Still, I wasn't willing to prosecute a case that I simply didn't believe in, my zeal as a prosecutor finally circ.u.mscribed by my impulse to always keep both sides in mind. The impulse had first developed in Forensics Club as a matter of strategy, but in this setting it sometimes produced the inescapable awareness that, though I might win, justice would not be served. I was especially lucky, therefore, to have a mentor in John Fried, who embodied just that kind of measured att.i.tude. Under an impossible caseload, his commitment to fairness was fundamental. If I believed in a defendant's innocence or doubted a witness's story, I would knock on John's door. We'd sit down together and a.n.a.lyze the evidence for as long as it took. In the end he might suggest offering a very low plea bargain, but he always left me an out: "If you can't in good conscience try the case, then don't."

John's essential fairness was of a piece with the idealistic standards that Bob Morgenthau set for the DA's Office. Nevertheless, it often felt as if we were swimming upstream against muddy currents with the right answer not clearly in view. With each prosecutor handling around a hundred cases at a time, expediency and rough justice were the order of the day. We fudged, we made do with the tools at hand, we performed triage in the trenches, but we still made an effort to do it with integrity.

MAYBE MY PROSECUTING misdemeanors with a ferocity usually reserved for felonies looked to some like real fire in the belly. In reality, it was still more like b.u.t.terflies and the unremitting fear of leaving anything to chance that made me prepare and argue so intensively. But for whatever reason, I was among the first in our duckling group to be moved up to more serious crimes. By the time I switched to felonies, John Fried had moved up too and was replaced as bureau chief by Warren Murray. Warren had a very different style: extremely soft-spoken but a 100 percent hard-as-nails prosecutor. I worried about how I would fare under him.

I was given a handful of low-level felony cases and a few others that were being retried. One of those cases involved a purse s.n.a.t.c.hing. The defense attorney alerted me that it was flimsy, and I was dismayed to see that the facts were indeed thin to the point of being nonexistent. The young defendant had a clean record. His teachers had described him as quiet, polite, well behaved, but developmentally slow. He'd never missed a day of school. I interviewed the victim, an elderly woman. She hadn't seen the thief's face as he ran up from behind her, heading in the general direction of the subway entrance. The police grabbed a confused kid they found sitting downstairs on the platform bench, waiting for his train home from school. The woman identified him by the dark jacket he was wearing, like that of the thief, though she couldn't say what color it was. The purse was never found.

I wrote up a description of the evidence and took it to Warren. "You're right," he said. "It's weak. But we have the indictment, and it's our job to prosecute. Let the jury do theirs; they'll acquit him." I went back to my desk and pondered how to argue this to a jury. I went home to Princeton that night and thought about it some more. But I could imagine no way of standing up in court and saying with a straight face that there was sufficient evidence to convict.

By the time I marched into Warren's office in the morning, I was full of righteous indignation, fiery but totally in control. "I'm not trying this case. I can't lie to a jury. If you think you can go into that courtroom and argue that this is grounds to convict, then you'll have to do it yourself." I threw the file on his desk and walked out.

He came running after me. "Look, I just needed to make sure that you were sure."

"Why didn't you just ask?"

"Sometimes I figure I have to play devil's advocate."

I could have done without the drama. The office declined to prosecute the case.

THE FIRST TIME I found myself before Judge Harold Rothwax, he was in a full-throttle tantrum over the many delays that had dragged out a case before I'd caught it on rea.s.signment. "And now, obviously," he shouted, "you're going to tell me that you're new and need a month to prepare!" I promised him that if he gave me fifteen minutes to confirm the availability of the witness, I'd be ready for trial the following week. That endeared me to him permanently. With plenty of misdemeanor trials under my belt, I had enough confidence-or the bravado of ignorance-to trust my performance under pressure. If nothing else, I knew my own standards of preparation. And sure enough, I would never once suffer the shame of his sarcastic warnings about "avoiding the dangers of over-preparation" dished out to so many other attorneys. I would, however, one time get a compliment of sorts out of him when, reading one of my motion papers, he allowed, "Misspellings are supposed to be a sign of genius. You must have plenty of it."

