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Authors: Jeffrey Toobin

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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.

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