How much will Obama’s being black matter in the end? In, say, 20 years, will it be a major or minor aspect of his presidency and, to the extent that it will matter, in what specific way will it matter most?

I fear Obama’s blackness will matter largely as a continuing excuse for national self-congratulation, at least among the punditocracy. To historians, Obama’s being black may also help explain his timidity on policy matters, his willingness to conform to the Washington conventional wisdom. He had risen to the top of what Americans like to call a meritocratic system�in part through his own exceptional talent, intelligence, and ambition but also through his ability to play by the Establishment rules of credentials and networking. His presidential campaign rose to unprecedented heights of oratorical and analytical power�especially the Philadelphia �Speech on Race� when he identified racial divisions as the reason workers failed to recognize their common class interests. No American politician running for high office had said anything like that since the Populist Tom Watson in the 1890s. Yet after his campaign had won him a democratic mandate, Obama immediately reverted to his prudential self. His blackness, rather than reinforcing an outsider’s perspective, became little more than a marker in the feel-good game of identity politics. The episode shows how detaching race from class and other sources of social inequality can be a prescription for apolitical vacuity.

Will future historians blame Obama for not getting more done in a climate of Republican obstructionism, or will he be given a pass for it? More generally, to what degree will his presidency be seen as transformative (the word he used to describe the Reagan administration)?

It’s hard to imagine Obama’s presidency could be seen as transformative when it stayed so carefully inside the Washington consensus. No one can deny the power of Republican obstructionism, but it is important to remember that Obama swept into power with a decisive electoral triumph and Democrats in control of both houses of Congress. Yet he failed utterly to take advantage of this opportunity to steer the country away from the failed policies of the past. He began by appointing Bob Gates, Hillary Clinton, Timothy Geithner, and Larry Summers�all guarantors of continuity. Though he was one of the most educated and thoughtful presidents we’ve had in a long time, Obama failed to educate the public on fiscal matters�particularly on the distinction between government and household debt. As early as the State of the Union Address of 2010, well before the Republicans had retaken the House of Representatives, he was saying that just as ordinary Americans had to tighten their belts in hard times, the government had to do so too. This ruled out the kind of countercyclical spending that would have had a better chance of ending the recession and reasserting the possibilities for economic democracy. He ceded most of the intellectual territory to the advocates of austerity, long before he had lost Congress to them. On foreign policy, Obama showed the same inability to move beyond the boundaries of inside-the-beltway convention. His Nobel Prize acceptance speech made clear that he was as committed as his predecessors to the myth of American exceptionalism�the notion that the United States had a unique (perhaps divinely ordained) responsibility for world leadership. And the exceptionalist faith has been and remains the main ideological justification for default-setting military intervention abroad. With a few faint and fitful exceptions, the Obama administration has been all about continuity, not change�still less transformation.

In assessing Obama's historical legacy, what do you believe will be the aspect of his presidency that is currently least understood or misunderstood? In other words, for better or worse, what single thing looks smallest now but will matter most to future historians?

No one wants to talk about Obama’s continuation of Bush’s war on civil liberties. But this may prove to be his most lasting legacy�the last time an American president had the opportunity to resist the rise of the surveillance state and refused to do so.

Will future historians conclude that Obama weakened or strengthen the office of the president? Will the policies he enacted without congressional cooperation represent a strategic victory or a dangerous escalation of executive power?

Obama’s record here is mixed but mostly disastrous. The new immigration policy and the reopening of diplomatic relations with Cuba are strategic victories, or so at least we can hope. But the continuation (and in some cases expansion) of Bush-era national-security policies is the bitterest disappointment of his presidency. I did not accept his messianic campaign rhetoric at face value, but I did believe�based on his record as well as his statements�that he promised genuine deliverance from the coup d’etat that was unfolding under the Bush administration. He was a constitutional lawyer who seemed to care deeply about civil liberties. What a fantasy that hope proved to be. Available evidence suggests that despite official denials, Obama has continued the policy of �extraordinary rendition� (or torture by proxy) begun under the Bush presidency. His Department of Justice has also expanded warrantless surveillance, creating a dragnet under the NSA that flagrantly violates the Fourth Amendment’s prohibition of search and seizure without �probable cause.� It has also prosecuted whistleblowers even more vigorously than the Bush Department of Justice did, breathing new life into the Espionage Act�a vile relic of Wilsonian repression during World War I. With the collaboration of Congress, the president (as �commander-in-chief�) has claimed unprecedented discretionary authority to assassinate suspected terrorists, including U.S. citizens, without any concern for traditional constitutional concerns about due process or reasonable doubt. No wonder he was so eager to �move forward� rather than prosecute the felons of the Bush administration. His administration remains complicit�sometimes passively, sometimes actively�in many of the same crimes. Obama’s unconstitutional aggrandizement of executive power constitutes his most serious failure of leadership.

Assuming no dramatic shift in world events between now and 2016, which parts of Obama’s foreign-policy tenure will be judged most positively and which most poorly? Overall, how will his actions abroad be judged against his recent predecessors’?

