A Steady Rise, Punctuated by Doubts
In Sotomayor, an Insider's Achievements Meet an Outsider's Insecurities

By Amy Goldstein
Washington Post Staff Writer
Sunday, July 12, 2009

Within weeks of arriving in New Haven as a law student in the fall of 1976, Sonia Sotomayor fell in with a few first-year classmates whose ascent to Yale Law School was as improbable as her own: a half-Mohawk from Chicago's South Side who had graduated from high school while sleeping on his social worker's back porch; a Chicano from New Mexico whose parents had driven him to nice neighborhoods to see what big houses looked like; a black kid from Washington who had made it into the Air Force; a Puerto Rican high school dropout from East Harlem who had been sent to a halfway house for setting his girlfriend's car on fire.

For three years, this band of brilliant misfits in the preppy Ivy League would be Sotomayor's closest friends, her apartment their hub to cook elaborate dinners and be, as one of them recalls, "our own little support group." But they would not be her only world at Yale.

When she got to the Connecticut campus, Sotomayor placed a call to the university's general counsel, a first-generation Puerto Rican who had scaled academic and governmental heights. José Cabranes had been told by one of Sotomayor's undergraduate professors to keep an eye out for a talented young woman whose parents had, like him, come from Puerto Rico. He hired her as an intern, asked her to help research a book and opened doors rarely cracked for Yale law students, introducing her to visiting dignitaries and inviting her to small dinners at his fine Colonial home.

By the time she was 22, just married and getting her first taste of the law, Sotomayor already had a hallmark of the woman President Obama has now chosen to join the Supreme Court: She was a striking mixture of uneasy outsider and consummate insider.

The 55-year-old appeals court judge, who is to begin her confirmation hearing tomorrow before the Senate Judiciary Committee, would bring to the court a sensibility shaped by a set of experiences -- and an immense network of people -- far more eclectic than those of most sitting justices.

She is a woman who, in public speeches in recent years, has confessed a sense of insecurity, describing herself as "always looking over my shoulder, wondering if I measure up." Yet she also is a woman who, 17 years ago, stunned the marshals in the ornate federal courthouse in Lower Manhattan, who had never seen anything like the 600 people who showed up -- standing on tables, squeezing onto windowsills, cramming into an overflow room -- to watch her be sworn in as a U.S. district court judge.

Interviews with dozens of friends, teachers, colleagues and relatives suggest that Sotomayor is a more nuanced figure than the basic contours of her now-familiar biography: a Horatio Alger-like tale of transcending the odds facing a girl, diagnosed early with diabetes, who grew up in projects of the South Bronx with her mother after her father died of a heart attack when she was in the fourth grade. She would become the product of two Ivy League schools, the Manhattan district attorney's office and a New York law firm with a ritzy international clientele before she was made a federal trial judge, then elevated to the U.S. Court of Appeals for the 2nd Circuit.

At each phase, people who know her say, Sotomayor benefited from devoted mentors who navigated her firmly onto the next rung. But even as she sought their guidance, she has, at times, been openly hesitant about advancement.

She has worked since her student days to promote opportunities for fellow Latinos and maintains a hectic schedule of teaching and speaking engagements, driven to present herself as a role model. Yet she can, at times, be detached from ideology.

She is steely and exacting, with a capacity for work so prodigious that it has frayed her most serious romantic relationships. Yet she remains, at times, vulnerable and emotional in public.

All along the way, she has been in settings in which her background has set her apart. Decades before Obama nominated her as the Supreme Court's first Latina, Sotomayor was one of a few minority students at a Catholic high school, one of the only Puerto Ricans at Princeton and on through Yale, until she eventually became the first Latina federal judge in New York state. Yet she came along at a time when she could see horizons in Puerto Ricans a bit older, could find that being a Latina offered advantages. As far back as high school, she had an example in Herman Badillo, the Bronx borough president who, in her junior year, became the first Puerto Rican in Congress.

"We were on that cutting edge," said Margarita Rosa, who recruited Sotomayor into a tiny Puerto Rican student group at Princeton and has been a close friend ever since, "where certain things were becoming possible."

