Breaking In: The Rise of Sonia Sotomayor

by Joan Biskupic

  And almost immediately after the 2008 election, Souter was ready to give the new Democratic president an opportunity for a Supreme Court appointment.

  Souter loved the law but had disliked Washington, D.C., from the start. Soon after moving to the nation’s capital in the autumn of 1990, the fifty-one-year-old bachelor known for his ascetic life made it clear that he did not want to mix with the town’s elite. He turned down the many invitations for social occasions that came his way and preferred to eat a lunch of apple and yogurt alone at his desk. He longed for the years when he could read Thoreau and the other classics of literature that enthralled him, rather than face mounds of legal briefs piled on the desk in his chambers, where he liked to keep on few lights and work in semidarkness. When the Supreme Court term recessed each summer, Souter took off in his Volkswagen Jetta for his small family farmhouse in New Hampshire.

  As he become a reliable vote for the liberal wing, in 1992 he was critical to the five-justice majority in Planned Parenthood of Southeastern Pennsylvania v. Casey that upheld a woman’s right to abortion. He joined the left on other social policy issues, opposing the death penalty and supporting affirmative action. Souter, who succeeded the liberal Brennan and became his friend, also dissented in a succession of cases in which the conservative majority curtailed the federal government’s authority to enforce civil rights laws against the states. In 2000, when the conservative majority decided the case of Bush v. Gore, cutting off the Florida election recounts and giving Texas governor George W. Bush the White House, Souter was devastated. He believed that the decision, reversing Florida state court action, undermined the integrity of the federal judiciary. He thought the Supreme Court should leave it to the Florida state judges to establish uniform standards for problematic ballots rather than halt the recounts and effectively declare Bush the winner over Vice President Al Gore. He felt betrayed by his conservative colleagues in the majority.

  Souter told friends he might retire after the 2004 presidential election, no matter who won, but when George W. Bush defeated U.S. senator John Kerry and earned another four-year term, Souter decided to stay. By 2008 it was well known at the Supreme Court that Justice Souter was hanging on for a Democrat to win back the presidency.

  In the November 8, 2008, election, Democratic senator Obama of Illinois beat Republican senator John McCain of Arizona to become the first African American to take the White House. Obama overwhelmingly won the black vote—96 percent—yet also won the largest share of white voters of any Democrat in a two-man race since 1976, as well as a wide margin of the Hispanic vote. Hispanics had voted for Obama over McCain by a ratio of more than two to one, 67 percent versus 31 percent, according to an analysis by the Pew Research Center’s Hispanic Trends Project. All told, 9 percent of the 2008 electorate was Hispanic.4

  Obama, the son of a white mother from Kansas and a black father who had grown up in Kenya, prided himself on transcending America’s enduring racial divisions. He also understood and appreciated that he could make history in another important way—by putting a Hispanic on the Supreme Court.

  When he met with legal advisers in Chicago after his victory, Obama was keenly aware, too, that the Court had only one woman. The nation’s first female justice, Sandra Day O’Connor, had retired in January 2006 to care for her husband.5 Justice Ruth Bader Ginsburg, who had been appointed by President Bill Clinton in 1993, was the sole woman left.

  Ginsburg, the former women’s rights advocate, made sure the nation knew she was there, even if alone. When President Obama addressed a joint session of Congress for the first time in February 2009, Ginsburg was recovering from pancreatic cancer and chemotherapy treatments, but she dragged herself to the evening event and sat with her brethren. She said she wanted to make sure that people watching the nationally televised address saw that the Supreme Court had at least one woman.6 Around the same time, Ginsburg also said in the most emphatic terms that she thought the Court needed another woman—that the presence of a single female justice sent a discouraging message about women’s roles in society. The “worst part,” she remarked, is the image projected to students who visit the Court: “Young people are going to think, ‘Can I really aspire to that kind of post?’”7

  Anyone paying attention to the politics of judicial nominations knew that President Obama would be inclined toward a woman appointee for an opening on the Court and be drawn to the idea of naming the first Hispanic.