During his campaign, Obama said that he had opposed the Iraq War �in conception as well as execution.� This naturally led many voters to expect a shift away from the imperial adventurism of his predecessor. But the appointment of Gates and Clinton was an early sign of how vain that hope would be. The Oslo speech was another. To be sure, Obama made a sustained effort to disentangle U.S. forces from Iraq and then turned toward Afghanistan, as he had promised he would. But he remained largely in thrall to the generals’ counterinsurgency fantasies (�government in a box,� etc.)�none of which produced the results their proponents predicted. He acquiesced to the bellicose Clinton in the misbegotten assault on Libya, which left that country a shambles, exacerbated chaos throughout the region, and contributed to the civil war in Syria. From time to time, he revealed flickers of independence: his announcement that it was time to turn to �nation-building at home,� his West Point speech counseling the need for restraint in foreign policy, his efforts to reach a diplomatic understanding with Iran, and his resistance to Clinton’s plan to arm the �moderates� in Syria. This last was perhaps the high point of his foreign policy, when he asked: When has the strategy of arming selected insurgents ever worked in the past? The answer, of course, was: Never. This was the only time this supposed pragmatist invoked the core of the pragmatic philosophical tradition�the insistence on judging ideas by their probable consequences. But this was an uncharacteristic show of backbone. The overall pattern is that Obama has made several mostly ineffectual attempts to resist the foreign-policy Establishment but in general has shared their assumptions and caved in to their demands.

Will the Obama years come to be seen as a major realignment in Democratic politics? As a historian, how would you predict the longevity of his coalition?

The Obama years represent the fusion of identity politics and neoliberal policy�government in the service of crony capitalism. The Democratic campaign strategy will continue to be to offer a laundry list of gestures toward identity-based interest groups while offering no real alternative on economic or foreign policy. The same elites will contribute to both parties. The Democrats may have a few more contributors from Hollywood and Silicon Valley, but they will continue to have plenty from Wall Street (especially if Clinton is the candidate). Younger, multicultural, and multiracial voters will find the identity politics appealing and may help to swing elections toward the Democrats, especially in presidential years. But as long as the Democrats offer no substantive alternative to the Republicans, they cannot expect to appeal to younger voters on the basis of party identification alone. And sooner or later the magic of identity politics will fade, unless it’s accompanied by debt relief, an increased minimum wage, and other policies that meet voters’ social as well as psychological needs. Obama’s timidity has given younger and less affluent Americans more reason than ever to feel cynical and alienated from mainstream party politics.

Will future historians concur with the Administration�s own narrative of having saved the country from another Great Depression? Or will Obama�s economic legacy be seen as a lackluster performance, or worse, a failed attempt to reform the U.S. economy in any meaningful way?

Obama had an opportunity to change the conversation on economic policy, to wrest it away from the deficit hawks and institute a left-Keynesian plan for recovery through increasing aggregate demand. Of course that would have posed the (perhaps insoluble) problem of how to do this in an ecologically responsive way, but we never had an opportunity to have that debate. Instead of confronting the crisis with the kind of boldness his campaign had promised, Obama proposed a stimulus package that was a good start but insufficient to do the job. Whether he could have accomplished more is an open question, but the point is he never tried. On the contrary, he yielded the upper hand to the risibly right-wing (but allegedly bipartisan) Simpson-Bowles Commission. Any further stabs at Keynesianism would focus entirely on stimulating investment through monetary policy rather than stimulating consumer demand through fiscal policy. Government spending would continue to be viewed as analogous to household spending. No one would make any attempt to restore the draconian cuts in state support for higher education and other public services that occurred in response to the recession. Unemployment figures would drop, but no one would ask what kind of jobs were being added to the economy. In fact, they would be increasingly low-wage, short-term, and precarious�which has been the overall trend since the rise of neoliberalism under Reagan in the 1980s. No wonder most Americans are wondering: What recovery?

What single action could Obama realistically do before the end of his term that would make the biggest positive difference to his historical legacy?

Appoint a special prosecutor to investigate the crimes of Bush’s CIA�and his own.

What will be seen as Obama's single most significant accomplishment?

The easiest answer would be Obamacare, but it is such a characteristically muddled compromise with the health-insurance industry that I would pick his (largely ineffectual) attempts to resist the foreign-policy Establishment.

Will Obama’s reputation have improved or declined in 20 years?

It may well have improved because public disappointment in his failed promise will have faded and his successors will probably be so mediocre (judging by the current crop of likely candidates).

Which of his speeches and phrases will be the most enduring?

The Philadelphia �Speech on Race��though he gave a lot of other great ones during the campaign.

In which presidential mode was Obama the most effective: orator, legislator, commander-in-chief, consoler of the nation, or some other mode?

He was most successful in the oratorical mode�but that was while he was a candidate.

Will the image of Obama overshadow his accomplishments, in the manner of JFK?

Probably: His accomplishments are few and far between, but he has an attractive family; he is also smart, articulate, witty�and of course, the first black president.

Who will be seen as the most consequential member of his Cabinet or senior staff?

I fear it will be Hillary Clinton, who is using her term as secretary of State as a springboard for the presidency.

Which will prove to be more significant: the reduction of troops on the ground or the increase in the use of military drones?

The use of drones will have a long-term impact, encouraging ill-advised interventions by making them seem cost-free.

What will be the most lasting symbolic image of the Obama presidency?

That brief, shining moment when he addressed the cheering crowd in Grant Park, Chicago, after his election.