Breaking In: The Rise of Sonia Sotomayor Read online

  “Sometimes, idealistic people are put off by the whole business of networking as something tainted by flattery and the pursuit of selfish advantage,” she said as she recounted her years with the Puerto Rican Legal Defense Fund. “But virtue in obscurity is rewarded only in heaven. To succeed in this world, you have to be known to people.”59

  She was proving to have a knack for that.

  FOUR

  Chance and Connections

  Senator Daniel Patrick Moynihan, a former professor and sociologist, had done tours in Washington with four administrations and been in the U.S. Senate since 1977. He was a shrewd operator who usually could get what he wanted. But in the spring of 1991 the tall New York Democrat with an owlish visage and a mop of silver hair had hit a wall with his recommendations to Republican president George H. W. Bush for federal judgeships. Among them was the name of Sonia Sotomayor.

  Moynihan needed leverage, and he was considering blocking Senate action on another judicial candidate—Michael Luttig, a Justice Department lawyer and rising Republican star—until the administration acted on his recommendations.

  Sotomayor represented much of Moynihan’s life’s work. As a scholar of demographics and a leading but often controversial voice on racial and ethnic policy, long before he met her in the early 1990s, he had been studying people like her, focusing on ethnic aspiration and assimilation, most notably in Beyond the Melting Pot. Now, as a senator, he was seeking diverse candidates such as Sotomayor to recommend for the federal trial court in New York.

  Appointments to the federal bench were the president’s to make—with, as the Constitution dictates, “the advice and consent of the Senate.” For openings on the district courts, home-state senators made recommendations to the president, and they were usually accepted. For the next levels up, the U.S. appeals courts and Supreme Court, presidents jealously guarded and controlled nomination choices.

  Soon after Moynihan was elected senator, he sought a more substantive role in the judicial selection process and instituted two new practices for his recommendations for the district court. First, he established a screening committee for nominees.1 If a panel of lawyers handled suggestions from the legal community and interviewed candidates, he believed, he would have stronger nominees to pass on to the president.

  Moynihan also thought that New York’s two senators should have a say in judicial recommendations made to the president, regardless of their political party. Traditionally, only a senator from the party controlling the White House made trial judge suggestions to the president. Moynihan, however, thought neither political party should have a monopoly on judicial appointments.2 Soon after he took office, he developed a plan—distinct to New York—that for every three recommendations he made to Democratic president Jimmy Carter, Moynihan’s Republican colleague, Senator Jacob Javits, would receive one. Moynihan thought the arrangement would serve the state’s two senators in the long run. Recommending someone for the federal bench was no small privilege. District court judges were appointed for life, and they presided over most of the nation’s federal criminal and civil cases.

  Moynihan’s approach to recommendations for New York–based federal judges continued after Jimmy Carter left office and into the administrations of Republicans Ronald Reagan and George H. W. Bush. But now GOP senator Alfonse D’Amato, who had succeeded Javits in 1980, got three picks to every one that Democrat Moynihan made. That flip of the three-to-one ratio reflected the fact that a Republican White House controlled nominations. The Bush White House did not like giving a Democratic senator any say, which was partly why it was stalling on Sonia Sotomayor and the other U.S. district court candidates Moynihan had recommended in 1991.

  Sotomayor’s name had first come to Moynihan in late 1990 from his screening committee. On paper, she looked good: Princeton and Yale degrees, a job as a prosecutor in the office of the legendary Bob Morgenthau, now handling copyright and other intellectual property cases for Pavia & Harcourt. At thirty-six, Sotomayor was young for a judgeship, but that did not bother Moynihan, who had joined the Kennedy administration before his thirty-fifth birthday. Her public service credentials—the Puerto Rican Legal Defense and Education Fund and the New York State Mortgage Agency—also impressed Moynihan.