  Sonia Sotomayor was paying attention.

  With sharp political instincts, she was also her own best agent. That quality had been apparent since childhood. She occasionally protested that she was simply going with the flow of national events, but her ambition and drive set her apart. As Sotomayor wrote in her autobiography, once she set herself on the path of a legal career, “I saw no reason to stint on ambition.”8

  In early 2009, Sotomayor, at fifty-four, had not lost the urgency of youth. Soon after Obama took the White House, she invited Carlos Ortiz, the former president of the Hispanic National Bar Association, to her Greenwich Village condominium for breakfast. Ortiz had been at the forefront of Hispanic lawyers’ efforts to win Supreme Court representation. She showed him around the apartment that she had redecorated, served hot cocoa and cookies, and then got down to business.9 She wanted advice on how she could be ready for a Supreme Court opening.

  “She happened to volunteer that line about how getting to the Supreme Court is like being struck by lightning, twice,” recalled Ortiz. “She was trying to be humble. She said, ‘If you have advice, I’m happy to hear what you would say.’” Ortiz said he urged her to think about connections she had, who she could tap in the administration, and any potential obstacles she might need to confront. He said she mentioned her diabetes. “She had been afflicted with this since [childhood] and has been really good about keeping it in check. I told her she shouldn’t be as concerned about it.” Like others, he had observed that she never hid the condition or let it slow her down. “She just pulls out her kit,” Ortiz said, referring to the insulin shots she gave herself. “And boom!”10

  For nearly twenty years Ortiz had been working with other Hispanic lawyers to try to persuade a president to name the first Hispanic Supreme Court justice. For years, they had been putting up names. Now, in 2009, Sotomayor, with her Ivy League credentials and seventeen-year tenure on the federal courts, looked like an unstoppable contender, at least to Hispanic groups.

  * * *

  Beyond the Hispanic community, well-connected Sotomayor supporters were already speaking on her behalf to people who would matter. Legal insiders knew that this was important. Groundwork had to be laid. Other possible contenders on Obama’s early list—notably Wood and Kagan—had surrogates reaching out to administration officials and other opinion shapers in the nation’s capital for early support.

  Two colleagues of Sotomayor’s from the Second Circuit appeals court, Judges Guido Calabresi and Barrington Parker, arranged a visit with White House counsel Gregory Craig a few weeks after Obama’s inauguration. Calabresi had long known Sotomayor, a former student of his at Yale Law School, and Parker was an old pal from the federal trial court in New York (they shared a Yankees ticket package).11 Calabresi said that their mission did not arise from an effort to promote Sotomayor; they wanted to draw Craig’s attention to a range of judicial issues important to them. Still, when the topic of the Supreme Court came up, he wanted to set Craig straight on an element of Sotomayor’s reputation. “You’re going to hear how she’s tough in court and she’s aggressive,” Craig recalled Calabresi saying. “But she’s a great judge, and she runs an exciting hearing. It’s nothing out of the ordinary.”

  The former Yale Law School dean, then a fifteen-year veteran of the Second Circuit, said in a later interview that he wanted to demonstrate, preemptively if possible, the sexism at the heart of criticism that Sotomayor was too aggressive during oral arguments. Because of past complaints about her from lawyers, Calabresi said, he had been keeping track of
her questions and those of male judges. If anyone asked, he said, he “was able to give chapter and verse on how this was entirely sexist.” Calabresi found her tough and demanding but not beyond the norm of what lawyers and other spectators should expect from the bench. “She isn’t rude,” he said, “but she goes after you.” He believed that Sotomayor was being criticized for behaving as he and other male judges might.12

