Breaking In: The Rise of Sonia Sotomayor

by Joan Biskupic

  Kagan, a former Harvard Law School dean, had the scholarly academic credentials, too. She was also a power player, having served in the Clinton White House as an associate counsel and policy adviser. At Harvard, she earned a reputation for easing tensions among faculty and bringing in more conservatives. She had no record as a jurist, so observers were not sure whether she had the liberal vigor of Wood. As a new U.S. solicitor general in the spring of 2009, Kagan had yet to argue a case before the Court. Then age forty-nine, she was also the youngest of the three leading candidates.

  Sotomayor lacked the scholarly reputation of Kagan and Wood, but she had graduated from two of the most intellectually rigorous schools in the country. Sotomayor had a long, relatively uncontroversial judicial record; the Ricci decision stood out. She had served seven years as a trial judge and eleven years as an appellate judge. She did not have the direct personal link to the president that Wood and Kagan had, but she had other connections that proved helpful—her Second Circuit judicial colleagues, Manhattan district attorney Robert Morgenthau, and advocacy groups that had long been pushing for the first Hispanic justice. The Hispanic Congressional Caucus, chaired by Democratic U.S. representative Nydia Velázquez, was persuading African Americans in Congress to throw their support behind Sotomayor. Velázquez, a Puerto Rican who grew up in the Bronx, lobbied for the promise that if a black candidate did not make Obama’s short list, the Congressional Black Caucus would back Sotomayor.

  For Obama, ethnicity cut both ways. He understood the value of diversity, but as the man who had not asserted his own racial identity in his campaign, he did not want to be seen as choosing someone simply because of her color and ethnic heritage. He wanted someone he could say had a superior intellect and judicial demeanor. Almost immediately, critics of Sotomayor were raising doubts.

  Three days after Justice Souter’s retirement announcement on May 1, Harvard law professor Laurence Tribe, for whom Obama was a research assistant at Harvard, wrote to the president, recommending Kagan and criticizing Sotomayor. A leading constitutional scholar with a national following, particularly in liberal circles, Tribe first urged the president to use the Souter vacancy as an “opportunity to lay the groundwork for a series of appointments that will gradually move the Court in a pragmatically progressive direction.” Tribe, the author of several casebooks, then dissected the impact of individual justices, saying,

  Neither Steve Breyer nor Ruth Ginsburg has much of a purchase on Tony Kennedy’s mind. David Souter did, and it will take a similarly precise intellect, wielded by someone with a similarly deep appreciation of history and a similarly broad command of legal doctrine, to prevent Kennedy from drifting in a direction that is both formalistic and right-leaning on matters of equal protection and personal liberty.

  If you were to appoint someone like Sonia Sotomayor, whose personal history and demographic appeal you don’t need me to underscore, I am concerned that the impact within the Court would be negative in these respects. Bluntly put, she’s not nearly as smart as she seems to think she is, and her reputation for being something of a bully could well make her liberal impulses backfire and simply add to the firepower of the Roberts/Alito/Scalia/Thomas wing of the Court on issues like those involved in the voting rights case argued last week and the Title VII case of the New Haven firefighters argued earlier.”21

  Tribe was referring to two pending challenges to racial policies, Northwest Austin Municipal Utility District No. 1 v. Holder, testing a crucial section of the 1965 Voting Rights Act, and Ricci v. DeStefano.