At Every Stage, a Mentor

José Cabranes, who is now a judge and colleague of Sotomayor's on the 2nd Circuit, was her most influential early mentor. But he was just part of a chain of people who guided and invested in her at every turn in her life and career -- from the South Bronx to the federal judiciary.

As Sotomayor was growing up in a family in which no one had gone to college, people prodded her to excel.

"The females were expected to achieve more," said her younger brother, Juan Sotomayor. She loved comic books -- Archie, Casper, Richie Rich -- so much that, after her father died, her paternal grandmother and aunts once convened a family meeting with her mother. "They were concerned about the role of the comic books in my sister's life," recalled her brother, an allergist outside Syracuse, N.Y. "It was maybe corrupting her."

Classmates from Cardinal Spellman High School remember Sotomayor as serious and self-assured, and, while most students were bound for college, she aimed for the Ivy League. In a blend of the fearlessness and vulnerability that has been a pattern in her life, she traveled to Cambridge, Mass., for an interview at Harvard, and then came home and announced that she no longer was interested. "She sensed that the woman [admissions officer] was condescending to her," said her friend, Dawn Cardi, a New York lawyer to whom Sotomayor has told the story. "It made her feel she wouldn't be welcome there."

Princeton seemed to Sotomayor a more plausible path because -- as would happen repeatedly for her -- someone already there and willing to help her urged her to apply. In this case, it was an undergraduate from a poor family like hers, who had been a year ahead of her at Spellman and helped coach her for high school debates.

By the fall of 1976, when Sotomayor arrived at Yale Law and called Cabranes, she already had learned to "look for people who are knowledgeable and experienced to see if they can help in her quest to help herself," as her friend Nancy Gray, a Los Angeles lawyer, put it. Cabranes was Yale's main lawyer, but he also was researching a book about Puerto Rico's history and identity. He enlisted Sotomayor and Felix Lopez, her friend who had surmounted his years as an East Harlem juvenile delinquent, believing their heritage "would make them more interested in finding out the mysteries here," Cabranes said. "They represented for me . . . the fulfillment of one's hopes for . . . the sort of people [who] would emerge in a second generation."

Like her mentors before and since, Cabranes saw in Sotomayor intense engagement, competitiveness and a methodical, analytic style. These would be evident when she was plowing through boxes of documents for him in a small office in Yale's international law library. And later, when she was training to cross-examine her first witnesses. And even now, piecing together the jigsaw puzzles she loves and playing poker with a group of New York women, as she does some weekend nights.

Cabranes was responsible for Sotomayor's first job, through circumstances that, once again, involved their common ethnic roots. He had admired Manhattan's legendary district attorney, Robert Morgenthau, from the days when Cabranes was a founder of the Puerto Rican Legal Defense and Education Fund and Morgenthau was an original member of its board. During Sotomayor's final year of law school, Cabranes recommended her to him.

Yale graduates almost never took jobs as state prosecutors, regarding the role as too pedestrian, and Sotomayor had not considered the idea. But Cabranes sensed she would like the trial work -- and would benefit from something more. "Morgenthau had several hundred people who worked for him, but not that many he had . . . discovered," Cabranes said. "It would be highly unusual to have the personal patronage and concern of Morgenthau."

Five years later, when Sotomayor, by now divorced, was eager for broader legal experience and a larger paycheck, Morgenthau picked up the phone and helped her get hired at Pavia & Harcourt, a well-regarded law firm. There, too, she immediately found a mentor in an exceptionally bright partner named David Botwinik, who worked with her intensively, assigning her to cases with high-flying clients in Italy. "She was invited into the homes of these people," recalled her friend Gray, with whom she had worked at the D.A.'s office. "That was huge."

And seven years later, it was Botwinik who would, in turn, call a childhood friend running a committee that New York's longtime Democratic senator, Daniel Patrick Moynihan, had set up to screen possible candidates for federal judgeships.

Her succession of mentors had led her, by age 38, to the federal bench.

Strong Identity, Little Ideology

Since her earliest years, Sotomayor's identity has been inseparable from her ethnicity -- from the sofrito she watched her mother and aunts make on Saturday mornings to the dozen years she spent on the board of the Puerto Rican Legal Defense and Education Fund, now known as LatinoJustice PRLDEF.