  During her five years in the district attorney’s office, Sotomayor had developed a reputation as a tough prosecutor, handling all manner of cases, as Morgenthau would say, from turnstile jumping to murder. In her work at the law firm of Pavia & Harcourt she was traveling to Europe to meet with such clients as Fendi and making more money than she had in her life. She was doing so well that she hesitated a bit in the early days of the process. But the federal bench was part of her long-term game plan. And the firm’s managing partner, David Botwinik, was a childhood friend of Judah Gribetz, the chairman of Moynihan’s screening committee. This was a lucky connection for Sotomayor. Gribetz had worked as counsel to New York governor Hugh Carey and as deputy mayor for governmental relations under New York City mayor Abe Beame. Gribetz’s committee had been casting a wide net for applicants who could bring diversity to the bench in order to reflect Moynihan’s policy and political interests. Botwinik told Gribetz he thought Sotomayor would be an ideal candidate.

  Earlier in 1990 Botwinik had brought an application to her office and told her to fill it out. “He took my work away from me for a week and gave me not only my time and my secretary’s time, but the time of a paralegal and even his own secretary, so that together we could fill out those very burdensome application forms,” Sotomayor recalled.3 With Botwinik’s endorsement, the committee recommended her.4

  Then it was time to meet the senator.

  The two were separated by a generation but had plenty in common. The Bronx Latina and the Irish street fighter had scrapped their way up and now appreciated the markers of their elite education and professional status. Moynihan’s hard-drinking father had abandoned the family when he was ten. Moynihan spent part of his childhood in Hell’s Kitchen on New York’s West Side, shined shoes, and worked the docks. He started taking classes at City College of New York while he was a longshoreman, then joined the navy, serving as a gunnery officer at the end of World War II. When he returned home, he attended Tufts University, earning his bachelor’s degree and eventually a Ph.D. in sociology. Moynihan received a Fulbright fellowship and attended the London School of Economics.

  Robert Peck, a longtime Moynihan chief of staff, said that the senator struggled to reconcile his past with the present. “He couldn’t decide whether he was down in the dirt Irish or a dandy,” Peck said. “In a working-class [tavern], he could belly up to the bar. But to be honest, he felt more comfortable sitting in the lounge of the Carlyle Hotel.”5

  Over the years, Moynihan had developed an extravagant, sometimes exasperating, style of rhetoric that was an amalgam of his Celtic roots and his high-toned education. Sotomayor had no such affectation; she never lost her Bronx accent.

  As she and Moynihan talked in his office, the former scholar of American demographics delved into her background and traced her interest in the law. Sotomayor thought she made one of her best pitches.

  Her confidence surprised Moynihan. The man who had lamented in 1970 “that one-third of the black and more of the Puerto Rican population are dependent on welfare,” knew that the Latina in front of him could have been doomed by her background.6 A few bad choices or rotten luck might have set her on a different path. When the interview was over, Moynihan was ready to recommend her for a trial judgeship. And he told her so.

  “He loved being able to put up a Puerto Rican, a girl from the Bronx who went to Yale Law School,” Peck said.7

  * * *

  Moynihan later asked Gribetz, “Judah, where did you find her?”8 She was indeed a find. In 1991, when Sotomayor was first being considered, women made up just 12 percent of the federal bench, and minorities constituted about 10 percent. In the entire state of New York, not one federal judge was Hispanic.9

  With the backing
of Republican senator D’Amato, Moynihan sent three names to the Bush White House in March 1991: Sotomayor, Deborah Batts, and David Trager. Batts, an African American, had earned degrees from Radcliffe College and Harvard Law School. A former assistant U.S. attorney, she was teaching at Fordham University School of Law. Trager, who was white and dean of the Brooklyn Law School, held degrees from Columbia College and Harvard Law School and had been an assistant U.S. attorney.

  Moynihan made sure the news media knew about his recommendations. He believed that more blacks and Hispanics should be in seats of power, and as a political matter, he knew his support for minorities on the bench would soften some lingering criticism of his earlier racial views.

