THE ROOKIE
On the morning of September 9, 2009, a car pulled into the Justice Department courtyard to take the government’s team to the Supreme Court for the reargument of Citizens United. Elena Kagan, the solicitor general, took the front seat and three of her deputies piled into the back. She had been confirmed by the Senate a few days before the first Citizens United argument, and the reargument would mark her debut before the justices. Kagan, at the age of forty-nine, had never so much as argued a single case in any courtroom. Citizens United would be the first time.
“C’mon guys,” she said to those in the back. “It’s my first day. Psych me up!”
The deputies looked at one another, and after a lengthy pause Malcolm Stewart whispered, “Go get ’em.”
“Ugh,” Kagan said. “You guys suck!”—and the laughter broke the tension in the car.
At precisely ten, the chief justice called Ted Olson to the lectern. Like everyone else associated with the case, he could tell from the new Questions Presented that the Court was leaning his way—heading for a ruling that was far broader than the one he originally sought. Olson argued cautiously, as if protecting a lead.
The liberal quartet of justices, recognizing that their position was probably hopeless, did their best to raise the alarm with the public if not with their colleagues. Ruth Ginsburg, surprisingly astute at judging popular opinion, brought up one potential source of future controversy.
“Mr. Olson,” Ginsburg said, “are you taking the position that there is no difference in the First Amendment rights of an individual? A corporation, after all, is not endowed by its creator with inalienable rights. So is there any distinction that Congress could draw between corporations and natural human beings for purposes of campaign finance?”
“What the Court has said in the First Amendment context, over and over again,” Olson replied, “is that corporations are persons entitled to protection under the First Amendment.” He might well have added that the principle of corporations as people went back to the strange case of Santa Clara County in 1886.
“Would that include today’s megacorporations, where many of the investors may be foreign individuals or entities?” Ginsburg went on.
Olson was ready: “The Court in the past has made no distinction based upon the nature of the entity that might own a share of a corporation.”
Kagan’s first decision was apparent even before she began speaking. Like many other members of the SG’s office (especially women), Kagan thought the woman’s version of the morning coat looked ridiculous. Through intermediaries, she had asked the justices if they would mind if she appeared in a normal business suit. None objected, and that was what she wore.
“Mr. Chief Justice, and may it please the Court,” Kagan began, “I have three very quick points to make about the government’s position. The first is that this issue has a long history. For over a hundred years Congress has made a judgment that corporations must be subject to special rules when they participate in elections, and this Court has never questioned that judgment.
“Number two—”
“Wait, wait, wait, wait,” said Scalia.
And so it went. Kagan knew she had probably launched herself on a suicide mission. Her best hope was to limit the damage, perhaps by persuading the Court to strike down this particular application of McCain-Feingold rather than invalidate the entire law. Or, as Kagan put it to Roberts, “Mr. Chief Justice, as to whether the government has a preference as to the way in which it loses, if it has to lose, the answer is yes.”
Stevens tried to help Kagan along these lines, suggesting that the Court could resolve the case with a narrow ruling. For example, the justices could create an exception in the McCain-Feingold law for nonprofits like Citizens United or for “ads that are financed exclusively by individuals even though they are sponsored by a corporation.” Grasping the Stevens lifeline, Kagan said, “Yes, that’s exactly right.”
“Nobody has explained why that wouldn’t be a proper solution, not nearly as drastic,” Stevens went on. “Why is that not the wisest narrow solution of the problem before us?”
Ginsburg did Kagan the favor of allowing her to undo some of the damage from Stewart’s argument in March. “May I ask you one question that was highlighted in the prior argument, and that was if Congress could say no TV and radio ads, could it also say no newspaper ads, no campaign biographies?” Ginsburg said. “Last time the answer was, yes, Congress could, but it didn’t. Is that still the government’s answer?”
“The government’s answer has changed, Justice Ginsburg,” Kagan replied, and the well-informed audience in the courtroom laughed. “We took the Court’s own reaction to some of those other hypotheticals very seriously. We went back, we considered the matter carefully, and the government’s view is that although 441b does cover full-length books, that there would be a quite good as-applied challenge to any attempt to apply 441b in that context.” Better late than never, perhaps, but the concession probably mattered little at this point. Especially for a first argument, Kagan was poised, self-confident, even relaxed—and doomed.