Judge Rothwax dealt with all felony pretrial motions for my trial bureau. He was painfully exacting and infamously unforgiving of lawyers who wasted his time, on one occasion sending defense counsel to jail for ten days for preventing the start of a trial. He was known as the Prince of Darkness, Dr. Doom, and Yahweh, among other epithets, particularly for striking terror in the heart of defendants whenever one with a weak case would decline his offer of a plea. His notorious stock line to defense counsel: "Your client has the const.i.tutional right to go to prison for the maximum time allowable."

But it wasn't just fire and brimstone. Behind the infernal humor, a formidable clarity of mind and a keen legal ac.u.men kept the docket moving with astonishing efficiency. A good judge must possess management skills as well as a deep understanding of the law. And there is no overstating the value of being able to keep all the facts of a case in your head. He might spend two minutes at a conference on a routine case, more on especially complicated ones, but two months later he would remember every detail.

However caustic, Judge Rothwax was no cynic, though like many a cynic he had been disillusioned, having started his career as a Legal Aid attorney and civil rights advocate before becoming a prosecutor. That early experience led him to conclude that given all the elaborate protections of the rights of the accused, any defendant whose case eventually came to trial was almost certainly guilty. In a controversial book, the judge proposed abolishing the Miranda warning and other rules that he believed handicapped the police and prosecutors; he also argued that a 102 jury verdict was close enough to unanimous for conviction. I wasn't prepared to accept his presumption of guilt, although it is borne out statistically: policemen don't normally make arrests on sheer caprice; most defendants do turn out to be guilty. But a probability of guilt doesn't seem reason enough to revise our standards of due process. These are designed to protect everyone from the human frailties of those whom we entrust to enforce the state's tremendous powers. Even if the vast majority of the law's agents exercise these powers scrupulously, it is unconscionable that anyone should pay for a crime of which he was unjustly accused. Blackstone's famous ratio ("better that ten guilty persons escape than that one innocent suffer") still speaks to a deep-seated sense of what is just.

Though I differed with some of Judge Rothwax's views of procedure, and didn't have much use for his hammy Prince of Darkness persona, the integrity and rigor of his thinking, his pa.s.sion for the law, and the efficiency of his courtroom won my admiration. And he, in turn, offered me kind encouragement, even inviting Kevin and me to his home. As with Jose Cabranes, the deepest respect could not make me into a good enough protegee to take all his advice. Nevertheless, during those years at the DA's Office, a long-nurtured dream finally found a living example in Harold Rothwax's black-robed presence, the first embodiment of an ideal I would be able to observe up close.

NOT LONG AFTER I moved to felonies, I prosecuted the same defendant in two trials back-to-back. It was two different crimes; hence the two trials: the accused had jumped bail on an older charge of burglary, the outstanding warrant discovered when he was caught for a subsequent robbery. My cases were solid, but matched against a very experienced defense attorney from Legal Aid, I lost them both. It was a hard blow to my ego, but what was even worse, I couldn't figure out where I had gone wrong.

"Okay. Tell me what you did," Warren said in his usual tones, still the quietest voice I've ever strained to hear. I walked him through my presentation of both cases. He identified the problem instantly: I was appealing to logic, not morality, and in effect letting the jury off the hook. Since it is painful to most jurors to vote "guilty" and send a human being to jail, you couldn't simply reason with them to do it; you had to make them feel the necessity. "They have to believe that they have a moral responsibility to convict," Warren said. Even the most perfectly logical argument, absent pa.s.sion, would make the choice seem like one of personal discretion rather than solemn duty.

Communicating your own moral certainty didn't necessarily mean chewing the scenery. But as when I had described the Kitty Genovese murder in forensics compet.i.tion, the difference between winning and losing came down to the appeal by emotion rather than fact alone. It was something Abuelita could have told me without ever having gone to law school. And it was something I apparently knew in high school, if only intuitively, before the awareness was pushed aside by years of learning to reason dispa.s.sionately at Princeton and Yale.

