the benefits of appointing her were, from a political perspective, unclear. Not so for Wood’s leading competitor. The closer Obama looked at Sonia Sotomayor, the better—in every respect—she seemed.

In the brusque shorthand of political life, White House officials later described Sotomayor’s story as “an American story.” It was an extraordinary one.

Celina Báez and Juan Sotomayor were both born in Puerto Rico and came to the United States as part of the great migration that transformed New York during and after World War II. Celina worked as a telephone operator at a hospital, Juan as a tool-and-die maker in a factory. Their daughter, Sonia, was born in 1954, and they moved into an unfinished Bronxdale housing project in the South Bronx with the poetic name of Building 28. (Her brother, Juan, was born three years later.) Their lives were hard and soon got even harder. When Sonia was
eight, she was diagnosed with type 1 diabetes. The following year, Juan Sotomayor Sr. died
suddenly of a heart attack at the age of forty-two.

Celina was a striver, committed to bettering herself and making sure that her children could do the same. After her husband’s death, she started speaking English at home; as a consequence, Sonia speaks Spanish fluently but her younger brother barely speaks it at all. Celina obtained a GED and then trained to become a practical nurse. The job paid better, and it taught Celina to manage her daughter’s illness. She placed Sonia and Juan in highly regarded Catholic schools. The reasons were educational, not religious. In an oft-told tale, Celina invested in an expensive set of encyclopedias—supposedly the only one in the building—for her two children. The neighborhood was deteriorating, and Celina moved her family to Co-op City, the sprawling development near the Westchester border. While keeping her job at the hospital, caring for her own kids, and serving as a kind of unofficial doctor for her neighbors, Celina commenced studies to be a registered nurse. (The exodus of middle-class families like the Sotomayors in the seventies helped turn the South Bronx into a national symbol of urban decay.)

Sonia won a scholarship to Princeton, where she experienced immediate culture shock. After a rocky freshman year, she settled in and became successful, socially and academically. She wrote a thesis about Puerto Rico’s independence movement, graduated summa cum laude, and won acceptance to Yale Law School. (Her younger brother became a physician.) For all her achievements, Sotomayor held no illusions about one of the reasons for her success. As she said in a speech after she became a judge, “I am a product of affirmative action. I am the perfect affirmative action baby. My test scores were not comparable to that of my colleagues at Princeton or Yale, but not so far off the
mark that I wasn’t able to succeed at those institutions.” In any case, she thrived at Yale, too.

Toward the end of law school, Sotomayor happened to show up at a career-day presentation by Robert Morgenthau, the legendary Manhattan district attorney. After sizing her up, Morgenthau arranged for a job interview the next day, and she was quickly hired. Sotomayor worked her way up in the office and capped her career there with a victory in the tabloid-ready Tarzan Murderer case. Richard Maddicks was a familiar New York type in the seventies and eighties—the desperate junkie who preyed on his neighbors to support his habit. What distinguished
Maddicks was his ability to jump from building to building while making his rounds, a circuit that produced seven shootings and four murders. In 1983, thanks to Sotomayor and a fellow prosecutor, Maddicks was convicted and received a life sentence.

Sotomayor tired of the never-ending misery in the criminal justice system and left the office after only five years to join a small private firm. (After graduating from Princeton, she had married her college boyfriend, whom she had known since high school; he was in graduate school in molecular biology for much of the marriage, and their commuting relationship didn’t last. They divorced after seven years. She was later engaged, but did not marry again.) Like many other young lawyers, Sotomayor was guided both by altruism and by ambition. In 1980, she joined the Puerto Rican Legal Defense and Education Fund—a leading civil rights organization. While in private practice, Sotomayor was named to the State of New York Mortgage Agency board; the next year, thanks to Morgenthau, she gained a seat on the New York City Campaign Finance Board. In 1986,
she toured Israel with a group of Latino activists. When George H. W. Bush was president, the New York senators divided the judicial appointments so that Al D’Amato received three appointments for every one for Daniel Patrick Moynihan. In 1992, Moynihan heard about Sotomayor and put up her name; at the age of thirty-eight, she was confirmed unanimously for a federal judgeship in lower Manhattan.

As with the Tarzan Murderer, a celebrated case brought Sotomayor wide public notice on the district court. A labor dispute had destroyed the 1994 major league baseball season, including the World Series, and the 1995 season was in jeopardy when the battle between the players and the owners wound up in her courtroom. On March 30, 1995, the union demanded that the owners continue free-agent negotiations and salary arbitrations while the two sides negotiated an agreement. Sotomayor told the lawyers that she didn’t know the history of their case, but “I hope none of you assumed … that my lack of knowledge of any of the intimate details of your dispute meant I was not a baseball fan. You can’t grow up in the South Bronx without knowing about baseball.” She issued an injunction reinstituting free agency, the players went back to work, and the 232-day dispute soon ended. It was a classic Sotomayor moment—decisive and unequivocal. It was the kind of behavior that generally wins praise for male judges, if not always for their female
counterparts. Certainly, it did not hurt that Sotomayor became famous as the judge who saved baseball.

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