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?

Obama was and wasn’t a black president. He wasn’t, in the sense that he was, first and foremost, a chief executive who defended the institutional interests of America’s “imperial presidency.” He was obsessed with secrecy, asserted executive prerogatives, and favored his standing as president even, at times, to the detriment of his own party. It is hard to think of anything he actually did where the fact that he was black, rather than the fact that he was a moderate Democratic president, seemed to matter. If anything, the fact that he is black but was primarily a moderate American president will be seen as evidence for how much the institution makes the man, not the other way around. He was, however, a black president in the sense that his administration exposes the divergence between racial attitudes and American institutions. After all, it will be remembered that a black man received the majority of votes for president, which puts paid to the notion that the majority of Americans are willfully racist. Yet, at the very same time, that president presided over a series not just of racial controversies, but controversies of a particularly brutal sort that involved not mass racial animus but rather a government enforcing unjust laws that disproportionately affect African-Americans. (Nor did the color of Obama’s skin change the fact that he imposed a more brutal deportation regime on Latinos than his predecessor). Other facts speak to the stagnation of any movement for racial progress under Obama. For instance, there is the recent research showing a widening wealth gap between whites and blacks and, more stunningly, the studies showing that schools and neighborhoods are more segregated now than they were 30 years ago. These are products of economic and social policy, undisturbed patterns of wealth accumulation, and the retreat from dealing with underlying social structures. I suspect, but perhaps I really hope, that Obama’s presidency will be seen as a turning point, in which people recognized that the law and policy of the state reinforced inequality rather than improve the ability of citizens to live together as equals. And that it was those policies, more than the color of the president’s skin, that mattered most for race relations.

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)?

I think even present historians have already abandoned the idea that Obama was or will be transformative. That he would be transformative was the initial hope, embodied in such rash actions as giving Obama the Nobel Peace Prize or the early days of the health-care initiative. But if anything, his presidency seems to be more about policy quagmires and endless qualifications. The largest transformation—of avoiding a worse recession—might be partially credible to the stimulus package, but that is not the same as a transformative legacy. Obamacare itself will not produce universal coverage, continues to be dogged by legal challenges, and most notably, only reaffirmed, rather than transformed, the New Democrat tendency to look for market solutions when possible. It might very well be the insurance exchanges, rather than the expansion of coverage, that stands as the most significant aspect of the bill. That is especially the case if the exchanges work and therefore lay the foundations for privatizing or ‘“marketizing” Medicare and Medicaid. As much as some called him a socialist, he might well be remembered as someone who de-socialized public health care.

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?

Nobody much pays attention to labor law or policy anymore, but the fact that Obama did little for the Employee Free Choice Act, and for unions generally, preferring to take his stand on health care first, sent the message that the labor movement saw little return from its considerable investment in Obama. Obama, along with the other Democratic Party leadership, decided not even to bring EFCA for a vote, which is symbolic of the way Obama will be seen as the decisive separation of labor and the Democratic Party. An image further reinforced by the fact that he has championed anti-union education-reform initiatives, like charter schools. From the standpoint of his electoral team, he was elected largely on the backs of a coalition that first flexed its muscle with Clinton—minorities, suburban professionals, all bankrolled by Wall Street—and he behaved accordingly. In the future, the setting free of the labor movement might be significant as not just the missing center of Democratic politics, but if a reconstituted labor movement decides to exercise its muscle outside the two-party system. What is misunderstood, not just by Obama but by a wide swath of liberal opinion, is that it is not enough to have a decisive president and a Supreme Court armed with the correct (rather than current) theory of law. Liberal thinking has been so shaped by the twin images of FDR and the Warren Court that it missed all of the on-the-ground, mass democratic politics that made even those modest gains possible. And at the center of that was an organized, sometimes quite militant labor movement. That has never been very well understood, but the weakening of links between the Democratic Party and labor—and the further weakening of labor itself—might be seen as more significant in the future.

Will future historians conclude that Obama weakened or strengthened 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 saved the presidency from Bush. That is too dramatic but not unfair. There was far more resistance to the excesses of the presidency under Bush than Obama. This was true at all levels—from activist lawyers, some of whom Obama brought out of the cold into the warm embrace of the Justice Department, to social movements and mass protests. Of course, that resistance to Obama has been so timid suggests something of the thinness of the anti-Bush movement, which sometimes cared more about impugning Bush and Cheney’s character than about the institutionalized excess of the presidency itself. It is worth recalling what continued or even expanded under Obama: ongoing use of torture, indefinite detention, warrantless wiretapping, drug-war policies, unauthorized use of military force, unjust policing, aggressive deportation of immigrants. If Obama made this all look more respectable or better administered, that does not mean he engaged in a dangerous escalation. There is no evidence of any serious danger to the presidency. If anything, what is most notable is that this massive security-state apparatus, inherited from the Cold War, is so out of proportion in size, capacity, and resources to any of the enemies that supposedly threaten it. The New York Police Department spying on protesters during the Republican convention is just one example of the abuses to which such an overfunded and hyperstaffed apparatus, with such small threats to deal with, is bound to perpetrate.

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’?

