Courting Controversy

U.S. District Court Judge Nancy Gertner could tell one thing for sure about Alexander Leviner, a black man from Roxbury: He had bad luck in cars. It didn't much matter where he was sitting — driver seat, passenger seat, back seat — because the flashing lights of police cruisers invariably interrupted his travels.

Once the police pulled him over, they usually discovered Leviner was doing something illegal: driving with a suspended license; driving someone else's car without their permission; carrying marijuana; carrying crack cocaine; and, in his most serious offense, carrying a semiautomatic handgun and 14 rounds of ammunition.

It was that transgression that landed the 33-year-old asbestos remover in Gertner's courtroom in 1998. The convoluted formula for sentencing guidelines, based on a defendant's criminal history, required that Gertner send Leviner to prison for between 46 and 57 months. She sentenced him to 30. In justifying her decision, she said Leviner's previous offenses “overstated his culpability and the likelihood of his recidivism.” But she went one step further, arguing that Leviner's rap sheet of mostly minor motor vehicle violations would probably have been significantly shorter had he been white. He was, Gertner reasoned, a victim of that increasingly contentious practice, racial profiling.

Civil rights groups applauded her rationale, believed to be a first of its kind in federal sentencing. It was certainly ahead of its time, preceding as it did the intensifying public debate over racially profiling Arab-Americans and others that would follow this fall's terrorist attacks. But critics chafed that it was just another example of how Gertner, a former civil rights activist and criminal defense and workplace discrimination attorney, had taken her activist instincts to the bench. “I had high hopes that Judge Gertner would leave her activism behind when she became a judge, but she is still on an activist crusade,” says one Boston lawyer. “In criminal cases, she functions as both the 13th juror and lead defense counsel. She bends over backward for defendants, particularly in criminal cases. The sense among some people is that she's totally out of control.”

Ruffling feathers is nothing new for Gertner, who has made a career out of it. As a young attorney, she was an outspoken liberal and feminist who wore bright red dresses in court, carried her legal briefs in shopping bags, kept a file on sexist lawyers and judges called “sexist tidbits,” and outworked and outsmarted just about every male prosecutor she faced. She would become one of the most sought-after attorneys in Boston after winning radical activist Susan Saxe a considerably lighter sentence than expected following Saxe's murder conviction in 1976.

A 1994 Clinton appointee, Gertner has issued mostly mainstream rulings while continuing to incite controversy. Specifically, her decisions in civil rights cases and her willingness to speak her mind — including to the news media — keep her in the spotlight. In an embarrassing slap early this year, the U.S. Court of Appeals for the First Circuit ordered Gertner to remove herself from a racial discrimination case because of comments she made to the Boston Herald about the complexities of it.

In many ways, it's surprising to see the 55-year-old Gertner on the bench at all. Federal judges are usually former prosecutors, often with predictable legal careers, not liberal and outspoken products of the '60s and '70s counterculture movement.

“Frankly, I never thought I could be a judge,” says Gertner. “How was I going to sentence people to jail terms I didn't agree with? How was I going to enforce laws I didn't believe in? So this is the greatest challenge for me. I see the process of judging as a constant struggle to acknowledge where my feelings end and where the role begins.”

Nancy Gertner is sitting on the front porch of her Brookline Victorian in a pleasant, tree-lined neighborhood overrun by polite dogs and adolescent boys on bicycles. It's a lazy Saturday morning, and she's talking about the joys of domestic family life while her husband, ACLU legal director John Reinstein, and their two teenage boys make occasional appearances, pushing bicycles and petting the family dog, Lucy.

Gertner seems almost as surprised about how she went from firebrand lawyer to wife and mother as she is about how she ended up a federal judge. “I never expected to have a family,” she says, sporting jeans, a long-sleeve blue shirt, and flip-flops. “Growing up, my family had been so traditional, and I was completely reacting against that. So my career was in lieu of, not in addition to, a family. I was a workaholic. I still am a workaholic. I'm not very good at acknowledging limits.”

