Breaking In: The Rise of Sonia Sotomayor

by Joan Biskupic

  This time around, she was as poised for battle as the Democratic White House and the Republican-controlled Senate. Her political instincts were sharp, her list of contacts long. She also had a team of loyal boosters, led by Xavier Romeu, a Puerto Rican native who had worked for her as a law clerk in her early years as a district court judge. Sotomayor and Romeu had become friends and had stayed in close contact as she continued to serve as a trial court judge and Romeu moved on to other positions, including executive director of the Puerto Rico Federal Affairs Administration.

  Romeu, who was also vice president of the Puerto Rican Bar Association, became the kind of shrewd and tireless backer that Marty Ginsburg was for his wife, Ruth, and that Senator Kennedy and his aides had been for Breyer. Romeu served as Sotomayor’s troubleshooter, working with her supporters and criticizing her opponents. Even though she had a fat Rolodex with a network of connections, Sotomayor was still a judge, and she still had to act like one. Romeu could press her case in a way that she could not.

  Romeu secured an endorsement from Puerto Rico governor Pedro Rosselló and persuaded him to commit, as Sotomayor later said, “all of his office’s resources to my confirmation.”44 Within a few weeks of her nomination, Romeu visited the White House to talk to top Latino aides in the administration. He kept in close touch with the lawyers handling nominations. He helped organize constituents to write letters to senators. He obtained testimonials from several Latino legal groups, which urged a speedy Senate Judiciary Committee hearing for Sotomayor. He prepared fact sheets listing her strengths and quickly circulated information to counter any criticism emerging in the Senate or from such outside opponents as conservative talk-show host Rush Limbaugh, who was branding Sotomayor a liberal activist.45

  When the Senate Judiciary Committee held its hearing in September 1997, the session was rockier than what Sotomayor had experienced when she was being considered for the district court in 1992. Republican senators focused on her criticism of federal sentencing rules that many judges thought too rigid and harsh. She said that despite her personal feelings, she “imposed what the law required.”46

  GOP senators also brought up a 1992 New York Times story in which she had been asked whether she had sat on her hands when Justice Clarence Thomas addressed a conference she attended. She said in response to the reporter’s question, “I’ll take the Fifth.”47

  “Did you see fit to stand and applaud?” Alabama senator Jeff Sessions asked Sotomayor.

  “He was my Supreme Court Justice of my circuit,” she answered, backing away from the suggestion in the New York Times report. “I stood up.”48

  The Senate Judiciary Committee recommended her to the full Senate in March 1998, but the nomination stalled in the Republican-controlled chamber. There were rumors that Justice John Paul Stevens, then seventy-eight, might retire. Republican senators, including majority leader Trent Lott, worried that Sotomayor would be in line for the Stevens position if she were confirmed to the appeals court.

  So even though she had yet to make it onto the Hispanic National Bar Association’s list of possible Supreme Court candidates, she was very much on the Republicans’ radar screen. GOP partisans, who had been astutely playing judicial selection politics since the Reagan years, understood that Sotomayor could be an unstoppable Supreme Court candidate. They thought that if this rare Latina jurist were confirmed, Republicans would not be able to stop the president from making history by appointing her to the Supreme Court. Mississippi senator Lott understood and refused to allow a floor vote.

  Talk radio host Limbaugh stoked Republican concerns about where she could go from there by saying she was on a “rocket ship” to the Supreme Court. The Wall Street Journal also editorialized against her, citing a similar view that Clinton was laying the groundwork for her eventual elevation to the High Court. “We’d like to think the Republicans may be having second thoughts about Judge Sotomayor and are deliberately delaying her confirmation until seeing whether Justice Stevens announces his retirement when the current Court term ends this month,” the editorial in early June 1998 said.49