Although Obama is currently criticized for indecision on Russia, cover-ups with Benghazi, and lukewarm enthusiasm for the Arab Spring, I think two other legacies will be longer lasting. First, it is probably not accidental that the Arab Spring, as abortive and tragically foreshortened as it was, first occurred during a relative lull in American intervention in the Middle East. However badly Obama responded to those democratic movements once they broke out, prior to that he had turned American politics from foreign policy to domestic. That move left greater degrees of freedom for democratic movements to put pressure on their own autocratic governments without being smeared with the accusation of being agents of imperialism. That can hardly have been Obama’s intention, but it does seem to me a consequence of his foreign policy at that time, and a factor that will be clearer in time and can fairly be judged as positive. Second, surprisingly little attention is given to Obama’s Latin America policy, outside normalization with Cuba and his relation Venezuela. But Latin America has been paying attention. On that front, Obama’s support for an anti-democratic coup in Honduras, increasing and irrational hostility to Venezuela, the outrage of making no effort to deal with the Supreme Court’s hideous ruling against Argentina (look it up), willingness to let Mexico and Colombia pay the price for the drug war, and intensification of border policing and deportation will be seen as something near inexcusable. That is true no matter what the final assessment of normalization with Cuba ends up being. Taken together, Obama’s Latin America policy will be seen as the continuation of America’s desire to dominate the Western Hemisphere, not live together as equals.

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?

American elections are impossible to predict. I have been through too many elections in which one or the other party is consigned to the dustbin of history to make any such foolish prediction about who is more likely to win in the future. The durability of coalitions is a little more foreseeable, but only on the order of a few decades. There, I think we will see Democratic coalitions that bank on negative appeals to minorities, especially blacks and growing numbers of Latino voters, that amount to something like “Republicans are racists.” They will be coupled together with liberal professionals, whose interests are more directly represented in the Democratic Party, along with appeals to sections of capital, especially Wall Street. I suspect that Democrats will be able to win enough presidential elections and control enough Congresses to stick with that strategy. In general, the Democrats will be overconfident that demographic trends favor them and will assume they need no dramatic changes in coalitional strategy. It is quite possible there will be more innovation in Republican strategies and attempted coalitions precisely because the demographic trends are against them. I don’t quite know what those strategies will be, but I expect the surprises will come in who comes to support the Republicans. The sometimes predicted left-field realignment coalition between the left and the libertarian right into a civil liberties, anti-authoritarian, third-party movement will remain with its predictors—on the internet.

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?

It is easier to give credit for what did happen than what didn’t. Who knows how much deeper the recession would or wouldn’t have been—likely a bit but not massively. We do know that during the first three years of the “recovery,” the top one percent captured 95 percent of the income gains and that, by now, the top one percent fully recovered all lost income while the bottom 99 percent are barely above stagnation. Inequalities in wealth are even more extreme. We do know that unemployment has returned to its pre-crisis level—just over 6 percent—but that is partly an artifact of about 3 to 4 percent of the population suddenly dropping out of the labor market after 2008. You put them back in, and it’s still 10 percent. The only unequivocal recovery has been in the stock market. So whatever Obama might or might not have saved us from, he presided over an extremely lopsided “recovery” and will certainly be remembered for that. It is no doubt true that Obama is not solely responsible for economic policy. It is easy to make a fetish out of the presidency and his power, a fetish the modern presidency actively encourages. Congress, too, had a major hand in a one-off stimulus, bailing out the banks and then ensuring nobody else got much of anything. But what Obama may legitimately be held responsible for in the future is having been uncomfortable even talking about inequality. He actively superintended one of the most lopsided recoveries in history.

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

I am tempted to say he should pardon every person in jail on a drug- or immigration-related charge. But I would settle for something more modest. Perhaps he could just say he made a mistake talking about meritocracy and claiming that everyone getting a college degree is the key to success, job security, and middle-class life. The ten occupations that will add the most new jobs are in health, retail, and construction. Nearly all of them require no higher education, and they pay poorly—barely above official poverty rates. Getting a college education will do nothing to improve the standard of living of that growing body of workers, though unionization would. It would make a difference if Obama were simply to acknowledge that fact, recognize America’s class structure, admit that education, alone, is not going to solve this problem, and say explicitly that those who didn’t get that education do not deserve their underpaid, insecure employment. His meritocracy nonsense implies that those at the top deserve their ridiculously inflated incomes, while those at the bottom deserve to be at the bottom because they failed to seize opportunities. Obama likes to talk about Lincoln, but Lincoln thought that the opportunity for independence and security should be available to all. Obama’s legacy will be saying that such opportunities should be scarce and the object of fierce competition.

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

Obamacare—for better but mostly worse, it is his signature policy, the stamp he put on American politics. Though a close second will have to be drawing down American forces in Iraq and Afghanistan. I suspect the other obvious candidate—the killing of bin Laden—will seem less consequential over time.

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

Improved—it is hard to imagine it getting worse than it is now, and imperial nations in decline tend to remember the past fondly.

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

Everyone will remember the phrase “Yes, We Can” and his speech in Cairo. There was always something rather sinister about the phrase “the surge.” I am sure the Afghans, at least, will remember it.

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

Campaigner: Key features of his personality—calmness, unflappability, oratory skill—played better in a campaign than as president. As actual chief executive, the first two qualities came across as indifference, even stoic impermeability to the urgency of politics, and his speechifying over time became more and more halting.

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

No, perhaps because it is more difficult, in this media age, to sustain a certain image. Obama’s image wore off rather quickly, while he became just as quickly identified with specific policies and events. Also, unlike JFK, Obama did not so much craft an image as attempt to make himself a cipher onto which everyone could project their own fantasies.

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

It is hard not to go with Hillary Clinton, but it is more accurate to say Rahm Emanuel. Emanuel had his hand in everything, not just Obamacare. He was the New Democrat attack dog who did the insider dirty work while Obama tried to rise above, or at least stand back from, the fray.

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

The reduction of troops on the ground. It set a new dynamic in play in Afghanistan and Iraq, while also freeing up troops for whatever wars and interventions the U.S. fights in the future. The drones are a terrifying image of techno-imperial domination, but they are not the core of American power abroad.

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

The symbolic image that exists only in our imagination because we never saw it: Osama bin Laden being dumped in the ocean.