That's a trend that began in high school, where Gertner was valedictorian, a popular member of the cheerleading squad, a staff member at the literary magazine, and runner-up for homecoming queen. “I worked hard; I collected boyfriends; I did everything in excess,” she says. “I couldn't figure out who I was. It's still a problem.”

The one thing she knew for certain was that she loved to argue. She learned to do it in the company of her father, Morris, a linoleum and tile store owner who would stay up until 2 a.m. with his daughter in the family's small apartment in Flushing, New York, debating civil rights laws, sex roles, and Red China's admission to the United Nations. Frustrated and fatigued, Morris would give up. “Oh, go be a lawyer!” he told her.

His daughter wanted to attend Radcliffe, but Morris Gertner didn't want her to leave New York. So she went to Barnard, where freshmen were required to take a course on hygiene. “They would teach you how to get in and out of taxicabs so that no one could look up your skirt,” Gertner recalls. “But we also read The Feminine Mystique. Big mistake. It was eye-opening and earth-shattering in that it provided a vocabulary for my discomfort.”

By her senior year, all Gertner and her friends could talk about was the Vietnam War. Urged by a roommate to start speaking out, Gertner began marching in demonstrations. “It was a life-changing experience,” she says. “My father was appalled.”

Yale Law School followed, but Gertner wasn't sure if she wanted to pursue a career in law or political science. What she did know was that the law school was a hotbed of activism, and she wanted to be a part of it. “It certainly felt like we were changing the world, and that all the old premises were up for grabs,” she says. “Premises about women, race, war, government, country — it was all up for debate. Even the legal doctrine was being challenged. The law school describes it as the Dark Ages.”

At Yale, she met another woman who was hell-bent on a successful career: Hillary Rodham. The two became friends and spent much of their free time, according to Gertner, yelling at each other. “I laugh when I read these articles today talking about Hillary being a radical,” Gertner says. “She was a moderate. She was cautious about her future in a way that I wasn't. I just didn't have the sense that there were disqualifying activities and that if you engaged in them, then there would be a problem.”

Soon Hillary started talking about a hunk named Bill. “Hillary was absolutely drop-dead smitten,” Gertner recalls, veering off into a story about the time she drove to Oakland, California, where Hillary was working. “Hillary, Bill, and I were all supposed to meet for a drink in this bar. She and I met and went into the bar, but Bill wasn't there. So Hillary went and talked to the bouncer. When she came back, she said that she knew that Bill had been there. And I said, 'How do you know that?' She said, 'Well, the guy told me that he had just spent an hour talking to a guy who's going to be president of the United States.'”

After graduating, while Hillary followed Bill to Arkansas, Gertner chased her own dreams. She had offers to teach, and her credentials could have landed her at any number of well-known law firms. Instead, she chose a small, virtually unknown firm in Boston run by Harvey Silverglate and Norman Zalkind that specialized in the four Ds: draft, drugs, demonstrations, and divorce. “She had this sterling background, and we didn't think she would accept our offer,” Silverglate remembers.

In her first year, Gertner developed a thriving divorce practice to boost the firm's income. “It wasn't remotely what I wanted to be doing,” she says. “The only joy I took from that were the lesbian custody cases and being able to go into a courtroom and argue for someone who basically had no power.”

Silverglate eventually suggested that she focus full-time on her real passion: employment discrimination and criminal cases. In her first criminal case, Gertner defended a black woman who police said was speeding and didn't pull over for the officer. “I had unlimited faith in my abilities, but I really had no idea what I was doing,” Gertner says. “I had watched a lot of Perry Mason, so I had my secretary come up to me at the defense table and pass me notes that I would look at meaningfully and pass back.” She lost the case. “I would go home and cry a lot of nights those first two years,” she says. “When everyone in the room thinks you don't belong, you're not so sure you belong yourself.”