  The Wall Street Journal referred to several Sotomayor trial court decisions that it considered antibusiness. In one, Sotomayor had ruled that a law school graduate with learning disabilities was entitled to accommodation under the Americans with Disabilities Act while taking the New York State bar exam. The Journal wrote in its editorial, “By now New Yorkers are accustomed to this sort of antic judicial thinking. But why impose it on the whole country?” Romeu dissected that Wall Street Journal editorial and circulated a fact sheet responding to the criticism, writing that the would-be lawyer “suffers from a neurological impairment that prevents her from automatically recognizing words, thereby requiring her to read and reread sentences in order to decode their meaning.” He pointed out that Sotomayor’s decision had been affirmed by the U.S. Court of Appeals for the Second Circuit.50

  There was no split among Hispanics, as there had been four years earlier over a Cabranes nomination. A diverse coalition of Hispanic groups backed Sotomayor.

  Yet in the end it would not be action by the Clinton White House, Democratic senators, or even Latino advocates that propelled Sotomayor’s nomination forward. It would be Republican senator Alfonse D’Amato who engineered the crucial Senate vote. This occurred a little more than a month before the 1998 November election, when D’Amato faced Democratic challenger U.S. representative Charles E. Schumer of New York.

  D’Amato was trailing among Hispanic voters in the state. Sotomayor’s supporters convinced him that if he went to Senate majority leader Lott and secured a floor vote for her, Hispanics would be more inclined to vote for him over Schumer. So D’Amato pressured Lott to schedule the vote. On October 2, 1998, the Senate approved Sotomayor’s elevation to the Second Circuit appeals court by a vote of 67–29. All the votes against her were cast by Republicans.

  A few weeks later, at her investiture at the Manhattan courthouse, it was clear that Sotomayor had kept up with her networking even after she put on the black robe of a trial court judge. She thanked a multitude of women’s groups and Hispanic organizations. “Hispanic leaders from across party, partisan, and island status lines not only endorsed my nomination and confirmation but also exerted their influence publicly and privately to make this confirmation happen,” she said.51

  She referred to D’Amato’s crucial role and the many people who talked him into intervening, including U.S. representatives José Serrano and Nydia Velázquez and various local Bronx officials. “State Senator Efrain Gonzalez of the 31st District in the Bronx, a man of his word and action, even withheld his endorsement of Senator D’Amato until the senator got me a Senate vote,” she said. (D’Amato lost to Schumer, failing to garner support from several important constituencies, including women, Jews, and Hispanics, but he harbored no hard feelings toward Sotomayor, and in 2009 he urged his former colleagues to support her Supreme Court confirmation.)

  Sotomayor’s vast personal networks also were on display at the appeals court swearing-in. Cousins from Puerto Rico made the trip to New York, as did a Fendi lawyer from Italy whom Sotomayor had known when she represented the luxury-goods maker at Pavia & Harcourt. High school friends attended. Her dentist was there, and Sotomayor observed—as if it were as natural as could be—that she had gotten to know her dentist’s husband and become godmother to one of their children. She praised her mother and, when she referred to her father, said that he died at forty-two in part from the heart complications that had kept him out of the army during the war.

  In one of the most personal moments of the investiture, before hundreds of supporters, Sotomayor addressed her then fiancé, Peter White, a New York construction contractor: “Peter, you have made me a whole person, filling not just the voids of emptiness that existed before you, but making me a better, a more loving and a more generous person … Many of my closest friends forget just how emotionally withdrawn I was before I met you.”

  But she and
White did not marry. The relationship ended early in her tenure on the Second Circuit.52

  Another man who had been a constant in her adult life, José Cabranes, addressed the crowd. “This is a wonderful day in New York…,” he said. “I have been accorded the honor of speaking to you on this happy occasion because, in a professional sense, I was ‘present at the creation.’”

  Much had changed since Cabranes and Sotomayor first met in 1976. She had connected with such other powerful people as Senator Moynihan and had earned the loyalty of men and women in the trenches such as Xavier Romeu. She understood the political milieu of judicial nominations and knew that many forces needed to align for any one individual to reach her goal.