  Former Harvard Law School dean Kagan was a natural choice, Tribe insisted. He told Obama she offered “a combination of intellectual brilliance and political skill that would make her a ten-strike, if you’ll forgive my reference to bowling.” The letter continued to sing the praises of Kagan compared with other potential nominees, including Wood, in terms of intellectual persuasiveness on the Court. The private correspondence became public in 2010, when National Review conservative commentator Ed Whelan posted a leaked copy online. Tribe responded to questions at the time of that disclosure by saying his reservations were refuted by Sotomayor’s performance during her first term. In 2014, after studying her nearly five-year tenure, Tribe elaborated, “Simply put, I was totally wrong in ever doubting how strong a Supreme Court justice Sonia Sotomayor would be, as I had done when contrasting her with Elena Kagan, whose nomination I favored at the time.”22

  Yet Tribe was not alone in raising concerns about Sotomayor in 2009. On that same May 4, Jeffrey Rosen, a George Washington University law professor and regular columnist for The New Republic, wrote a piece for the magazine’s website entitled “The Case Against Sotomayor.” The article included comments from people Rosen identified as having “worked with her, nearly all of them former law clerks for other judges on the Second Circuit or former federal prosecutors in New York,” most of whom were Democrats. According to Rosen, none of the individuals in this group “raved about [Sotomayor],” and “they expressed questions about her temperament, her judicial craftsmanship, and most of all, her ability to provide an intellectual counterweight to the conservative justices, as well as a clear liberal alternative.”23

  Rosen said the most consistent concern “was that Sotomayor, although an able lawyer, was ‘not that smart and kind of a bully on the bench,’ as one Second Circuit clerk for another judge put it. ‘She has an inflated opinion of herself, and is domineering during oral arguments, but her questions aren’t penetrating and don’t get to the heart of the issue.’” Her legal opinions were equally uninspiring: “Although competent, [Sotomayor’s opinions] are viewed by former prosecutors as not especially clean or tight, and sometimes miss the forest for the trees.”

  Rosen offered a caveat in his public column, saying, “It’s possible that the former clerks and former prosecutors I talked to have an incomplete picture of her abilities.” But Rosen closed by recommending that President Obama tread carefully: “Sotomayor’s detractors aren’t motivated by sour grapes or by ideological disagreement—they’d like the most intellectually powerful and politically effective liberal justice possible. And they think that Sotomayor, although personally and professionally impressive, may not meet that demanding standard.”

  The provocative essay in the influential liberal-leaning magazine drew widespread attention. The public, of course, did not know about the Tribe letter at that point, but inside the White House the tenor of the Rosen criticism reinforced the Harvard law professor’s private note.

  Publicly, Rosen was excoriated. His article triggered hundreds of comments on the New Republic’s website, many of them negative, calling Rosen sexist and racist. Liberal writers, on Salon and The American Prospect, reacted with similar commentary against Rosen.24 His complaints touched a nerve about gender and class differences. Writing on Salon.com, Rebecca Traister called Rosen’s column “a primer on how we talk about ladies when they are up for big (and traditionally male) jobs like being on the Supreme Court.” She said that Rosen offered some “perfectly valid concerns about Sotomayor … including that former prosecutors have complaints about the tightness and quality of her opinions and that she may not present a ‘clear liberal alternative’ to the conservatives on the court. But when good questions about qualifications or politics are mashed together with low-budget aspersions about how brash, bossy and talkative a powerful woman is, it’s hard to take them seriously.”25

  Rosen said later that he was not presuming to offer a “definitive” judgment but rather to encourage full consideration of Sotomayor’s temperament. White House lawyers were making their own assessments. They were reading through her opinions and speeches, looking particularly at the circumstances of her assertion that a “wise Latina” might be a better judge and at her actions in the Ricci v. DeStefano case. They also considered her health, wondering whether her diabetes could limit her ability to serve as an effective justice or lead to a premature retirement.

  Obama officials knew the “wise Lati
na” comment was inflammatory, but they also knew Sotomayor had expressed that view many times without criticism, including in 1994, well before her 1998 confirmation to the court of appeals. If it raised no red flags with detractors then, why should it now? They believed they could say the sentiment was intended mainly to bolster the confidence of Hispanic lawyers. What they did not realize is how much this assertion of Latina wisdom would ultimately win allegiance beyond women and across heritages.