Kagan’s new subordinates in the solicitor general’s office were not surprised by her self-confidence. In theory, the solicitor general himself (Kagan was the first woman to hold the job) personally reviews every brief that goes out in his name. In reality, most solicitors general picked a few high-profile issues that interested them and basically passed off the others to the career lawyers. The SG staff quickly learned that Kagan had other plans.
On her first day as SG, almost as a courtesy, Kagan was presented with a final draft of the government brief in a numbingly tedious case called Cuomo v. Clearing House Association. (It concerned state versus federal rules regarding certain banking regulations.) The case was the type that most solicitors general gave only a cursory review. Kagan disappeared into her office with the draft and emerged hours later with a copy that seemed to have more scribbled corrections in red than typescript. Her staff knew that Kagan had not practiced law in two decades. She had never written a Supreme Court brief in her life. Furthermore, the lawyers regarded themselves, with good reason, as an elite within an elite. As Kagan’s handiwork was passed around the office, the nearly universal reaction was, “What the fuck?”
Certainly there were no complaints about Kagan’s work ethic. She was in the office seven days a week. One of her briefs went through fifty-four drafts. To prepare for her Citizens United argument, she read every case cited in every brief—which came to about three thousand pages of material. Kagan subjected herself to the same rigorous moot court ordeal that every member of the staff endured before a Supreme Court argument. To prepare for a thirty-minute argument before the justices, the advocate submitted first to an hour-long grilling from three line assistants, a deputy solicitor general, and the junior lawyer who worked most closely on the case. In addition, the SG invited to the moot courts any government lawyers who had a special familiarity with the issues in the case. Some moots had a dozen lawyers in the audience; some had forty. After the hour of rehearsal, there was then another hour spent analyzing the advocate’s answers. And the lawyers in the SG’s office went through this entire process twice before any argument. So did Kagan.
After what turned out to be a fairly brief period, Kagan’s staff came to terms with the solicitor general’s hyperactive red pen. The lawyers saw that Kagan was blunt, funny, occasionally obnoxious, and usually right. What they did not know was that Elena Kagan was working from a very specific model.
Elena Kagan grew up on West End Avenue, on the Upper West Side of Manhattan, at a time when its canyon of apartment buildings were occupied by more civil servants and social workers than, as was later the case, corporate lawyers and investment bankers. Like the Kagan family, the neighborhood was comfortable, not chic; Jewish, but not devout. When Kagan became a public figure, it was widely suggested that she had modeled herself after her father, who was described as a crusading public interest lawyer, rather than her mother, a schoolteacher. In fact, the reverse was true.
Robert Kagan had a real estate law practice based largely around the ongoing conversions of apartment buildings (like the Kagans’ own) from rentals to cooperatives. It was true that he did some work for neighborhood groups, but Bob Kagan, a gentle and modest man, was no crusader. Gloria Kagan was another story altogether.
Decades after Gloria taught her last class at Hunter College Elementary School, there are dozens if not hundreds of her former students who still dream about her. Some, clearly, have nightmares. Then as now, Hunter was one of New York’s handful of selective public schools, and it has attracted generations of multiethnic strivers. Gloria taught language arts and social studies to fifth and sixth graders. She tapped into her students’ preadolescent ambition, demanding excellence and rigor. Some students wilted, but many thrived and ascribed life-changing powers to their diminutive teacher. Of course, Gloria came of age at a time when the professional options open to a woman pretty much began and ended with teaching school (and nursing). As many who knew both of them observed, Gloria Kagan was Elena Kagan, three decades too early.
Elena made the most of the opportunities that were denied her mother. Even at Hunter, where Kagan braved her mother’s legend, she clearly wanted a life beyond the classroom. In her high school yearbook photo, Kagan posed in a judicial robe, with a gavel, and included a quotation from Justice Felix Frankfurter: “Government is itself an art, one of the subtlest of arts.” She went to Princeton, where she ran the editorial page of the college newspaper, and graduated summa cum laude in 1981. (Kagan was the third consecutive Princeton undergraduate appointed to the Supreme Court, following Alito ’72 and Sotomayor ’76. A Manhattanite, Kagan also became the representative of a fourth New York City borough on the Court, with Sotomayor hailing from the Bronx, Ginsburg from Brooklyn, and Scalia from Queens. Currently, no justice comes from Staten Island, the fifth borough.) After a fellowship at Oxford, Kagan joined the class of 1986 at Harvard Law School.*
In certain respects, Kagan’s career at law school resembled that of Obama, who arrived at Harvard five years later. Both plainly intended to put their educations to work in public life. Indeed, their law school experiences made it just as easy to predict a judicial career for Kagan as it was to foresee a political one for Obama. Because of an unaccountably poor grade in torts during her first year—the first and only B-minus of her life—Kagan did not make the law review based on grades. She earned a place through the writing competition. Also like the future president, Kagan avoided the faculty battles over Critical Legal Studies. Like Obama, Kagan was no radical, but rather a committed and serious Democrat. And like him, she sought out and went to work for Professor Laurence Tribe, the putative justice of the Democratic Supreme Court in exile (or in waiting.) Tribe chose only the best students to work for him, and only those who shared Tribe’s politics—and his ambition—selected him as a mentor.