Granting myself permission to use my innate skills of the heart, accepting that emotion was perfectly valid in the art of persuasion, amounted to nothing less than a breakthrough. Warren would teach me much else in the way of trial skills, as had John Fried, Katie Law, and others at the DA's Office. But that was the single most powerful lesson I would learn. It changed my entire approach to jurors, from the voir dire to the structure of my summations, and the results spoke for themselves: I never lost a case again. I had hung juries a couple of times, and once or twice a conviction on fewer than all counts of the indictment, but never an acquittal.

Leveraging emotional intelligence in the courtroom, as in life, depends on being attentive; the key is always to watch and listen. You don't need to take notes with the court reporter getting down every word. Lower your eyes to your pad, and you're bound to miss that hint of a doubt that flits across the witness's face. Scribble instead of listening, and you won't notice the split second of hesitation in which a witness hedges a choice of words, avoiding the ones that would flow naturally in favor of the ones whose truth he or she is more certain of.

Such attentiveness also figures in upholding one of a litigator's paramount responsibilities: not to bore the jury. Again, the key is not rhetorical pyrotechnics. What holds a jury's attention, essentially, is the quality of one's own attention. If you are palpably present in the moment, continuously mindful of and responsive to your listeners, they will follow where you lead. If, however, you are reading from a script, droning on as though they weren't there, soon enough they won't be, irrespective of how una.s.sailable your argument.

Often the difference is a matter of remembering what makes sense to a human being as opposed to another lawyer. For example, a prosecutor usually has no need to prove motive under the law, and yet the human mind naturally constructs its reality in terms of causes and effects, weighing any theory against the plausibility of these links and how they might operate in someone else's mind. "Why would she have done that?" is something we instinctively ask before we allow ourselves to conclude "she did it." The state's case is a narrative: the story of a crime. The defense has only to cast doubts on the coherence of that story. The "why" elements of the story must make sense-what would have motivated this person to hurt that person-before you can engage the jurors' empathy, put them in the shoes of the accused or the victim, as needed: make them feel the cold blade held against their necks, or the pang of unappreciated devotion that might drive someone to steal from a former employer. It is the particulars that make a story real. In examining witnesses, I learned to ask general questions so as to elicit details with powerful sensory a.s.sociations: the colors, the sounds, the smells, that lodge an image in the mind and put the listener in the burning house.

Of course, narratives can be slippery. A story might change midway through the telling or the retelling. It wasn't enough to prepare meticulously, to antic.i.p.ate every contingency, every conceivable counterargument. Katie was the one who taught me what to do when, through no fault of your own, the story unfolding suddenly changes, throwing your case into unexpected chaos. In that eventuality, everything depends on the power to improvise, the dexterity to change tack as if doing so were part of your strategy all along. If a witness alters his testimony without warning, the savvy prosecutor simply de-emphasizes the testimony and stresses the c.u.mulative weight of circ.u.mstantial evidence. Devising the case is always a two-step process: build the strategy out of reason and logic; then throw yourself into it, heart and soul. But if you have to revise the plan, suspend feeling and revert to logic until you can think of something you can sell with pa.s.sion.

Other lessons I would figure out for myself, often contrary to conventional wisdom. Some prosecutors, for instance, would look for legitimate reasons to eliminate black and Hispanic juror candidates in the voir dire, the a.s.sumption being that minorities are biased in favor of defendants. But to me that made sense only if you saw all people of color as potential perpetrators and believed, even more implausibly, that they all saw one another that way, too. It was obvious to me that any black or Latino who held a job, or went to school, or stayed home to care for an elderly parent was likely as law-abiding as anyone in my own family and, if anything, far likelier to be the victim of a crime than to commit one. The notion that such a person would, on the basis of racial or ethnic solidarity, let anyone walk who might pose a danger to the community would have seemed laughable where I came from. And so I packed my juries with the kinds of people I'd grown up among; the results, again, spoke for themselves.

