Breaking In: The Rise of Sonia Sotomayor

by Joan Biskupic

  Estrada went into the session irritated, however, because PRLDEF had laid out its cards with a disparaging letter to Senate Judiciary Committee chairman Patrick Leahy, a Democrat from Vermont, before the group’s leaders had talked to him. Written just about a month after President Bush had nominated Estrada, the letter raised concerns about “the nominee’s ultra-conservative views.” Without citing specifics, the June 11, 2001, letter, signed by Figueroa, said, “If the views attributed to Mr. Estrada are accurate, they would place his views well outside the mainstream of American political and legal thought.” The group said it was also disturbed that Estrada “appears to have had no involvement or participation whatsoever in the Hispanic community” and asserted that he “may not have the compassion, open-mindedness, sensitivity, courtesy, patience and freedom from bias … to be an effective jurist on any court.”5

  The meeting in his office, which Estrada said lasted more than three hours, did not allay those concerns.

  Things grew tense when the visitors expressed a series of views that, according to Estrada, boiled down to: “‘You, Mr. Estrada, were nominated solely because you are Hispanic; that makes it fair game for us to look into whether you are really Hispanic. We, having been involved in Hispanic Bar activities for lo these many years, are in a position to learn that you are not sufficiently Hispanic.’ To which my response was—and I felt that very strongly—to point out that the comments were offensive, and deeply so, and boneheaded.”6

  Boneheaded? Ortiz drew back. He had been warned that Estrada could be dismissive and insensitive to the concerns of the Hispanic community. Now he and the others felt they were seeing those qualities firsthand. “Based largely on our personal observations,” the Puerto Rican advocates would later write in a public assessment, “we now firmly believe that Mr. Estrada lacks the maturity and temperament that a candidate for high judicial office should possess.”7

  Estrada was offended. He believed he was being held to a different standard simply because he was Honduran. In his mind, he was as qualified as any high-performing lawyer, regardless of race or ethnicity. He felt he was being squeezed into a mold of what a Latino nominee should be and tested according to criteria he believed were irrelevant to judicial office.

  But there was no escaping the bitter history between the two political parties over lifetime appointments to the bench. To Democrats, Estrada represented an assault on liberalism. Since Ronald Reagan’s presidency in the 1980s, Republicans had used the courts to promote their agenda of conservatism and smaller government. They stacked the bench with jurists who thought that such social problems as overcrowded prisons, environmental disasters, and lingering school segregation should be the province of elected legislators, not appointed judges. Perhaps most significantly, they wanted to curtail the right to abortion embodied in the 1973 Roe v. Wade decision that protected women who sought to end a pregnancy.

  As Barack Obama, then a Democratic senator from Illinois, wrote, “Gaining control of the courts generally and the Supreme Court in particular had become the holy grail for a generation of conservative activists—and not just, they insisted, because they viewed the courts as the last bastion of pro-abortion, pro-affirmative-action, pro-homosexual, pro-criminal, pro-regulation, anti-religious liberal elitism.”8

  When he was running for president against Vice President Al Gore, George W. Bush had said he wanted to appoint justices in the mold of Justices Antonin Scalia and Clarence Thomas. Bush had also strongly suggested that he wanted to name the first Hispanic justice, which meant getting someone positioned, possibly on an important lower court such as the D.C. Circuit, for the moment when a vacancy on the Supreme Court occurred.

  Bush won the election in 2000 with an assist from the Supreme Court in the dispute over the decisive Florida election results. The Supreme Court’s ruling in Bush v. Gore cut off recounts of Florida’s ballots. Despite the saga that stretched from the November 7 election day until the December 12 ruling, Bush arrived in office with a plan for the federal bench, particularly the U.S. appeals courts, and quickly put forward an impressive slate of nominees that included Estrada.

  The D.C. Circuit, to which he was nominated, was aptly dubbed the nation’s second-highest bench. It handled challenges to federal regulations and passed judgment on policies covering such matters as the environment, campaign finance, and workplace safety. The stakes for any nominee to that court were high, especially because so many of its judges moved on to the Supreme Court. In 2001, three of the nine sitting justices were from that bench: Antonin Scalia, Clarence Thomas, and Ruth Bader Ginsburg.