  “He bitterly resented the way he had been accused of racism,” Moynihan biographer Godfrey Hodgson wrote, observing that “demons of race” had pursued Moynihan throughout his political life.10 Moynihan’s 1965 report to President Johnson documenting the breakup of the black family, along with his earlier Beyond the Melting Pot, could have been interpreted as blaming minorities for their problems. The civil rights community and the liberal establishment were further inflamed by a 1970 Moynihan memorandum to President Richard Nixon that was leaked to the press, in which Moynihan asserted that race relations were being dominated by “hysterics, paranoids and boodlers” on all sides. He advocated a period of “benign neglect.” Civil rights leaders called the memo “a flagrant and shameful political document.”11 Moynihan explained that he was not urging neglect of blacks, but rather a cooling-off period for the angry rhetoric on both sides. “It killed me,” he said years later. “It won’t ever be forgiven; that’s all there is to it.”12

  Still sensitive to such complaints, Moynihan was furious with how The New York Times displayed—or, to his mind, buried—the story about his recommendation of Sotomayor and the others in its March 2, 1991, edition. The news article, with the headline “3 Recommended for U.S. Court; One Is Hispanic,” ran on an inside page in the second section of the newspaper, in what Moynihan regarded as the spot for obituaries.

  The senator fired off a letter to the story’s author, Wayne King. In his abrupt, iconoclastic style, Moynihan declared, “Good God, they hadn’t died! The Obit Page indeed.” Moynihan then struck at the heart of his complaint, if cryptically: “My point is this. These are issues involving social tension at profoundly important levels. Have been writing about them all my life. When the paper correctly decides to report the issues, it unavoidably adds to the tension. Hence a certain proportionality suggests that our story be given a comparable weight.” Moynihan continued, “You don’t have to believe this and won’t, but there is nothing political here. From our point of view. Something much deeper and enduring. Pass it on.”13

  What he considered “deeper” was the nation’s progress on race. He did not view the Puerto Rican Sotomayor and African American Batts as routine candidates by any measure. They were highly credentialed individuals who knew what it was like to be on society’s bottom rungs and face disadvantages because of the color of their skin and their ethnicity.

  Yet Moynihan’s quarrels with the Times were mild compared with his clash with George H. W. Bush’s administration. He blamed some delays, particularly when it came to Batts, on racial politics. He outright told his Senate colleague John Danforth, a moderate Republican from Missouri, that if Justice Department lawyers ended up rejecting Batts, “it is because of the color of her skin. They assume black means liberal.”14

  * * *

  In mid-April 1991 Sotomayor had her first interview with Justice Department aides, including Murray Dickman, an assistant to Attorney General Dick Thornburgh, who was in charge of the department’s judicial screening; Timothy Flanigan, an assistant attorney general who had been a law clerk to former chief justice Warren Burger; and John Roberts, then principal deputy U.S. solicitor general.15

  In the early 1990s John Roberts was a subtler tactician than the aggressive Sotomayor. But neither lacked raw ambition, as would be proven when they ended up together on the High Court more than a decade later. In 2005, Bush’s son, President George W. Bush, would nominate Roberts to be chief justice of the United States. In the early 1990s Roberts’s work in the U.S. Office of the Solicitor General mainly involved crafting legal positions and writing briefs for that office, which represented the federal government before the Supreme Court. But Roberts was a smart political operator whose judgment was sought throughout the administration.

  For her part, Sotomayor quickly learned to work two sides of the nomination process—as a nominee and as a conduit of information. She reported back to the senator’s staff that the Justice Department lawyers had called attention to her age. But she was ready: she had checked recent Republican judicial nominees and their ages, discovering that several had been nominated when they were in their early and mid-thirties. She had faxed a copy of her findings to Moynihan’s office.16

  This was the calculating, hands-on Sotomayor. Unlike many lawyers nominated for judicial office, she was accustomed to pushing overtly for what she wanted. She had long put her career ahead of her personal life, and in these chain-smoking, highly caffeinated days she juggled work at Pavia and Harcourt with monitoring the progress of her nomination.

