In Supreme Court Pick Sotomayor, an Insider's Rise Meets an Outsider's Doubts

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."

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