Few aspects of my work in the DA's Office were more rewarding than to see what I had learned in childhood among the Latinos of the Bronx prove to be as relevant to my success as Ivy League schooling was. It was in effect to see that mastery of the law's cold abstractions, which had taken such effort, was actually incomplete without an understanding of how they affected individual lives. Laws in this country, after all, are not handed down from on high but created by society for its own good. The nearer one was, in fact, to the realities that had inspired those laws, the more persuasively one could argue for the justice of upholding them. To be able to relate to jurors as their own sister or daughter might, with real appreciation of their concerns and the constraints upon their lives, often put me at an advantage facing an adversary from a more privileged background-a refreshing change after years of feeling the opposite. But even more important, that connection fed my sense of purpose. Each day I stood before a jury, I felt myself a part of the society I served.

It was, as I've said, not the job that most Yale Law School graduates dreamed of, but it did furnish me with the basis for an eventual judicial temperament in ways that Yale could not. It also gave me the confidence that came of recognizing my personal background as something better than a disadvantage to be overcome.

CHAPTER Twenty-Two

IN THE SPRING of 1980, seven months into my first year at the DA's Office, Bob Morgenthau encouraged me to join the board of an organization he had helped to found and had served for the better part of a decade. "They're on a campaign to recruit young talent, and I have given them your name," he said. In those days, few ADAs gave much time to pro bono work, or had much time to give. I already felt the combination of the daily commute and my caseload was testing my limits, which should have activated my natural tendency to avoid taking on too much too soon. But it's always hard to refuse the boss's invitations, and this was especially true of the Boss, who would become such a patron of my career. Besides, I was no stranger to the organization in question: the Puerto Rican Legal Defense and Education Fund (now Latino Justice). I had applied for a summer internship there while I was at Yale. During the interview, they asked about my career goals. I allowed that I hadn't settled on a short-term plan, but I did know that in twenty years I wanted to be a federal district court judge. The interviewer raised an eyebrow, causing me to conclude that in the future it would be better to keep my fantasies to myself. I didn't get the job, but I remained interested in the group's mission.

The Fund, otherwise known by the acronym PRLDEF ("Pearl-def"), was founded in 1972 by a group of young Puerto Rican lawyers who drew inspiration from the NAACP's Legal Defense and Educational Fund and wanted to use their legal skills to challenge systemic discrimination against the Hispanic community. By the time I joined, PRLDEF was solidly established and had won significant reforms, its landmark ASPIRA suit against New York City's Board of Education proving as vital to Hispanics as Brown v. Board of Education had been to blacks. Until the ASPIRA case, Puerto Rican kids coming from the island, where Spanish was used in public schools, or from families like mine that spoke little English entered the New York City public school system with no help at all making the language transition. These kids routinely floundered and, though otherwise perfectly capable, would often find themselves in cla.s.ses for the intellectually disabled. They naturally dropped out in staggering numbers, turning an imagined handicap into a real one, a temporary need for remedial help into a lifetime of minimal employment and poverty. The ASPIRA consent decree won by PRLDEF in 1974 established the right of students with limited English to receive bilingual education in New York City's public schools. The very next year, my cousin Miriam would enter college, eventually to graduate as one among the first wave of young teachers to earn a degree in bilingual education.

If PRLDEF seemed a natural follow-up to my work at Accion Puertorriquena, this was no ragtag band of student activists but a committed group of highly skilled professionals with far more experience and savvy than I had, their sights set far beyond trying to get one Ivy League college to hire one Hispanic administrator. Some of the victories won by PRLDEF-for voting rights, or against discriminatory hiring practices-would open doors for hundreds or thousands of individuals. These efforts would shift the boundaries of opportunity and civic engagement for people across the nation, far beyond Puerto Rican New York. At the same time, the group was decidedly of my community, and that moved me deeply. It was the same pride I'd felt observing Jose Cabranes, so committed to his people and yet maneuvering so effortlessly in the wider world. On our board sat the Brahmins of Nuyorican society-as well as Puerto Ricans from the island and across the mainland-but there were also figures prominent in mainstream media or businessmen wealthy beyond what I had imagined possible in our corner of society. I was awakening to how much broader the Latino community was than I had known growing up in the Bronx.

