A judge on the U.S. Court of Appeals for the Second Circuit, Sonia Sotomayor's biography is so compelling that many view her as the presumptive front-runner for Obama's first Supreme Court appointment. She grew up in the South Bronx, the daughter of Puerto Rican parents. Her father, a manual laborer who never attended high school, died a year after she was diagnosed with diabetes at the age of eight. She was raised by her mother, a nurse, and went to Princeton and then Yale Law School. She worked as a New York assistant district attorney and commercial litigator before Senator Daniel Patrick Moynihan recommended her as a district court nominee to the first President Bush. She would be the first Hispanic Supreme Court justice, if you don't count Benjamin Cardozo. (She went to Catholic schools and would also be the sixth Catholic justice on the current Supreme Court if she is, in fact, Catholic, which isn't clear from her official biography.) And she has powerful supporters: Last month, the two senators from New York wrote to President Obama in a burst of demographic enthusiasm, urging him to appoint Sotomayor or Ken Salazar.
Sotomayor's former clerks sing her praises as a demanding but thoughtful boss whose personal experiences have given her a commitment to legal fairness. "She is a rule-bound pragmatist—very geared toward determining what the right answer is and what the law dictates, but her general approach is, unsurprisingly, influenced by her unique background," says one former clerk. "She grew up in a situation of disadvantage, and was able, by virtue of the system operating in such a fair way, to accomplish what she did. I think she sees the law as an instrument that can accomplish the same thing for other people, a system that, if administered fairly, can give everyone the fair break they deserve, regardless of who they are."
Her former clerks report that because Sotomayor is divorced and has no children, her clerks become like her extended family—working late with her, visiting her apartment once a month for card games (where she remembers their favorite drinks), and taking a field trip together to the premier of a Harry Potter movie.
But despite the praise from some of her former clerks, and warm words from some of her Second Circuit colleagues, there are also many reservations about Sotomayor. Over the past few weeks, I've been talking to a range of people who have worked with her, nearly all of them former law clerks for other judges on the Second Circuit or former federal prosecutors in New York. Most are Democrats and all of them want President Obama to appoint a judicial star of the highest intellectual caliber who has the potential to change the direction of the court. Nearly all of them acknowledged that Sotomayor is a presumptive front-runner, but nearly none of them raved about her. They expressed questions about her temperament, her judicial craftsmanship, and most of all, her ability to provide an intellectual counterweight to the conservative justices, as well as a clear liberal alternative.
The most consistent concern was that Sotomayor, although an able lawyer, was "not that smart and kind of a bully on the bench," as one former Second Circuit clerk for another judge put it. "She has an inflated opinion of herself, and is domineering during oral arguments, but her questions aren't penetrating and don't get to the heart of the issue." (During one argument, an elderly judicial colleague is said to have leaned over and said, "Will you please stop talking and let them talk?") Second Circuit judge Jose Cabranes, who would later become her colleague, put this point more charitably in a 1995 interview with The New York Times: "She is not intimidated or overwhelmed by the eminence or power or prestige of any party, or indeed of the media."
Her opinions, although competent, are viewed by former prosecutors as not especially clean or tight, and sometimes miss the forest for the trees. It's customary, for examples, for Second Circuit judges to circulate their draft opinions to invite a robust exchange of views. Sotomayor, several former clerks complained, rankled her colleagues by sending long memos that didn't distinguish between substantive and trivial points, with petty editing suggestions—fixing typos and the like—rather than focusing on the core analytical issues.
Some former clerks and prosecutors expressed concerns about her command of technical legal details: In 2001, for example, a conservative colleague, Ralph Winter, included an unusual footnote in a case suggesting that an earlier opinion by Sotomayor might have inadvertently misstated the law in a way that misled litigants. The most controversial case in which Sotomayor participated is Ricci v. DeStefano, the explosive case involving affirmative action in the New Haven fire department, which is now being reviewed by the Supreme Court. A panel including Sotomayor ruled against the firefighters in a perfunctory unpublished opinion. This provoked Judge Cabranes, a fellow Clinton appointee, to object to the panel's opinion that contained "no reference whatsoever to the constitutional issues at the core of this case." (The extent of Sotomayor's involvement in the opinion itself is not publicly known.)
Not all the former clerks for other judges I talked to were skeptical about Sotomayor. "I know the word on the street is that she's not the brainiest of people, but I didn't have that experience," said one former clerk for another judge. "She's an incredibly impressive person, she's not shy or apologetic about who she is, and that's great." This supporter praised Sotomayor for not being a wilting violet. "She commands attention, she's clearly in charge, she speaks her mind, she's funny, she's voluble, and she has ownership over the role in a very positive way," she said. "She's a fine Second Circuit judge—maybe not the smartest ever, but how often are Supreme Court nominees the smartest ever?"
I haven't read enough of Sotomayor's opinions to have a confident sense of them, nor have I talked to enough of Sotomayor's detractors and supporters, to get a fully balanced picture of her strengths. It's possible that the former clerks and former prosecutors I talked to have an incomplete picture of her abilities. But they're not motivated by sour grapes or by ideological disagreement—they'd like the most intellectually powerful and politically effective liberal justice possible. And they think that Sotomayor, although personally and professionally impressive, may not meet that demanding standard. Given the stakes, the president should obviously satisfy himself that he has a complete picture before taking a gamble.
Jeffrey Rosen is the legal affairs editor at The New Republic