  * * *

  Bush’s selection of Estrada was part of his own grander plan for the federal courts, first unveiled in an East Room ceremony on May 9, 2001. With more White House flourish and invited media attention than ever before for a set of appeals court candidates, President Bush introduced Estrada and ten other nominees: eight men and three women; eight whites, two blacks, one Latino. Estrada stood smiling, his hands clasped in front of him. The carefully orchestrated unveiling included the nominees’ families and other supporters, as well as Attorney General John Ashcroft and Senate Judiciary Committee leaders Orrin Hatch, a Republican from Utah, and Patrick Leahy, the Democrat from Vermont. News reporters were handed three-ring binders with the nominees’ biographies and supporting testimonials.

  Among conservative luminaries nominated along with Estrada were former Reagan and first Bush administration lawyer John Roberts, also nominated to the D.C. Circuit; University of Utah law professor Michael McConnell, for the Denver-based Tenth Circuit; and Ohio solicitor general Jeffrey Sutton, for the Cincinnati-based Sixth Circuit. Like Estrada, they all were former Supreme Court law clerks and leading conservative thinkers, screened and recommended by members of the Federalist Society, a group that had helped scour the nation for conservatives for the courts since the early 1980s. Estrada and Roberts also had been part of George Bush’s legal team during the disputed Florida election battle in December 2000.

  Roberts had the deepest history in GOP administrations, having helped screen judicial candidates during the Reagan and George H. W. Bush years, including when Senator Moynihan was trying to win Sotomayor a U.S. district court seat. The first President Bush had tried to place Roberts, a native of Buffalo who grew up in Indiana, the son of a steel-plant executive and a homemaker, on the D.C. Circuit a decade earlier. At the time, Hispanic activists were pushing for more representation on prominent courts. A White House “talking points” memo in Roberts’s file with the first Bush administration addressed why a Hispanic had not been chosen in early 1992. The memo defended the Roberts decision by calling him “a superstar” candidate and asserting that “the President does not need to nominate a Hispanic to this seat to demonstrate commitment to reaching out to Hispanics.”9

  Senate Democrats blocked Roberts’s nomination back then. They believed that the Reagan protégé who rose quickly in the first Bush administration was a conservative ideologue. Some Democratic committee staffers took an “anyone but Roberts” attitude at the time, and Senate Judiciary Committee chairman Joseph Biden refused to schedule a hearing on his nomination. When President Bush lost to Bill Clinton in November 1992, Roberts went into private practice and began adding commercial clients and pro bono work to his résumé. From his base at the firm of Hogan & Hartson, Roberts became a preeminent Supreme Court lawyer.

  President George W. Bush’s interest in Estrada, also a leading Supreme Court lawyer, stemmed in part from the administration’s attention to an increasingly powerful constituency. Hispanics had become 12.5 percent of the U.S. population, some 35.3 million of the total 281.4 million residents, according to the 2000 census. Mexicans represented 7.3 percent of the total U.S. population, Puerto Ricans 1.2 percent, and Cubans 0.4 percent. Overall, the Hispanic population had increased by 57.9 percent since 1990, up from 22.4 million.10

  Such numbers fueled the expectation that whoever won the presidency in 2000 would want to have a Hisp
anic poised for appointment to the High Court. Both Texas governor Bush and Vice President Al Gore had suggested as much. At this point, the forty-six-year-old Sotomayor, a two-year veteran of an appeals court, was being mentioned in news stories about possible Supreme Court changes if Democrat Gore won the presidency.

  Shortly after Bush defeated Gore and took office, it appeared that the most likely Hispanic candidate would be White House counsel Alberto Gonzales, a Mexican American who grew up in Texas and graduated from Harvard Law School. As governor, Bush had appointed Gonzales to the Texas Supreme Court and brought him to Washington as White House counsel in 2001. But it quickly became evident that many conservatives in the nation’s capital did not trust Gonzales, who took a moderate approach to such Republican agenda items as abortion rights and affirmative action.