As the youngest member of the board-even the others recruited as "young blood" were older and more established professionally-I felt honored just to be included and given the chance to learn from individuals already so accomplished and destined to achieve even more. If I could have looked into the future, I would have seen friends I made there going on to become federal judges, amba.s.sadors, a U.S. attorney, college presidents, professors of law, partners at major law firms-every one of them upholding a lifelong dedication to public service. The women were especially inspiring, and not only for offering one another constant camaraderie and moral support, rare in any organization. At the DA's Office, I had seen very few women in positions of genuine power; the bureau chiefs were all men. But here were women-competent, authoritative, professional Hispanic women-who were leaders in their own fields as well as determined to give of themselves for the sake of others.

I worked on the litigation committee, which hired the staff lawyers and set strategy for the types of cases we would take on. I also served on the education committee, which arranged internships and found mentors for minorities, as well as developing LSAT preparation materials to help more Latinos become law students. Beyond what I was learning from all the potential role models around me, these activities gave me a grounding in the nature of organizations and how competing interests within them had to be balanced: in a word, politics. The staffing work in particular threw me square into the problem of allocating limited resources. There were those with visions of taking on ever bigger cases and more areas of advocacy, my own preference as always being for smaller, more careful steps. Sometimes personalities clashed, especially given the presence of so many lawyers who had succeeded as aggressive litigators in large corporate settings and who were now maneuvering in the close quarters of a small nonprofit where everyone involved had a deep emotional investment. Occasionally, such conflicts can tear the very fabric of an inst.i.tution if they aren't handled wisely, and indeed that almost happened.

Problems at PRLDEF came to a head in a labor strike that split the organization and proved traumatic for every single member of the board and staff. The points of contention were the familiar stuff of labor-management disputes, not salaries so much-because no one signing up to work there could have expected much of one-as benefits, the formulas for calculating hours, and the compensation for extra work. My natural sympathies were with the staff lawyers, being myself employed as one in the DA's Office and never having been a manager anywhere. But as a board member I had a fiduciary obligation to the inst.i.tution, a ponderous word but a real responsibility that I took seriously, appreciating as I did PRLDEF's value to the larger community.

Learning how to balance the needs of individuals with the no-less-real needs of an inst.i.tution was an important lesson. It's fine to be on the side of the little guy, but he too will ultimately suffer if the health and concerns of the greater body he belongs to are neglected. That point would be driven home a year later, when my mother phoned in tears to tell me that she had lost her job. She, along with the entire staff of Prospect Hospital, had been locked out when it closed without warning. The sudden bankruptcy eliminated dozens of jobs, shattered a close-knit family that had shared their workdays for decades, put homes at risk, and destroyed an inst.i.tution that had revitalized an entire neighborhood. Once again, my heart inclined to those who were locked out of their livelihood, but my head was calculating: What concessions, what better choices, might have preserved the inst.i.tution and avoided this sad loss for all sides? Seeing Prospect Hospital disappear, I appreciated all the more the fine balance, the hard reckoning, and the personal sacrifices that ultimately kept PRLDEF intact through difficult times.

PRLDEF WAS my first real experience of pro bono work and the honorable role of a "citizen lawyer." I would continue serving there for twelve years, long after I'd left the DA's Office and right up to becoming a judge. To use my education to help others was so gratifying that despite having no time to call my own, I would get involved with other groups as well over those years. There was, for instance, my work with SONYMA, the State of New York Mortgage Agency, which was establishing a program to make mortgages available to working-cla.s.s families. We prided ourselves then on the strict criteria for qualification and the fact that most of the loans were repaid. Still, it gave me pause to realize that someone with my own mother's earning power, for all her years of hard work and spotless financial history, could not have qualified even in the category designed to capture the lowest-income applicants. It seemed wrong that there was no way to reconcile the standards of secure underwriting, and the imperative of protecting the inst.i.tution, with the good of helping the most marginal but still deserving, including those like my mother who had never defaulted on any obligation and never would.