  “There’s no question that between 1992 and 1994 Cabranes was the most talked about, most prominently talked about Hispanic candidate,” recalled Carlos Ortiz, the Hispanic National Bar Association official who worked for Hispanic appointments to the bench. “[Sotomayor] was an avid reader of all this. She learned to make the right connections. There is no question about that. She knew who to be in contact with, who to tell about her interests. I don’t want to say she was campaigning for the court of appeals, but she let people know.”53

  SIX

  The Right Hispanic

  Washington lawyer Miguel Estrada bristled at what he was hearing from the three attorneys who had come down from New York to his office one spring day in 2002 to talk about his nomination to an important federal appeals court. Officials from a Puerto Rican advocacy group, they had already made their criticism known, one going so far as to say in a letter to senators that Estrada might lack the compassion and open-mindedness to be a good judge. And now they were suggesting that any Hispanic nominated to the upper echelons of the federal judiciary should have strong ties to the community—and be proud of those connections. The Honduran-born Estrada, who had graduated from Harvard Law School, earned a prestigious clerkship at the Supreme Court, and was now specializing in appellate advocacy, believed that candidates for elite judgeships should stand on their legal credentials and their character. He thought an emphasis on his heritage conjured up the worst kind of “identity politics” and the presumption that his views would be determined by his ethnic heritage.

  The differences between Estrada and his visitors would hurt his chances for appointment as judge. Other factors were in play as well, including Estrada’s strong conservatism. As President George W. Bush tried to position Estrada for possible appointment as the first Hispanic Supreme Court justice, he became a pawn in the nasty partisan competition over the federal judiciary. What developed would link the fates of Miguel Estrada and Sonia Sotomayor, situated so differently in the eyes of organized Hispanic advocates. Their experiences would reveal what effects prominent Hispanic groups were having in the nation’s capital and what happens when a nominee is opposed or, alternatively, championed.

  * * *

  About a year after Estrada had first been nominated to the U.S. Court of Appeals for the District of Columbia Circuit, he found himself looking across his desk at the three men from the Puerto Rican Legal Defense and Education Fund.1 Spread out before him were newspaper articles about his nomination. Estrada had made special note of the criticism, some of it from the lawyers who now sat in his Washington, D.C., office.

  The three visitors, Carlos Ortiz, Juan Figueroa, and Benito Romano, were Latinos who had made it to the top of the legal profession, just as Estrada had.2 For Estrada and Ortiz, particularly, the meeting marked a significant moment in their respective efforts related to the judiciary. Estrada, forty, had been nominated by Bush to be a judge on the powerful Washington, D.C., appeals court, which was regarded as a springboard to the Supreme Court. Ortiz, forty-seven, held a job in the top ranks of an international food distributor and was chairman of the board of PRLDEF and a past president of the Hispanic National Bar Association. Ortiz had been working for a decade to persuade administrations in Washington to appoint a Hispanic Supreme Court justice. He had taken it personally when Judge José Cabranes was spurned in 1994 for the top court and had cultivated relations with other Hispanics—including Sotomayor—who might be in a position to be nominated for the next vacancy. Sotomayor had been on PRLDEF’s board before becoming a judge.

  Estrada and Ortiz were each highly respected and had wide circles of admirers in the law. Both men exuded polish and professionalism in their demeanor, down to their starched white shirts and pressed dark suits. And at this moment, each man resented what the other was saying. Their competing views related to Hispanic connections and credentials would represent two sides of a debate over who might be in the best position to be nominated as the first Hispanic for the Supreme Court.

  Estrada was subjected to far more scrutiny than the typical nominee for the D.C. Circuit because his supporters—and opponents—recognized that President George W. Bush could be positioning him for the High Court. His nomination led to a record seven filibusters in the Senate and exposed ethnic stereotyping and infighting among organizations that had not been seen since the conflict over Judge José Cabranes during the Clinton administration. Slate columnist Dahlia Lithwick wrote, “As the debate grows uglier, it’s now becoming a contest among Mexicans, Cubans, and Hondurans about who—to paraphrase Snow White—is the most Hispanic of them all.”3

  Estrada’s nomination also reflected the lingering bad feelings among Democrats over the Clarence Thomas confirmation. Democrats recalled how Thomas had been appointed to the D.C. Circuit not long before his 1991 elevation to the Supreme Court—made possible in part because Southern Democrats who might have opposed him were worried about a racial backlash. Critics of Estrada did not want him to be similarly positioned for elevation from the D.C. Circuit. Because of the nation’s growing Hispanic population, the possibility of a first Hispanic justice was even more in the political atmosphere than it had been during the Clinton administration a decade earlier.