Here, though, the parallels to Obama end. Kagan had neither the temperament nor the inclination for introspection that led Obama to write Dreams from My Father. Kagan didn’t need a whole book to outline her goals, and while she would never have been so vulgar as to voice the hope, as Alito did in his college yearbook, to “warm a seat on the Supreme Court,” her basic ambition was the same.
After law school, Kagan’s life more closely paralleled that of another future colleague—John Roberts. In every generation of lawyers, a few are widely assumed to be headed for great things, possibly even the Supreme Court. That was certainly true for Kagan and Roberts, who graduated from Harvard Law seven years before she did. The art of building a judicial career today requires talents of some subtlety, because the rules changed in recent years. In the pre–Robert Bork era, especially during the early part of the twentieth century, Supreme Court appointments went to major public figures—like Louis Brandeis, the Progressive intellectual; Felix Frankfurter, the impassioned defender of Sacco and Vanzetti; or Hugo Black and Earl Warren, politicians with national reputations. In that bygone time, a lifetime of controversy and accomplishment was all but mandatory for a potential justice. But the Bork hearings made an outspoken public career—a long paper trail, as it came to be known—more of a liability than an asset. Recently, judicial ambition has called for excellence, intelligence, and caution, all of which Roberts and Kagan had in abundance.
Today, there are just two career tracks for potential judges, one for Republicans and the other for Democrats. It is important to be identified enough with one party to have patrons, but not so closely that you have enemies. The challenge was to be partisan without seeming partisan. By clerking for Henry Friendly on the Second Circuit and then Rehnquist on the Supreme Court, Roberts committed to the Republican track. Kagan went the other way. She clerked for Abner Mikva—the same D.C. Circuit judge who later implored Obama to work for him—and then for Thurgood Marshall, who, in the 1987–88 term, was near the unhappy end of his judicial career. In the period that followed, Kagan’s career seemed a rather obvious marking of time until a Democratic administration came along. First, she spent a couple of years as an associate at Williams & Connolly. (Her duties sometimes included libel checks on the National Enquirer as well as its wackier cousin, the Weekly World News.) Next, she joined the faculty of the University of Chicago Law School. Kagan dutifully did some scholarly writing, mostly about the First Amendment, but her heart was never in the academic world. Later, in confirmation testimony, Kagan referred to herself (accurately, if immodestly) as “a famously excellent teacher,” but not long after she secured tenure, in 1995, she left for a job in the counsel’s office in the Clinton White House.
The job was the pivotal point in Kagan’s career, just as the Reagan White House changed Roberts’s life. Every office, even the West Wing, has its stars, and both future justices stood out from their peers, even in such lofty environs. Clinton used to say that anytime Kagan walked into the Oval Office, the average IQ in the room doubled. She spent two years as an associate White House counsel and two more as deputy domestic policy adviser. (Roberts also spent four years in the White House.)
As with most other presidential advisers, it was difficult to identify with precision how Kagan’s own views affected the policies of the administration. This was true of Roberts, too. Certainly Kagan played an important role in negotiating the complex resolution of lawsuits and legislation involving the cigarette industry. (Not coincidentally, it was during Kagan’s White House years that she finally defeated her own twenty-year cigarette habit.) Perhaps most importantly, the White House gave Kagan the chance to impress a generation of senior Democrats, many of whom would go on to important roles in the Obama administration. Her colleagues knew her politics—but those insights would be forever off-limits to Republicans. In the fog of government policy making, Kagan became known in the Clinton years mostly as a no-bullshit closer. Like most other staffers, she was probably more liberal than the president she served. A decade earlier, Roberts earned a similar reputation and was certainly more conservative than Reagan. These insights about the true views of Kagan and Roberts created no paper trail, but that didn’t make them any less true.
