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’s race was a huge factor in his getting the Democratic nomination in the first place, and in 20 years, his supporters will be less loath to admit that. Obama’s race was also a factor in mobilizing a portion (but far from all) of the hostility he encountered from the right. This is not to say that people were overtly or consciously racist (though some of course were). But the forms that the opposition rhetoric took—gripes about handouts for the undeserving—were shaped by racial stereotypes and prejudice. We should not forget that the same far-right elements were every bit as hostile to Bill Clinton, who was accused of being complicit in murder and other absurd scenarios.

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 do think that “history” remembers achievement. Obama’s achievements are mainly the economic recovery (which is sort of an achievement—not huge, because it has left so many people behind), and the health-care bill, the luster of which will probably diminish over time as people continue to remain frustrated with the system of private health insurance that Obama chose not to disturb. Whether or not you think that Obama could have (à la Clinton, Reagan, and Eisenhower, to name three) found ways to work constructively with the opposition party, the cries of “obstructionism” won’t get him far in the eyes of historians. They’re true, of course, but they are not the end of the story. Presidents with thin records of accomplishment—whatever the reason for it—simply rate fewer paragraphs in the textbooks.

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?

How many people, when Bill Clinton left office, said, “His counterterrorism policy will get far more scrutiny than it has thus far”? I think we have seen in foreign policy an almost complete abdication of long-range strategy (with the small exception of the “pivot” toward Asia). It seems very plausible to me that historians will wonder why on Earth Obama trusted in people like Ben Rhodes and Denis McDonough—political operatives who had no executive, only congressional, experience. There is no Kissinger, Brzezinski, Scowcroft, Albright, Holbrooke; the foreign-policy experts have been marginalized, the political people enthroned. Vali Nasr’s critique may well come to seem prescient.

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?

I do not think that his executive actions are out of keeping with those of his predecessors in the 20th century, especially since FDR. I would expect that Bush Jr.’s presidency, not Obama’s, will be remembered for reviving the “imperial presidency.” Obama did not surrender the powers Bush had arrogated to the White House—but then, presidents rarely do.

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’?

Mostly poorly. In the first term, he showed signs of being a Clintonian internationalist, willing to intervene multilaterally and with legitimacy in places like Libya. The killing of bin Laden and weakening of Al Qaeda will stand as achievements. But the Arab Spring went awry, and Obama had no policy to foster democracy in the Arab world. Obama also misplayed his hand on Israel in the opening months of his presidency, alienating Netanyahu, and he has never recovered. Perhaps the key moment will be his backing down from his plan to attack Assad; he lost credibility in the eyes of the world and emboldened tyrants like [Turkey’s]Erdogan. The failure to encourage moderate rebels in Syria was also a (not the only!) contributing factor to the rise of ISIS, which the administration foolishly declined to regard as a threat until it was too late.

Judged against Bush? Bush was a complete disaster, reckless and arrogant. But Obama overcorrected with a surfeit of caution in foreign policy and withdrawal from the world. Judged against Clinton? Clinton’s strengthening of NATO, his emphasis on diplomacy over military action, his rehabilitation of America’s image abroad, his limited interventions in Bosnia and Kosovo—all look much better than Obama’s foreign policy. As they did in the 1930s, Americans years hence will regret having tried to avoid involvement in the world’s problems. It cannot be done. It need not be done militarily, but it has to be done with more gusto than Obama has shown thus far.

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 realignment began in 1992, when Clinton won back the Reagan Democrats. Obama got some of them in 2008 but fewer in 2012. He has mostly benefited from generational and demographic change, not by winning new adherents to the party. It is very hard to predict where this will go. Arguably, since 2000 (or even since the 1980s), we have been a 50-50 nation, and we seem likely to remain thus deadlocked for a while.

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?

Both. Obama (and, to be fair, Bush a little bit) did intervene to stop the worst from happening. But when he took office Obama was so afraid of sending the recently recovered stock market back down that he trusted in Geithner instead of pursuing more radical and populist measures (which he could have done, given the fluidity of the political environment). He will be credited with averting disaster but faulted for having missed a big opportunity.

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

Strike a major tax deal that includes lifting the cap on taxable Social Security earnings. If he were to turn the Social Security tax into a progressive (or non-regressive) one, it would be a major achievement, perhaps obtainable in return for a corporate tax cut.

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

Righting the economy in 2009.

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

His 2008 speech on race in Philadelphia

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

Vessel of hopes.

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

Tim Geithner.

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

Reduction of troops.

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

The time he invited Bill Clinton to brief the press, and then left while Clinton happily yakked away. (Okay, not the most lasting, but a highly symbolic one …)