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Authors: Jeffrey Toobin

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This was an Obama credo of sorts. To him, the courts were (or should be) static in their protection of basic rights, but he was not going to push judges and justices to create new ones. In this way, Obama differed from both liberal heroes like Thurgood Marshall and conservative icons like Antonin Scalia; they believed that the courts could deliver social change. Obama did not, and this diffidence about the role of the courts shaped his professional life and, later, his presidency.

After Obama’s defeat in the 2000 congressional race, his fortunes turned around. Just as he started paying more attention to the job in Springfield, the Democrats took control of the state senate in 2002, so he had the chance to accomplish something. He sponsored or cosponsored twenty-six successful bills in a row, including tax cuts for the lower middle class, health care for poor children, a ban on the diet supplement ephedra, and a careful
compromise on racial profiling by the police. (The bill required police to record and report the race of every motorist who was stopped.) Obama decided to run for an open U.S. Senate seat in 2004. His good fortune multiplied. The candidacy of his leading opponent in the Democratic primary imploded in a sex scandal—and, incredibly, the candidacy of the Republican initially nominated to face him
ended in a sex scandal. He wound up facing only nominal opposition in the general election. Even though Obama was still just a state senator, he gave the keynote speech at the Democratic Convention in 2004—and it was a smash. His memoir was reissued and became a best seller.

By the time Obama arrived in Washington in 2005, he was a
national figure—but on his own terms. He was, of course, the only African American senator at that moment, but he went out of his way to define himself in other ways. He joined the Committee on Foreign Relations, not the Judiciary Committee, which is the principal guardian of the civil rights laws and a seat the only black senator might have been expected to take. Obama dabbled in legislating, but basically used his Senate office to prepare to run for president. He wrote a campaign-style manifesto,
The Audacity of Hope
, and turned a book tour into a testing-the-waters campaign. (The title of the book came from a sermon by his preacher in Chicago, Rev. Jeremiah Wright Jr.)

As Obama began playing to a statewide and then a national audience, he made some adjustments in his stands on the issues, notably gun control. When he was running for the state senate in Chicago, he took the conventional view of inner-city politicians that gun ownership should be sharply limited. In his first race for state senate he even said in a questionnaire that he supported “restrictions on the sale and possession of handguns.” (Obama later said a staffer filled out the form.) Still, in the state legislature, Obama continued to vote in general support of restrictions on gun use and ownership.

But when he ran for the U.S. Senate in Illinois, a state with a thriving hunting culture, Obama began subtly turning away from his previous position. Like many Democrats nationwide in the post-Clinton era, Obama recognized that to push gun control was to court electoral disaster; the laws would never pass and the candidates who supported them would never win. Still, Obama had not at this point migrated entirely to the individual rights views of the Second Amendment. When Alan Keyes, the hapless Republican who wound up running against Obama in the 2004 Illinois Senate race, challenged Obama in a debate on his beliefs about the Second Amendment, Obama steered the conversation in a different direction. Obama said nothing about the Constitution but only that he believed in “common sense gun safety” measures like a ban on assault weapons.

But conservatives had succeeded on gun control and the Second Amendment in the new millennium the way liberals had won on school desegregation and equal protection in the 1960s. Through the use of politics, the courts, and the broader culture, each side in turn had changed the understanding of the Constitution. In both cases, the political victories were so overwhelming that opposition became futile.
By the 1970s, no serious politician advocated segregated schools; by 2008, no serious presidential candidate—at least one who hoped to win—advocated the traditional conception of the Second Amendment.

So, after Obama launched his presidential campaign in 2007, he began speaking out in support of an individual right under the Second Amendment. The mode of Obama’s expression, which he repeated throughout the campaign, revealed the nature of the conservative ideological victory on this issue. As Obama put it in a debate with Hillary Clinton before the Pennsylvania primary, “As a general principle, I believe that the Constitution confers an individual right to bear arms. But just because you have an individual right does not mean that the state or local government can’t constrain the exercise of that right, in the same way that we have a right to private property but local governments can establish zoning ordinances that determine how you can use it.” It was, characteristically for Obama, a cautious position, but still an unmistakable endorsement of the individual rights theory. The future president picked his fights—and chose to avoid this one over the Constitution. It wouldn’t be the last time, either.


n gun control, Obama played to his instinct for compromise and conciliation. Politics often lends itself to these sorts of solutions. But sometimes a senator, like a justice, simply has to make a decision. On one of these occasions, during his brief career in the United States Senate, Obama had a real struggle: the nomination of John Roberts to be chief justice of the United States.

Obama and Roberts had met only once, in the fall of 2005. Roberts had already called on most of the senators when he finally made it to Suite 713 in the Hart Building, the remote lodging to which junior senators like Obama were assigned. Roberts was exceptionally good at these courtesy calls: knowledgeable but not arrogant, open but noncommittal. As far as Obama was concerned, the judge had a lot going for him. Obama valued credentials, and Roberts had the best of their shared generation, not least a Harvard Law degree. For his part, Roberts had the same instincts about Obama. Judicial candidates making the rounds of senators quickly suss out the gasbags from the players, and there was no doubt in Roberts’s mind of the future president’s intelligence.

In the end, Obama’s vote on Roberts had little to do with the nominee’s qualifications, or even Obama’s feelings about him. The senator consulted some of his law professor friends, like Laurence Tribe, at Harvard, and they told him that Roberts was about as good as anyone could expect from the Bush administration. The judge was conservative, Tribe said, but perhaps he’d keep an open mind. But the advice that mattered most to Obama came from his own chief of staff, Pete Rouse, a Washington veteran. Rouse told Obama, in effect:
Cut the
shit. You can’t run for the Democratic nomination for president and also vote to confirm George Bush’s nominee for chief justice. The Democrats who vote in primaries care too much about these issues—like abortion rights—for you to vote for
a justice who might overturn
Roe v. Wade. Obama couldn’t disagree.