  Estrada’s father, a lawyer, and his mother, an accountant, divorced when he was young, and he eventually moved to the United States to be with his mother, who worked as a bank examiner in New York. He was seventeen when he arrived, knowing little English, but he caught up quickly and graduated with honors from Columbia College and Harvard Law School. After his clerkship for Justice Anthony Kennedy at the Supreme Court, Estrada became a federal prosecutor in Manhattan and then worked in the U.S. Office of the Solicitor General, which represents the federal government before the Supreme Court. In public service and now at the private law firm Gibson, Dunn & Crutcher, Estrada had racked up fifteen oral arguments before the Supreme Court.

  This was a special achievement, for Estrada had a stutter that he had to overcome every time he stepped up to the lectern to argue before the justices, and he sometimes struggled to get out the first word of a sentence. The embodiment of intelligence and determination, he also was a conservative, drawing early opposition not only from Latino groups but also from liberal advocates who had begun to mobilize against him even before President Bush formally nominated him. If he made it to the Supreme Court, they speculated, he would undercut progressive gains on abortion rights, affirmative action, and death penalty appeals.

  Another dynamic shaped the debate. Estrada, smart and smart-alecky, was known for saying exactly what he thought, sometimes to the point of offense. In many other parts of the professional world, a contrary or combative personality might not matter. But during a high-stakes judicial nomination, amid the egos of the Senate, a nominee bore the burden of showing deference and respect. Estrada’s regard—or lack of it—for some Democratic leaders would exacerbate his difficulties during the confirmation process.

  Carlos Ortiz was born in the Bronx and grew up in Harlem. He attended the City University of New York, became an accountant, and then went to Brooklyn Law School. He became general counsel at a food manufacturer and rose in the leadership of Puerto Rican and Hispanic legal groups that wanted more Hispanic representation on the nation’s courts. Ortiz had made the appoin
tment of the “first Hispanic” justice a personal mission. He insisted that it did not matter whether the first was a Democratic or Republican appointee, although most of the activists pressing for the appointment were in the liberal rather than the conservative camp.

  Since the George H. W. Bush administration in the early 1990s, Ortiz and fellow Hispanic advocates had been meeting with presidents and their top aides to promote this cause. It had been at a 2001 session with President George W. Bush’s White House counsel Alberto Gonzales that Ortiz first heard Miguel Estrada’s name as a possible Supreme Court candidate. Ortiz had visited Gonzales soon after Bush assumed the White House to press again for a Hispanic justice. Gonzales mentioned that Estrada could soon be on deck for such an appointment.

  Now, in the April 2002 meeting in Estrada’s law firm office, the nominee and his critics from the Puerto Rican Legal Defense and Education Fund, including president Juan Figueroa, thought they might find common ground. The Puerto Rican leaders feared that Estrada was too conservative and out of touch with the Hispanic community. Yet there was no reason, at this point, to think the nominee would be in serious trouble or blocked in the Senate. Estrada had accepted their request for a meeting partly because he knew the third man in the group, Benito Romano. Estrada and Romano had both served as prosecutors in the U.S. attorney’s office in Manhattan. Romano, who had led the office’s anticorruption unit and then temporarily held the top U.S. attorney post, was now on PRLDEF’s executive committee. Estrada would later say he was “delighted” to set up the meeting: “I think of myself as a fair-minded person, who is very concerned that there is anybody out there who may think that I am biased or that I have any character trait that would make me less of a person.”4