The parallel between Roberts and Kagan became especially clear at the end of her tenure in the White House. In 1992, George H. W. Bush had nominated Roberts, who was then just thirty-seven, to the D.C. Circuit, the traditional stepping-stone to the Supreme Court. In June 1999, Clinton nominated Kagan, who was thirty-nine, to the D.C. Circuit. Both nominations suggest how highly the two were regarded by their respective presidents and parties, even at such young ages. But both nominations met similar ignominious fates. In 1992, the Democrats in control of the Senate stalled Roberts’s nomination into oblivion. As for Kagan, even though the change of administrations was more than a year and a half away at the time she was chosen, the Republicans who held the majority used the same tactics to kill her nomination; Kagan never even received a vote in the Judiciary Committee.
For both Roberts and Kagan, the failed nominations appeared to be crushing disappointments. For both, as it turned out, it was the best thing that ever happened to them.
The nomination of Kagan to the D.C. Circuit, even though she failed to be confirmed, marked her as a potential Supreme Court justice. It was a tremendous honor and vote of confidence. With the Clinton administration winding down, though, Kagan faced a more immediate problem. She needed a job.
Kagan had exceeded the customary amount of time on leave to preserve her tenure at the University of Chicago Law School, but she had assumed that the job was still hers if she wanted it. She was wrong. Chicago fancies itself the most self-consciously intellectual of major law schools, and Kagan’s modest record as a scholar counted against her. She was out. (Decades earlier, Scalia struggled to receive tenure at Chicago for similar reasons; the local mandarins thought, correctly, that he preferred Washington to academia.) So Kagan scrambled and found a visiting professor position at Harvard, essentially an audition for tenure. She produced a major law review article on administrative law, her teaching was as famously excellent as ever, and she won tenure after her second year.
The key moment in Kagan’s early years on the Harvard faculty occurred when she had an opportunity to put her true skills to good use. Harvard had purchased hundreds of acres on the Boston side of the Charles River, and the new president, Lawrence Summers, was considering moving the law school there from its longtime home in Cambridge. The faculty regarded this possibility with horror. Robert Clark, the dean of the law school, named Kagan the head of a task force to study the possibility of the move—in reality, to kill it. Kagan summoned all of her bureaucratic finesse and delivered a report to Summers that all but buried the idea. Summers turned the land over to scientific projects instead, and Kagan became a hero to her colleagues on the faculty. Then Clark stepped down.
Summers, himself a former Clinton White House aide and then treasury secretary, had been a friend and colleague of Kagan’s in Washington. Though Kagan was only forty-three in 2003 and had almost no administrative experience, Summers decided to take a chance on her as the first female dean of Harvard Law School.
What happened next was one of those rare intersections of the right person at the right time in the right place. The dour Robert Clark had presided over the law school through all its enervating internal wars. Kagan, young and ebullient, swept in and cleared the air. The booming economy, at least for lawyers, helped solve many of her problems. Liberals and conservatives had battled for years for places on the faculty but Kagan had the money to reach the perfect solution—she could hire both! She gave the students free coffee, and an ice rink to use in the winter, and they loved her. Kagan’s own politics were, as ever, artful. She preserved the longtime boycott against military recruiters—employers that discriminated against gay people were not allowed to conduct official interviews on campus—but she arranged an enthusiastic welcome for the soldiers and veterans who were students. (She invented an annual Veterans Day dinner for active military students, veterans, and their spouses.) It was the kind of behavior that would look good at a confirmation hearing, and, eventually, it did.
To be sure, some of Kagan’s behavior was calculated—a studied attempt to present a bipartisan image. But her enthusiasm for debate, for the give-and-take of intellectual life on campus, was real. At a Federalist Society banquet at Harvard, she welcomed the group with the words “I love the Federalist Society”—and won a raucous standing ovation. Then she added, with winning candor, “But, you know, you are not my people.” Her elaborate celebration of the twentieth anniversary of Antonin Scalia ’60 on the Supreme Court bench was doubtless sincere—as well as very savvy. Her tenure as dean was such a success that when Summers was forced out as president in 2006, Kagan was an obvious candidate to succeed him as president of the university.