  Estrada emerged as a Supreme Court contender in the view of many Republicans and the news reporters following Bush’s deliberations. When Bush nominated Estrada to the federal appeals court in Washington, D.C., the president highlighted his Honduran roots, noting that he was the first Hispanic ever offered a spot on the D.C. Circuit. To counter Estrada’s reputation as a conservative, the White House recruited high-profile Democrats to support him, including Walter Dellinger and Seth Waxman, former top officials in the Clinton solicitor general’s office. Administration officials also obtained a letter of endorsement from Ronald Klain, a Harvard Law School classmate of Estrada’s and a political operative whose Democratic credentials were unquestioned. Klain had been chief of staff and counsel to Vice President Gore and was a close adviser to him during the 2000 election, including as chief counsel overseeing the Florida recounts.

  When Bush officials enlisted him to help with Estrada in 2001, Klain was in private practice in the Washington office of O’Melveny & Myers. But as he endorsed Estrada, Klain reinforced the reality that nomination politics was as much about the past as the present. He noted that earlier Democratic nominees, including Elena Kagan during the Clinton administration, had run into roadblocks and been denied seats on the D.C. Circuit.11 “I think it is unfortunate that this vacancy exists at all due to the Senate’s failure to confirm” prior nominees, Klain wrote. He then said he believed Estrada would be an independent thinker, not a reflexive conservative.12

  Klain’s fellow Democrats were not convinced. The Estrada opposition had come out early and was working in plain sight. In an opinion piece published in The New York Times just six weeks after President Bush announced his first batch of nominees, Senator Charles Schumer of New York wrote, “The not-so-dirty little secret of the Senate is that we do consider ideology, but privately … If the President uses ideology in deciding whom to nominate to the bench, the Senate, as part of its responsibility to advise and consent, should do the same in deciding whom to confirm. Pretending that ideology doesn’t matter—or, even worse, doesn’t exist—is exactly the opposite of what the Senate should do.”13

  The liberal Alliance for Justice had contacted Democratic senators, including Senate Judiciary Committee chairman Leahy, with concerns about Estrada’s conservatism, specifically on civil rights issues. The group also began working with Senators Schumer and Dick Durbin, Democrats who represented key Hispanic constituencies in New York City and Chicago, respectively, to block the Estrada nomination. Alliance for Justice staff met regularly with Senate aides to strategize about how to raise suspicions regarding Estrada in the press and among moderate senators. As one Democratic staffer on the Senate Judiciary Committee told columnist Jack Newfield for a piece in the liberal Nation magazine, “Estrada is 40, and if he makes it to the circuit, then he will be Bush’s first Supreme Court nominee. He could be on the Supreme Court for thirty years and do a lot of damage. We have to stop him now.”14

  Meanwhile, Puerto Rican, Mexican American, and other liberal-leaning Hispanic groups were trying to persuade Chairman Leahy to move slowly on Estrada’s nomination.15 The Puerto Rican Legal Defense and Education Fund, whose lawyers had visited Estrada in the spring of 2002, was one of the first to issue a full report on the nominee. “Of greatest concern to the Latino community is Mr. Estrada’s clear lack of any connection whatsoever to the issues, needs, and concerns of the organized Hispanic community,” the Puerto Rican organization asserted in the September 2002 report. “It is indeed ironic that someone promoted as a Hispanic has neither shown any demonstrated interest in, nor has had any involvement with, any Hispanic organizations or activities throughout his entire life in the United States.”16 The Mexican American Legal Defense and Educational Fund and the California La Raza Lawyers Association submitted a letter and report to the Judiciary Committee, concluding that they could not be sure Estrada would be fair to Hispanics trying to vindicate their rights in the courts.17

  Estrada never tried to portray himself as a standard-bearer for Latinos, as White House officials such as Alberto Gonzales and Republican senators such as Senator Orrin Hatch had done on his behalf. Nor did he try to make himself out to be poor or disadvantaged. “I have never known what it is to be poor, and I am very thankful to my parents for that,” he said.18

  But in the atmosphere surrounding the nomination, his background was an issue. His opponents did not believe he shared or could understand the lives of many Hispanics. “Being Hispanic for us means much more than having a surname,” U.S. representative Robert Menendez, a Democrat from New Jersey, told The Washington Post as he criticized Estrada for being disconnected from Hispanics.19 Around this time, Sotomayor was complaining in speeches that minority candidates for the federal bench often stalled and that no Hispanic had ever been appointed to the D.C. Circuit. But her concern related to Democratic nominees. When she addressed the judicial bickering as Estrada’s nomination was pending, she did not mention him.