Those who watched her in her early years, however, don't remember seeing an overmatched attorney. “She may say she was overwhelmed, but she always struck me as overwhelming,” says Harvard law professor Alan Dershowitz, who worked with Gertner and Silverglate on several cases. Silverglate says Gertner was one of the best criminal defense attorneys he's ever seen. “She had it all,” he says. “She had incredible guts. She wasn't intimidated by macho police, macho judges, macho prosecutors. She had an incredible vision. She connected with jurors in ways most [lawyers] can't. She was very stylish and feminine. The prosecutor could be making an argument, and she would sit in her chair in her fiery red dress making faces, and the jury wouldn't hear a word the prosecutor was saying. It was brilliant. She was brilliant.”

Susan Saxe was a 21-year-old magna cum laude graduate of Brandeis University. She was also, the world would soon learn, a militant feminist who participated in a string of bank robberies, giving the proceeds to the Black Panthers and various underground revolutionary causes. On September 23, 1970, Saxe and her gang robbed the State Street Bank in Brighton of $26,000 and fatally wounded police officer Walter Schroeder. Saxe was put on the FBI's Most Wanted list but wasn't arrested until five years later. She was charged with first-degree murder, which carried a potential life sentence in prison.

Saxe wanted a female lawyer, and she had heard about a young, feisty, smart lawyer from Boston. “It's remarkable that she would go with a green woman lawyer,” Gertner says now. “I turned out to be terrific, but she didn't know that, and I certainly didn't.” Gertner, who was 29 at the time, says she saw a lot of herself in the 26-year-old Saxe, but she would need more than empathy to poke doubt in the government's case. In addition to the testimony of codefendants already serving time, the prosecution had intercepted two letters from Saxe — one to her father, another to her rabbi — in which she essentially confessed to the crime. But the prosecutor, the late assistant district attorney John Gaffney, decided to keep the damaging letters for rebuttal.

“I think he outsmarted himself, and I think I was underestimated,” says Gertner, who promptly rested her case without calling a single witness. That meant there was no rebuttal, and the jurors never heard about the incriminating letters. The jury deliberated for a week without reaching a verdict before the judge declared a mistrial. Saxe eventually pleaded guilty to manslaughter. “Suddenly,” Gertner says, “everybody knew who I was.”

The cases started rolling in, allowing her to choose the ones that inspired her. Her reputation soon preceded her. “She's the toughest opponent I ever faced,” says Boston lawyer Thomas Hoopes. “If you had a big enough ego, you couldn't wait to take on someone that good. And she was relentless, in addition to being able to deliver the best closing I ever heard. Some lawyers think closing arguments aren't that important, and that's probably because they don't do them well.”

Gertner wasn't afraid to take unpopular stands, including angering the very people who considered her an ally. In 1991 she argued the appeal of Brandeis student Jonathan Stockhammer, accused of raping a fellow freshman. Gertner had Stockhammer's guilty verdict overturned on appeal, successfully arguing that the defense should have had access to the woman's rape-counseling records. “But the court went much further than we had asked, saying that everyone should have access to the records in all rape cases, and I don't agree with that,” says Gertner. “That was eventually reversed, but I was picketed; I was called a boy toy and a 'so-called feminist.'”

By the early '90s, Gertner wanted a new challenge. When Clinton was elected president, she says she “toyed with the idea of going into government in any number of capacities. I put my name in the judge hopper, not really expecting to get it.” But she did, and despite her radical past, her nomination was confirmed easier than expected. She assured conservative senators that, despite her strong anti-death-penalty feelings, she “could impose the death penalty in appropriate circumstances.”

Like many observers, Gertner was unsure how she would reconcile her beliefs with the role of a federal judge. “I come to this job with strong opinions, but I'm acutely aware of them and I will struggle with them. I look at lawyering as the incredible leisure to argue creatively and passionately for outcomes that a judge can't possibly give. The challenge of [judging] is figuring out what's possible within these constraints.”