  Summing up the conversation with the Second Circuit judges, Craig said, “They were anticipating what was going to come out of the lawyers from the Second Circuit who were pushed around a bit by her.”13 Even before Souter had announced his retirement, Sotomayor allies were trying to counter such comments as those found in the Almanac of the Federal Judiciary, which news reporters and legal analysts often used as a guide: “She abuses lawyers” and “She really lacks judicial temperament.”14 The groundwork laid by Calabresi to counter such statements, along with his willingness later to praise Sotomayor’s intellect and abilities in interviews with reporters, would be crucial to her appointment. Judge Parker said that a few weeks after their meeting he received a call from associate counsel Susan Davies, who worked with Greg Craig, mentioning criticism about Sotomayor’s intellectual caliber. “I told her, what you’ve got to remember is that she won the Pyne Prize and she was summa at Princeton.”15 In the early weeks of Obama’s new administration, Davies and Cassandra Butts, a deputy to Craig, were troubleshooting potential nominees.

  Justice Souter had quietly informed the Obama administration that he would be leaving at the end of the term in late June, and he had asked for advice on the timing of his public announcement. The White House suggested that he wait until June. There were other, more pressing legal dilemmas to address. During the presidential campaign Obama had vowed to close the U.S. naval prison on Guantánamo Bay, where more than two hundred detainees taken into custody from around the world were being held because of suspected links to terrorist activity after the September 11, 2001, attacks. Ending their indefinite detention seemed simple at first. On January 22, 2009, the new commander in chief issued an executive order to close the prison. But each prisoner’s case required careful review before he could be released, prosecuted, or transferred to a foreign nation. Further complicating matters, foreign countries were reluctant to take back their nationals who had been linked even indirectly to terrorism.

  President Obama also faced scores of vacancies on the lower federal courts, and the administration was running into trouble with Senate Republicans over nominees. Obama’s ideological opponents had laid groundwork early. Former Reagan administration attorney general Edwin Meese and other outspoken conservatives wrote a letter to Republican senators in January 2009, two days after the inauguration, predicting that Obama was planning to appoint judges who reflected “the most radical judicial activist philosophy of any president in American history.” Meese, an architect of conservatives’ thirty-year drive for control of the bench, and other like-minded conservatives kept the pressure on by going to see Senate minority leader Mitch McConnell and Senate Republican whip Jon Kyl. Their message: “President Obama’s unprecedented call for judicial activism must be met with an unprecedented level of Senate scrutiny.”16

  That rhetoric did not reflect the reality of Obama’s approach to nominations for the bench. He was seeking racial and gender diversity more than a set ideology. Nonetheless, many Senate Republicans were ready to believe the dire predictions of activism. In the president’s first major nomination, he chose U.S. district court judge David Hamilton for a seat on the U.S. Court of Appeals for the Seventh Circuit, which covered Illinois, Wisconsin, and Indiana. The administration considered Hamilton a moderate choice and a peace offering to conservatives after years of judicial wars. The nephew of former U.S. House member Lee Hamilton, an Indiana Democrat, he had the support of the state’s senior Republican senator, Richard Lugar. Despite his bipartisan bona fides, Judge Hamilton’s nomination was stalled in the Senate for most of 2009. Republicans justified their action by citing a 2005 district court decision in which Hamilton barred the Indiana House of Representatives from holding an opening prayer session that mentioned Jesus Christ as the Messiah. Hamilton said such references were “sectarian in the Christian tradition” and violated the Constitution’s separation of church and state.17

  It became clear that if Hamilton—with his moderate record on the bench, connection to Washington, and support of an influential Republican senator—had confirmation problems, it was likely that Obama’s future nominees were going to run into trouble as well. And they did. The only way Obama was able to win Senate action on his nominees to the powerful D.C. Circuit, in fact, was through Senate Democrats’ change in filibuster rules in 2013, allowing the nominees to get a straight up-or-down vote.

  In the spring of 2009 Justice Souter was content to wait to make his retirement announcement, but his hand was forced during the last week of April. National Public Radio’s Nina Totenberg and NBC TV’s Pete Williams aired stories on April 30 reporting that the justice was expected to retire. The next day, Souter made it official.