  Estrada’s hearing before the Senate Judiciary Committee, just like the meeting with the Puerto Rican advocates, failed to boost his chances of confirmation. On September 26, 2002, the day after he celebrated his forty-first birthday, Estrada sat alone at a long table draped with a green cloth. Behind him were his mother, his sister, and his wife. In this venue, Estrada was not belligerent or especially defiant, but he did not answer senators’ questions to their satisfaction. He also tripped up regarding his screening of young attorneys who sought clerkships with Justice Kennedy, his former boss at the Supreme Court. The issue was whether Estrada had tried to eliminate liberal applicants, a notion he initially resisted and then conceded he may have done.

  Even though he was not as combative as he had been in other settings, his day of testimony was tense and stressful. At several points during the session, his wife, Laury, wiped her eyes. Dressed in a dark suit, white shirt, and red striped tie, Estrada said he was “exceptionally proud of every piece of legal work” he had undertaken.

  Senator Schumer, who was chairing the Judiciary Committee hearing, reminded everyone about an earlier racially charged nomination and warned that he and others had not forgotten what happened. “Clarence Thomas came before this distinguished committee and basically said he had no views on many important constitutional issues of the day … But the minute Justice Thomas got to the Court, he was doctrinaire,” Schumer asserted. “Whether you agreed with him or not, he obviously had deeply held views that he shielded from the committee. It wasn’t a confirmation conversion. It was a confirmation subversion. And there is still a lot of simmering blood up here about that.”

  Some White House officials had thought that in the early 2000s Estrada’s ethnicity would neutralize criticism about his conservatism the way Thomas’s race deflected such issues in 1991. But they were wrong. The aftershocks of the Thomas confirmation hurt Estrada.

  Schumer insisted that he was not questioning Estrada’s legal abilities, but rather his ideology and whether he would be fair. Peering over brown-rimmed reading glasses at Estrada, Schumer referred to Estrada critics, including Arizona State University law professor Paul Bender, who had been Estrada’s supervisor in the U.S. Office of the Solicitor General. B
ender, who did not testify before the committee, had claimed in news reports cited by senators that Estrada lacked judgment and was “too much of an ideologue to be an appeals court judge.”20

  Schumer asserted that because of such criticism, the solicitor general’s office should release memos Estrada wrote about cases when he served as an assistant from 1992 to 1997. “Everyone I have spoken with believes such memoranda will be useful in assessing how you approach the law,” Schumer said, noting that the SG’s office determines the government’s position on important constitutional questions.

  But in fact not everyone thought the memos should be turned over. Seven former U.S. solicitors general, including Democrats Seth Waxman, Walter Dellinger, and Drew Days, had written to Senate Judiciary Committee chairman Leahy to stress the need for confidentiality in the solicitor general’s office correspondence.21

  Estrada told Schumer he did not want to press the Bush administration to release the memos; he did not want his personal interests to eclipse regard for the institutional interests of the SG’s office. Under separate questioning by a number of senators, including California Democrat Dianne Feinstein, Estrada refused to give his view of past cases or to say how he would have voted. He stressed that he was committed to the process of judging, not necessarily the end result.

  The most awkward moments came when senators asked him about a story in The Nation that said that Estrada had screened out liberals who were seeking clerkships with Justice Kennedy.22 Estrada denied the reports that he told candidates they were too liberal for a job in the chambers of Kennedy, a conservative who often swung toward the liberal side in key cases such as the death penalty and punishments for juveniles. Estrada said that if he did say such a thing, it would have been only as a joke.