I particularly welcomed any chance to work on issues such as economic development and education that were crucial to the community in which I was raised. I not only cared deeply about those people but also understood their needs from firsthand experience. As I made my way in the world, however, I was seeing more and more that no group is an island. Even the most cohesive (or the most marginalized) consists of overlapping circles of belonging, just as every individual's ident.i.ty is const.i.tuted of many elements. To do good ultimately meant seeing any particular interests in a larger civic context, a broader sense of community. The specific needs of people like those I grew up with would always tug at my heart, but increasingly the call to serve was beckoning me beyond the confines of where I'd come from.

It was somewhat in that spirit that I joined New York City's Campaign Finance Board. Unlike PRLDEF and SONYMA, the Campaign Finance Board was a relatively new organization, founded in the wake of scandals that shook New York State in the mid-1980s, when certain vast campaign contributions, undoubtedly corrupting but some perfectly legal, were exposed. The need for oversight in the financing of the electoral process was dramatic, not only to guard against graft, but to ensure access for candidates who would be excluded if money alone determined the race. But before the board's creation there were no regulations in place, no model for the disburs.e.m.e.nt of public moneys. New York was the first major American city to inst.i.tute such reforms, the only other example being Tucson.

What appealed to me was the possibility of devising a structural solution to a long-entrenched problem simply by creating an appropriate set of rules. That's as elegant as ethics gets. It was also an exhilarating exercise in the art of crafting compromise between opposing interests, always my first response to political division. The fact that I had always registered independently, without a party affiliation, enhanced my credibility as a dispa.s.sionate mediator. But the board's greatest a.s.set in laying claim to evenhandedness and procedural transparency was its chairman, Father Joseph A. O'Hare. A Jesuit priest and the president of Fordham University, Father O'Hare was a man of such una.s.sailable integrity that fairness seemed a.s.sured, even as his irreverent sense of humor banished every trace of sanctimony. Under his leadership the board exemplified how a government agency could rise above partisanship to work for a general good.

The CFB was my introduction to the city and state political scenes. Many lawyers I met working there would go on to become power brokers whose awareness of me and eventual support would matter to my career in ways that I couldn't yet imagine. I had always thought my career would be devoted to principles that transcended politics, but the fact is there would have been no way to the federal bench except through such political channels. It would matter crucially that I was familiar to people of influence who, though recognizing I did not involve myself in partisan efforts, could see that I was at least an honest broker. The integrity I had cultivated so jealously out of personal pride would be my calling card when the time came. Or so I was later told.

Sometimes, idealistic people are put off the whole business of networking as something tainted by flattery and the pursuit of selfish advantage. But virtue in obscurity is rewarded only in heaven. To succeed in this world, you have to be known to people. Nevertheless, where politics is involved, a.s.sociations and recognition can work both ways. Years after I left PRLDEF, my involvement with the organization would be raised as an issue when I was nominated to the Supreme Court. Critics charged that Latino Justice PRLDEF (as it was known by then) was a radical organization that no acceptable candidate should ever have been a.s.sociated with. To hear PRLDEF's activities so grossly distorted during the Senate hearings, with no regard for the good it had done the Hispanic community and the cause of civil rights generally, was painful to me and to everyone else who had served on the board generously and honorably. But PRLDEF did not cower from the attacks. The entire staff and board, led by Cesar Perales, a founding member who is now New York's secretary of state, worked tirelessly to rebut the charges and muster community support on my behalf, efforts for which I will be eternally grateful.

CHAPTER Twenty-Three

THIS IS DIFFICULT for me," my mother said. "He is like my son, Sonia. I watched him grow up. This is not easy for me."

"Please, Mami. You think it's easy for me?"