If Gertner's first seven years on the bench are any indication, a lot is possible. Even her detractors admit she is among the smartest federal judges, and a 1999 poll by Massachusetts Lawyers Weekly named her best U.S. District Court judge. She gets high marks for her fairness, laid-back courtroom, and willingness to explain her sentencing decisions in writing.

As for Gertner, she says her goal is to be nothing like the judges she faced as a lawyer. “I went before so many truly awful judges who seemed to relish making everyone uncomfortable, and with whom you felt profoundly that their finger was on the scale of justice,” she says. “I went before judges who you knew hadn't read anything, who thought they could mutter a denial and that's all they had to do, who you knew wouldn't consider your argument in a million years, even if it was justified by law. I was determined not to be one of those judges.”

She still speaks openly about some civil rights issues (she says the war on drugs makes little sense) and is a leading proponent of allowing cameras in the courtroom. She's also viewed as an expert on federal sentencing guidelines, which she and many other federal court judges believe are ineffective and unfair. “We have lost sight of how punitive we have become,” she says. “We talk in terms of bowling scores. We say, '10 to 20,' and it's not that 10 to 20 years is necessary to make the person better, because we've stopped talking about rehabilitation. Ten to 20 is what's necessary to make us feel better.”

But Gertner's willingness to speak out — especially with the media, which she calls a critical conduit between judges and the public — has led some to question her impartiality. After a jury deadlocked in the notorious 1996 Charlestown murder case of James “Jimma” Houlihan, Gertner shocked nearly everybody by lambasting the press from the bench for what she called uneven coverage of the case. She says she regrets the comment, but the experience hardly muzzled her. In February, her comments to the Herald in a case challenging the race-based school assignments of Boston students put her in the judicial hot seat. The complicated chain of events began when the Herald reported that Chester Darling, lead attorney for white students claiming discrimination, said Gertner had denied his bid to make the case a class-action suit while allowing such a suit in a similar case brought by women who said they were illegally strip-searched at the Suffolk County Jail.

“If you get strip-searched in jail, you get more rights than a child who is of the wrong color,” Darling told the Herald in reference to Gertner's decision. Gertner wrote a letter to the paper, explaining that Darling had his facts wrong, that she hadn't yet ruled on his request for the class-action suit. “In the [Suffolk] case,” she wrote, “there was no issue as to whether [the women] were injured. It was absolutely clear every woman had a claim. This is a more complex case.”

Claiming an appearance of bias, Darling — who sources say was convinced he couldn't win his case with Gertner on the bench — asked her to recuse herself. She refused. “I was merely correcting the record,” she says now. Darling appealed to the First Circuit, which sided with him, finding that her comments were “an abuse of discretion for the judge not to recuse herself based on an appearance of partiality.” Still, the appeals court was careful to say that Gertner had not acted unethically, and many lawyers and judges privately backed Gertner.

The ruling did little to clarify the increasingly dicey question of when and how a judge can speak to the press. “People were watching that decision because there is a gray area about what judges can and can't say,” says fellow U.S. District Court Judge Patti Saris. (The issue would come up more prominently in the government's antitrust case against Microsoft, in which lawyers referred to the Gertner case in arguing for the removal of Judge Thomas Penfield Jackson after Jackson made derogatory comments about Microsoft president Bill Gates to journalists while presiding over the case.)

Some speculate that Gertner's ordered recusal was aimed at shutting up the judge. “It was an outrageous decision coming from [an appeals court] that doesn't like the fact that Gertner has a bit too active a public life,” says Silverglate. “They want judges to be monks, nuns, and priests.”

Gertner is none of the above. She is a longtime activist, which makes her vocation all the more astounding to many of her friends and colleagues.

“I'm shocked she wanted to be a judge,” says Dershowitz. “She's a born advocate. She's tough and feisty. I'm shocked she would be satisfied in the passive, receiving role of a judge, but I know she feels she can do a lot of good in that role. Still, I think she'll always be a little restless in the robes.”