  “I just got off the telephone with Justice Souter,” President Obama told reporters in the White House press briefing room that Friday, May 1. “And so I would like to say a few words about his decision to retire from the Supreme Court … Justice Souter … came to the bench with no particular ideology. He never sought to promote a political agenda. And he consistently defied labels and rejected absolutes, focusing instead on just one task—reaching a just result in the case that was before him.”

  Obama then described the qualities he would seek in Souter’s replacement. He said he wanted someone with stellar academic and professional credentials. He also said those credentials needed to be grounded in real-life experience. Specifically, he said, the candidate needed to possess “that quality of empathy, of understanding and identifying with people’s hopes and struggles as an essential ingredient for arriving at just decisions and outcomes.”18 Conservative critics of Obama seized on his aspiration for “empathy,” declaring it an invitation to judicial activism—as if empathy could not coexist with impartiality—and later made it a subtext of their confirmation complaints.

  After Souter’s formal announcement, people who had been quietly making moves behind the scenes on behalf of possible nominees shifted into high gear. They wrote to President Obama. They lobbied top aides. They connected with news commentators and other opinion shapers. In an earlier era, there was value in a surprise nominee, but by the 2000s it seemed that the best strategy was an air of inevitability for a candidate in the media and the corridors of power.

  The administration’s lawyers had already started talking to potential nominees, even though they thought they would have more time before Souter’s retirement was announced. White House counsel Craig, along with Davies and Butts, had begun to reach out to candidates, including Sotomayor, with questions, and they wanted these individuals to start filling out paperwork about their records and finances. Sotomayor said she first heard from Craig on April 27.19 Four days later, when Justice Souter announced he would be retiring, the calls from the White House team increased.

  Meanwhile, Obama’s legal and political advisers pored over candidate files they had gathered independently. The political team was anchored by Rahm Emanuel, Obama’s chief of staff, who had been a policy adviser to President Clinton and served in the U.S. House of Representatives, and David Axelrod, a longtime adviser to Obama. Vice President Joseph Biden, who had experience as a Senate Judiciary Committee chairman, also played a central role in the discussions. Biden brought in two top aides who had worked on the Senate Judiciary Committee and been with him for years: Ronald Klain, his chief of staff, whose Supreme Court nomination experience dated back to the Robert Bork nomination in 1987, and Cynthia Hogan, his chief legal counsel, who had worked for Biden since 1991.

  Top lawyers and political advisers scrutinized Sotomayor as well as Judge Wood in Chicago and Elena Kagan, who that spring had
been confirmed as U.S. solicitor general, overseeing the government’s appeals to the Supreme Court. Other names were added to the short list, including Department of Homeland Security secretary Janet Napolitano and former Michigan governor Jennifer Granholm. Judge Merrick Garland of the U.S. Court of Appeals for the D.C. Circuit was considered, but then his name was set aside as the process went along. Administration insiders wanted a woman nominee, and they also thought that Garland, who had won strong bipartisan support when he was confirmed to the appeals court in 1997, could serve as a compromise choice later if another vacancy opened in an election year and if the Senate at the time was controlled by Republicans.

  In the early weeks of the search, advisers said, Obama leaned toward Judge Wood, who had served on the Seventh Circuit since 1995. She had been a law clerk to Supreme Court justice Harry Blackmun and then worked as an attorney at Covington & Burling, where she focused on antitrust and commercial litigation. She also taught courses at the University of Chicago Law School and wrote law review articles. Wood was a deep thinker who could offer an intellectual counterpoint to the Supreme Court’s conservatives. In an expansive 2004 address at New York University, she argued that “our eighteenth-century Constitution, while a bit cryptic at the edges, is nonetheless a real treasure. Approached the right way, there is every reason to be confident that the dynamic process that has sustained it will continue to do so through the years, decades, and even centuries to come.”20 Such a view clashed with that of the reigning conservative luminary, Justice Antonin Scalia, who believed the Constitution and its amendments should be interpreted in the context of when they were written.