So Obama voted no, one of only twenty-two negative votes. (Obama’s future rival Hillary Clinton voted the same way.) Still, Obama’s statement on the Senate floor reflected his ambivalence on the nomination. “There is absolutely no doubt in my mind Judge Roberts is qualified to sit on the highest court in the land,” Obama said. “Moreover, he seems to have the comportment and the temperament that makes for a good judge. He is humble, he is personally decent, and he appears to be respectful of different points of view. It is absolutely clear to me that Judge Roberts truly loves the law.” Exaggerating slightly, Obama said 95 percent of cases at the Supreme Court were easy; “a Scalia and a Ginsburg will arrive at the same place most of the time.” (About a third of cases are unanimous each year.)

Obama went on: “What matters on the Supreme Court is those 5 percent of cases that are truly difficult. In those cases, adherence to precedent and rules of construction and interpretation will only get you through the 25th mile of the marathon. That last mile can only be determined on the basis of one’s deepest values, one’s core concerns, one’s broader perspectives on how the world works, and the depth and breadth of one’s empathy.… In those difficult cases, the critical ingredient is supplied by what is in the judge’s heart.

“I talked to Judge Roberts about this. Judge Roberts confessed that, unlike maybe professional politicians, it is not easy for him to talk about his values and his deeper feelings. That is not how he is trained. He did say he doesn’t like bullies and has always viewed the law as a way of evening out the playing field between the strong and the weak.”

But that wasn’t enough for Obama. “The problem I had is that when I examined Judge Roberts’s record and history of public service, it is my personal estimation that he has far more often used his formidable skills on behalf of the strong in opposition to the weak. In his work in the White House and the Solicitor General’s Office, he seemed to have consistently sided with those who were dismissive of efforts to eradicate the remnants of racial discrimination in our political process. In these same positions, he seemed dismissive of the concerns that it is harder to make it in this world and in this economy when you are a woman rather than a man.”

Quickly, though, right after Obama voted no, he engaged in a characteristic gesture. The very next day, Obama posted a statement on DailyKos, the website that served as the unofficial home of the Democratic Party’s Netroots, defending his colleagues who voted yes. The point Obama made was a familiar one for those who had followed his thinking about the courts. “There is one way, over the long haul, to guarantee the appointment of judges that are sensitive to issues of social justice, and that is to win the right to appoint them by recapturing the presidency and the Senate,” Obama wrote. “And I don’t believe we get there by vilifying good allies, with a lifetime record of battling for progressive causes, over one vote or position. I am convinced that, our mutual frustrations and strongly held beliefs notwithstanding, the strategy driving much of Democratic advocacy, and the tone of much of our rhetoric, is an impediment to creating a workable progressive majority in this country.” As usual with Obama, it was about elections, not lawsuits.

Four months later, when Alito came up for a vote, that was an easier call for Obama, and for most other Democrats. Alito had little of Roberts’s charm, and his record on the bench offered no promise of moderation. Like Roberts, Alito had been a young recruit to the Justice Department during the Reagan administration, first in the office of the solicitor general and then in the office of legal counsel. He was appointed United States attorney in his native New Jersey in 1987 and then three years later, at the age of forty, won appointment to the Third Circuit. There he never varied from the conservative line and made a particular name for himself as an opponent of abortion rights. Shortly after Alito joined the Third Circuit, he voted to uphold a Pennsylvania law that required wives to inform their husbands before they obtained an abortion. It was this provision in particular that offended O’Connor and prompted her vote to overturn the law in the famous
Planned Parenthood v. Casey
decision of 1992, the ruling that preserved the core of
Roe v. Wade
. For this reason, Alito was an especially fitting replacement for O’Connor—because he reflected how much the Republican Party had changed since her appointment. From the moment Bush named Alito, it was clear what kind of justice he would be. For this reason, Obama voted no, but Alito was confirmed by 58 to 42.


Obama’s intelligence was tempered by a grace and serenity, but he was matched in these qualities by the new chief justice. From his earliest days, Roberts was an enormously successful student who excelled without calling a great deal of attention to himself. He had taken enough advanced placement tests at La Lumiere to skip his freshman year at Harvard, and it took him only three years to graduate summa cum laude. Three years later, in 1979, he earned his degree from Harvard Law. But Roberts’s professional career was about ideology as much as brilliance and charm. At every step, Roberts’s work mirrored, and hastened, the conservative movement in the law.

Roberts’s two judicial clerkships traced the trajectory of the Republican Party at large. Henry Friendly was appointed to the Second Circuit by Dwight Eisenhower, in 1959. Friendly and his circle of lawyers were based in New York, and many received their start in law, and politics, when they worked for Thomas E. Dewey, the crusading local prosecutor and governor who nearly won the presidency in 1948. They were close to Wall Street and big business—Friendly had been general counsel to Pan American World Airways—and they took a progressive attitude toward the racial struggles that were convulsing the country. On the Supreme Court, this group was represented by John Marshall Harlan II, a frequent dissenter during the liberal heyday of the Warren Court. Friendly believed in respect for precedent, gradual change, and almost scientific expertise in the law. Friendly was as far from a Scalia-style conservative as he was different from a Brennan-style liberal. The politics of Friendly’s law clerks ran the ideological gamut.

BOOK: The Oath
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