Here, though, Kagan’s politicking proved too clever for her own good. Summers’s fall as president was precipitated by his comments about the underrepresentation of women in science that were widely denounced for ignorance and sexism. At that moment, Kagan was Summers’s most high-profile female hire. As such, she could have been an important defender of his. But Kagan, perhaps sensing Summers’s impending doom, was notably restrained in offering support for her embattled boss.
This came back to haunt her. Robert Rubin, the former treasury secretary, was also a leading member of Harvard’s governing board, and he had pushed for Summers, his successor at Treasury, to be named president of the university. In Rubin’s view, Kagan had shown great disloyalty and ingratitude to Summers when she left him twisting in the wind during the women-in-sciences flap. Accordingly, Rubin made it his personal mission to prevent Kagan from becoming president of Harvard, and indeed the job went instead to Drew Gilpin Faust.
With her progress blocked at Harvard, Kagan looked for other options. She made it clear that she was backing Obama for president in 2008 and that she hoped to join him in Washington. During the transition period after the election, Greg Craig, the White House counsel designate, made a recruiting trip to Cambridge and asked Kagan what she had in mind for herself. She knew that the job of attorney general had been promised to Eric Holder, so she told Craig she wanted to be deputy AG, the person who traditionally runs the day-to-day operations of the Department of Justice. Following the disastrous tenure of Alberto Gonzales, DOJ was demoralized—just like Harvard Law School when Kagan became dean. She knew how to bring people together in a large and complex organization.
Sorry, said Craig. Holder had promised the deputy job to someone else.
What about solicitor general? he asked her.
“I’m not an appellate lawyer,” Kagan said, which was, if anything, an understatement. She had only ever been a “real” lawyer as a junior associate at Williams & Connolly. But Kagan had never run anything before she was a dean—and never worked at the White House before she went there either. SG was the most intellectually demanding job in the Justice Department, but Gloria Kagan’s daughter never lacked for moxie. “If I’m asked to do it, I’ll do it,” she told Craig. In short order, she was.
And so, in 2009, a decade after Kagan failed to become a judge on the D.C. Circuit, she was given the job that was sometimes known as the tenth justice. If she had been confirmed to the D.C. Circuit, as she had hoped to be, she might well have had a long paper trail of controversial decisions that could have disqualified her from being considered for the Supreme Court. Instead, she had a sterling—and largely apolitical—record as the savior of Harvard Law School.
As for John Roberts, his failure to win confirmation in 1992 allowed him to spend a decade as a widely respected, highly paid, and largely apolitical appellate lawyer at Hogan & Hartson. To complete the symmetry between the two lives, in 2001 George W. Bush (like his father) nominated Roberts to the D.C. Circuit, and this time, after another long delay, Roberts was confirmed. The seat Roberts occupied was the very one that Clinton had tried, and failed, to fill with Kagan.
After the second argument of Citizens United, the votes were the same as after the first one. Kagan’s advocacy had failed to break up the majority. Roberts, Scalia, Kennedy, Thomas, and Alito voted to overturn the judgment of the FEC, with Stevens, Ginsburg, Breyer, and Sotomayor (in place of Souter) on the other side. Because of the revised, and much broader, Questions Presented, Roberts was now well within his rights to lead the charge to bury decades of campaign finance law.
At the time of the first argument, in March 2009, it was not clear that Citizens United was going to be a blockbuster, so the case received a modest amount of attention. But everyone understood the stakes of the reargument. There was the inherent drama of Kagan’s debut as solicitor general and Sotomayor’s first case on the bench. (From the start, the new justice proved an able and vigorous questioner.) More importantly, the political implications of Citizens United were immense. The conservative movement had been fighting for decades to dismantle campaign finance rules. Figures as varied as Mitch McConnell, the Kentucky senator and personification of the GOP political establishment, and David Bossie, the bad-boy investigator, had the same passion for the issue. It was true that their side had some support from traditional liberal groups, like the American Civil Liberties Union (which takes an absolutist view on free speech issues) and some labor unions (which wanted to keep spending money in elections). Still, the ACLU was eccentric, and unions were losing power.
At its heart, Citizens United was a case about Republicans versus Democrats. Since the Progressive era, Republicans had been the party of moneyed interests in the United States. For more than a century, Republicans had fought virtually every limitation on corporate or individual participation in elections. Democrats supported these restrictions. It was a defining difference between the parties. So, as the chief justice chose how broadly to change the law in this area, the real question for him was how much he wanted to help the Republican Party. Roberts’s choice was: a lot.
* Kagan and I were classmates and friends at law school.