But this intense ethnic sensibility has not corresponded with intense ideological views. One example: Voter registration records going back to before Sotomayor became a judge show that she has not belonged to a political party, according to the New York City Board of Elections.

The divide between her strong identity and scant ideology can be glimpsed in the last name she adopted for several years: Sotomayor de Noonan. Weeks before starting law school, she married her high school boyfriend, Kevin Noonan, a handsome young man who would go on to be a biologist and lawyer. Though his family was Irish, she "liked the use of 'de Noonan,' " Cabranes recalled. It was syntax common in Latin America but was, Cabranes noted, "not consistent with the feminist movement. It means 'belonging to.' "

It was not the first time that Sotomayor struck those around her as detached from prevailing ideological debates. Her high school years coincided with the height of the Vietnam War, and even in her Catholic school, the counterculture crept in. Many girls wore peace buttons on their uniforms' navy blazers; Sotomayor did not, friends recalled. And she disapproved when the boys' senior class president organized a boycott of a major school fundraiser as an antiwar protest, according to Joe Antolin, a good friend from that time who was a student government leader. Sotomayor, then president of the girls' junior class, was more concerned with a plan to merge the girls and boys divisions the following year, Antolin said. Instead of protesting, he said, they spent countless hours examining how to meld the constitutions of the two student governments.

Later, when Sotomayor was at Yale, David Rosen, a New Haven lawyer for whom she interned one semester, asked her what she wanted to do professionally. It was a question he asked every intern, but her answer was one he had never heard before -- and hasn't since. She wanted, he said she told him, to be a federal judge.

"What was striking to me was that she was inspired by the ideal of neutrality," Rosen said. "Not that [the law] is an instrument to get somewhere, like a shovel. She was saying, no, I'm not going to be playing for the Hispanic team, the Democratic team, the Republican team. I'm going to be playing for the Constitution team."

'People Are Her Hobby'

Even Sotomayor's closest friends complain that it is hard to see her, that her schedule is booked, often months in advance, with speaking engagements, seminars for law students, work with high-schoolers.

They tell of the controlled chaos that is her chambers, with the judge juggling documents, phone lines, assignments to her clerks, requests to her longtime assistant to make restaurant reservations. She always takes work home.

Such intensity is in part the legacy of her lifelong, self-imposed pressure to prove herself. "When you are the first one through the door, it weighs heavily on you," said Drew Ryce, her law school friend who is half-Mohawk. "You can't be a screw-up."

It is also in part out of her need to be a role model.

"I've tried many times to say, 'Can you slow down a bit? You don't have any time for yourself,' " Cardi said. "And she'll say, 'But I made this commitment.' The community has pinned their hopes on her. It's very hard for her to say no."

And it is in part simply her personality.

"People are her hobby," said her friend Ellen Chapnick, a Columbia Law School dean who co-taught courses with Sotomayor for years.

Examples abound: in the huge holiday party she threw in her chambers -- in a courthouse unaccustomed to them -- less than three months after becoming a judge, making sure to invite janitors and security guards. In the gatherings at her Greenwich Village condominium, where relatives with scant education mingle with legal titans.

Then there was the time in January when Sotomayor invited her friend in Los Angeles, Gray, to join her on a visit to see her mother and stepfather in South Florida. They went to lunch one day at a favorite Cuban bakery in a shopping plaza. While her family and friend sat at a table, munching on their sandwiches, Gray recalled, "Sonia is up chatting with the people behind the counter about their children."

Toughness and Vulnerability

For all her toughness, her savvy and her attainments, Sotomayor can be a vulnerable figure in public.

On Nov. 6, 1998, she was sworn in to the 2nd Circuit before a throng even larger than the 600 who had gathered six years earlier to see her become a trial judge. As the judges, lawyers and friends from all walks of life looked on, Sotomayor ended her remarks with an emotional ode to her fiance at the time, a construction and architectural consultant named Peter White. "[T]he professional success I had achieved before Peter," she told the crowd, "did nothing to bring me genuine personal happiness."