  The New Haven firefighters’ case was an equally delicate matter—the administration did not entirely support Sotomayor’s action there—and the White House was expecting the Roberts Court to reverse the Second Circuit panel’s decision by the time the term closed in late June. But in the end, administration lawyers came to believe that the Supreme Court reversal would be viewed in the public eye as more of a reflection on the conservative Court than on Sotomayor as an individual judge. The rest of her record was routine and generally unremarkable.

  Sotomayor demonstrated that she had been keeping her diabetes under control and had avoided the eye and nerve damage that can accompany the disease. Early in her career she had kept her condition quiet, but after a hypoglycemic episode at a party at her house, she became more open about her needs. With that openness came the practice of giving herself a premeal injection right at the dinner table, no matter who was with her.

  The White House contacted Sotomayor’s physician and did its own research. Administration aides told reporters that “independent experts” had concluded that she could be expected to serve for many years.

  Sotomayor did not mind talking about her health, especially given how public she was with her insulin shots. But the administration’s probing of other aspects of her personal life, particularly related to former fiancé Peter White, made her bristle. Years later, she would complain about the process. “You know, and I don’t mean to be graphic, but one day after I’d been questioned endlessly, for weeks at a time, I was so frustrated by the minutiae of what I was being asked about and said to a friend, ‘I think they already know the color of my underwear.’”

  She believed that the fact that she was a woman, a single woman, played a role in the queries. “There were private questions I was offended by. I was convinced they were not asking those questions of the male applicants … I wondered if they ever asked those questions of the male candidates. But the society has a double standard.”26 Administration lawyers said that at the time, Sotomayor grew angry with their questions, but they defended the queries about past personal relationships, saying the stakes were too high not to pursue all angles and insisting that was the routine for male and female candidates. Supreme Court nominees are also subject to FBI background checks.

  By the end of May, President Obama’s team had narrowed the finalists down to Sotomayor, Wood, Kagan, and Napolitano. Individual interviews were scheduled with the president. Judge Wood met with Obama on May 19, after which he told aides she was “as good as ever.” Much was riding on Sotomayor’s May 21 interview, and she prepared extensively. She polled former law clerks for advice, asking them to think of questions she might be asked. She reviewed transcripts of past nominations to anticipate issues that might be on the president’s mind. She wanted to leave nothing to chance.

  When she arrived at the West Wing, Sotomayor chatted first with White House counsel Craig, who had also gone to Yale Law School but whom she had never met. Before turning to an early career as a corporate lawyer, Craig had been a federal public defender, and they talked about that kind of defense work—which at one point in Sotomayor’s life might have seemed the likelier career path.

  When it was time for her meeting in the Oval Office, Sotomayor said she felt at ease and ready to represent herself to the utmost. She highlighted her regard for precedent and said she thought the way she challenged litigants on the bench was an effective way to probe a case. She said she could recall only one other interview during which she felt she was able to so effectively represent herself and her legal strengths—and that was with Moynihan, nearly two decades earlier, when the senator was interviewing potential district court candidates.

  A graduate of Columbia College and Harvard Law School himself, Obama was also impressed that she had the topflight credentials from Princeton and Yale, from Morgenthau’s office, and from her tenure as an appeals court judge on the Second Circuit. But it was her personal intensity and her continued connections to her community that really struck him. The Bronx Latina had not forgotten her roots. Knowing such struggles well, Obama admired how she had traversed worlds defined by race and ethnicity.

  He kept her in the Oval Office for an hour—a good sign, because Obama had a reputation for winding up conversations quickly if he felt they were not going anywhere. As they parted, Sotomayor told him that no matter what he decided, he had made her “the happiest person” simply by his consideration of her.27

  “Wow, she was great,” Obama told top aides. Some said later that if the interview had not gone so well, Obama might have chosen Diane Wood. Said Craig, “As far as I was concerned, watching him, it was between her and Diane Wood.”