  A neophyte when it came to the ways of the nation’s capital, Sotomayor nonetheless understood the importance of calling Moynihan’s office regularly. Her sense of urgency would set her apart from other nominees. When a month had passed after her interview and there was no word about progress, Sotomayor checked in again with Moynihan’s staff. The point man was Joseph Gale, a former corporate lawyer who had joined Moynihan’s office in 1985 to work on tax issues. Gale had become a key aide to Moynihan on nominations. He and Sotomayor had been students at Princeton at the same time, although they did not know each other well. After evaluating Sotomayor’s and Deborah Batts’s chances, Gale wrote to Moynihan in May 1991 that the Justice Department appeared “to be sitting on” these two district judge recommendations. He said that department lawyers were not returning his calls. He realized that Moynihan needed some leverage.

  Gale found it with Michael Luttig, then a thirty-six-year-old assistant attorney general. A few weeks earlier President Bush had nominated Luttig for the U.S. Court of Appeals for the Fourth Circuit, based in Richmond. That powerful regional court handled appeals from trial judges in Maryland, Virginia, North Carolina, South Carolina, and West Virginia. The nomination was a plum for Luttig, a former law clerk to Chief Justice Warren Burger and a law clerk to Justice Antonin Scalia when Scalia was a judge on the U.S. Court of Appeals for the District of Columbia Circuit. In 1991 Luttig was overseeing the Office of Legal Counsel, which produced opinions on the president’s constitutional powers. Gale advised Moynihan to put a “hold” on Luttig, thus preventing his nomination from advancing in the Senate.

  Moynihan had seen his recommendations stall before. An earlier choice for a U.S. trial court vacancy in New York had been John Carro. Like Sotomayor, Carro was Puerto Rican, but he was twenty-seven years older and part of the vanguard of the Latino civil rights movement.

  Carro had moved from Puerto Rico to New York with his family in 1937, when he was ten years old. He grew up in East Harlem and attended Benjamin Franklin High School, also Moynihan’s alma mater. Carro went to Fordham University and Brooklyn Law School, served in the administration of Mayor Robert Wagner, and in 1968, after Carro had returned to private practice, Mayor John Lindsay named him to the New York Criminal Court. At that time Carro was one of only a few local Puerto Rican judges, and the first from the Bronx. In 1979 he became a justice in the city appellate division.

  Not only was Carro well-known in New York legal circles, he also had a strong reputation for liberalism and Latino advocacy. He openly lamented the fact that some Hispanic lawyers lost “their identity and commitment” as they moved up in the profession. “I have seen it time and time again where students profess to want to become lawyers to represent their people and right their wrongs,
only to come out of law school and seek a safe job in government or in the corporate world, seldom to be seen in their communities again,” Carro said in the text of a 1980 speech that Senator Moynihan had saved.17

  Carro was one of the early leaders of Latino advocacy. Vilma Martínez, president of the Mexican American Legal Defense and Educational Fund, was another. If the president or times had been different, Carro or Martínez might have been in the running for “first Hispanic” at the Supreme Court two decades before it happened.18

  But in early 1991 Carro asked Moynihan to withdraw his name for a federal judgeship. “As you know it has been almost three years since you first proposed my name to the president,” Carro wrote to Moynihan in January 1991, referring to the fact that his name had been raised first in the administration of Ronald Reagan: “Since that time I have been interviewed several times by the Justice Department and the FBI has done what I can only assume to be a thorough background check. Still, the President has not sent my name on to the Senate … I can only assume that the President’s failure to do so is because he disagrees with the views I have expressed.”19

  Moynihan also was ready to move on. “It is intolerable the way the Justice Department has fiddled with this matter,” he wrote to Carro. “It is our loss, of course … I do not in the least blame you, considering that you must be caught up with mounds of important and interesting cases. We Benjamin Franklin graduates are not getting any younger, and perhaps do well to stay at our posts.”20

  Now, in late spring 1991, Moynihan did not want a repeat of the Carro episode. He agreed with senior aide Joe Gale that temporarily blocking the nomination of Michael Luttig could help Sotomayor and Batts. Gale called Jeff Peck, staff director on the Senate Judiciary Committee, chaired by Joseph Biden, a Democrat from Delaware, and asked that no action be taken on Luttig’s nomination.21