Then she spoke directly to him. He had, she said, filled "the voids of emptiness. . . . You have altered my life so profoundly that many of my closest friends forget just how emotionally withdrawn I was before I met you."

They were together about eight years. In a brief interview, White said: "Unfortunately, she is extremely dedicated to her work, which takes up 90 percent of the time. There wasn't room for two careers in one household."

Her strikingly personal tone in the midst of her swearing-in was one of many ways Sotomayor has exposed her vulnerability. Another is in the way she approaches the disease she has had since childhood. "The diabetes is a metaphor," her friend Chapnick said, for her open nature. "I mean, she shoots up in public," Chapnick said. Unlike most insulin-dependent diabetics, when Sotomayor goes to restaurants, as she does often, she does not retreat to a ladies room to keep her blood sugar in check. She carries a black kit in her purse and, seated right at the table, pricks her finger, reads the test results, raises her shirt and gives herself a shot.

Still another way her vulnerability manifests itself is through occasional reticence that can seem to border on self-doubt. As a law school intern, she said her goal was to be a federal judge, and yet both times the possibility of a judgeship materialized, she hesitated at first.

Before her elevation to the appellate court, she told friends that she worried the work might feel remote and lonely. But her deeper hesitancy came the first time, for the district court judgeship.

David Glasser, a fellow lawyer at Pavia & Harcourt, remembers that when her mentor there, Botwinik, broached the idea, "Sonia said: 'Look, I can't do that. I would never be good at that.' "

Benito Romano, a lawyer who served with Sotomayor on the Puerto Rican Legal Defense and Education Fund's board, remembers late-night phone calls urging her to apply. "My impression was, she was stunned by it. I think it took her awhile to take it in."

In a speech at Hofstra University three years ago, when Sotomayor was awarded an honorary degree, she recounted that her mentor had tried for three months to persuade her to submit her name for consideration. "I told him it was a useless enterprise, they would never pick me," she said. "He took away my work, put an application on my desk and said, 'Fill it out.' "

She did. And then -- once she got the job -- the insider in her took over.

She called on Judge Miriam Cedarbaum, one of the court's few women at the time. Cedarbaum, now a friend, remembers the visit because it was so unusual. The new judge said to the more experienced one that a mutual friend "suggested to me that I should seek you out as my mentor."

Supreme Court Speculation

Late one night four months ago, Margarita Rosa, who had been one of Princeton's few other Puerto Ricans, was in the passenger seat of Sotomayor's Saab convertible when she raised the question. They were heading back to Manhattan from Long Island, where Sotomayor had been driving to a nursing home three evenings a week to visit one of her best friends, Elaine Litwer, who had had a series of strokes and would die a few weeks later. On that night, a new Democratic president was in the White House and, even before Justice David H. Souter announced his retirement, speculation was swirling over who Obama might choose to fill his first Supreme Court vacancy.

"Wow. How does it feel to have your name always appear on the shortlist?" Rosa, who directs a settlement house on the Lower East Side, asked her friend of three decades. Sotomayor did what she always did when Rosa asked. "She never seemed to assume it was a given. She didn't dismiss it either. It was just there."

The buzz was something Sotomayor had been living with for years. It was, said Judge Guido Calabresi, a fellow member of the 2nd Circuit who had taught her torts class back at Yale, the reason her nomination by President Bill Clinton to the appeals court had been held up for 13 months. "Even then, she was thought of as somebody who was a real possibility for the Supreme Court," Calabresi said. Republicans "decided that they wanted a little bit of mud thrown."

Still, Ryce, one of her law school crowd, said it was never "within the rational expectations of this highly rational woman. . . . She would say, 'No, it's not going to happen.' "

The talk, Cardi said, "was an embarrassment sometimes to her."

The day in May 2006 that Hofstra awarded Sotomayor the honorary degree, the university's president, Stuart Rabinowitz, recounted the path of her career. Just before a blue doctoral hood was placed over her head, he paused.

"And someday, perhaps to the Supreme Court," he said, "but I don't know."

Sotomayor smiled a tight-lipped smile and looked down at the stage floor. The outsider in her had trouble taking it in.

Research director Lucy Shackelford and staff researcher Madonna Lebling contributed to this report.

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