  Michelle Obama favored Sotomayor. The First Lady had attended Princeton University as an undergraduate and—almost a decade after Sotomayor—found refuge in the Third World Center. A lawyer, Michelle Obama believed Sotomayor was fully up to the job of a Supreme Court justice.28

  Vice President Biden interviewed Sotomayor by phone on Sunday, May 24. On Monday, Memorial Day, it all seemed settled. President Obama was ready to elevate Judge Sotomayor. But it took him several hours—nearly the whole day—to call her as he had planned.

  Some Obama advisers started to worry that he was having second thoughts. But it was his way to want to reflect on such a momentous choice.

  Meanwhile, Sotomayor was waiting. And waiting.

  “I had been told all weekend that the president would be making up his mind … sometime on Monday, and I had been sitting in my office from eight o’clock that morning waiting for a phone call,” Sotomayor said, adding that the phone calls she was getting were from family asking whether they should begin making their way to Washington as preliminarily arranged.29

  Time kept passing. It got to be 7:00 p.m., and Sotomayor called the White House. As she later recounted, “‘Well, you’re getting my family to Washington. Have any of you given any thought about how I’m going to get there?’ And they stopped and said, ‘Oh, I guess we should figure that out, shouldn’t we?’ Literally, that was the response. What I was told was that the president had gotten distracted with some important other business that was going on at the time, and that he would call me at about 8:00 p.m.”

  She was advised to get ready for the trip to Washington. So Sotomayor raced home to her apartment in Greenwich Village, pulled out a suitcase, and began packing.

  At 8:10 p.m., her cell phone rang. It was the White House operator. Sotomayor held her cell phone in her right hand. She put her left hand over her chest to calm her beating heart. “And the president got on the phone and said to me, ‘Judge, I would like to announce you as my selection to be the next associate justice of the United States Supreme Court.’ And I said to him—I caught my breath and started to cry and said, ‘Thank you, Mr. President.’” The moment produced a blur of emotions, and she said it took many days, weeks even, to get a sense of herself back.

  At 10:30 a.m. on May 26 she entered with President Obama the grandeur of the White House’s East Room—gold silk drapes with swag valances, cut-glass chandeliers, and a full-length oil portrait of George Washington. “After completing this exhaustive process,” Obama said, “I have decided to nominate an inspiring woman who I believe will make a great justice.” The president highlighted her compelling personal story: “She’s faced down barriers, overcome the odds, lived out the American dream that brought her parents here so long ago,” he said.30

  After thanking all the friends and family who had come to Washington to share her joy, Sotomayor offered a tribute
to her mother: “I stand on the shoulders of countless people, yet there is one extraordinary person who is my life aspiration. That person is my mother, Celina Sotomayor. My mother has devoted her life to my brother and me. And as the president mentioned, she often worked two jobs to help support us after Dad died. I have often said that I am all I am because of her, and I am only half the woman she is.”31

  She made a vow regarding the kind of justice she’d be: “I strive never to forget the real-world consequences of my decisions on individuals, businesses, and government.”

  Sotomayor often spoke of the “suspicion” she continued to face about her qualifications, and that was seen in some responses to her nomination. Dana Milbank, a liberal-leaning Washington Post commentator, wrote, “Some thought Obama would nominate Judge Diane Wood or Solicitor General Elena Kagan—big brains who could serve as a counterweight to the court’s conservative philosophers … In selecting Sotomayor, Obama opted for biography over brains.”32

  Yet the broader public response was enthusiastic, notably from all corners of the Hispanic community. And it was not simply the expected organized advocacy groups lifting their voices. It was people on the streets, from grocery stores and beauty shops to university campuses and law firms. Writing in The Washington Post, reporter Eli Saslow captured the unity: “Sometime soon, Hispanics in the United States will once again subdivide into conservatives and liberals, natives and recent immigrants, Cuban Americans, Puerto Ricans and Mexican Americans … But at least for a few hours … America’s largest ethnic minority seemed largely united in appreciation of a historic benchmark.” He wrote that the collective response of the country’s 45 million Hispanics was: “Finally. One of us.”33