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?

Racism is one of a handful central narratives in American history. So yes, Obama’s racial heritage is an important touchstone. And it will remain so even two decades from now.

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 fear that his presidency will not be regarded as �transformative��at least not in the sense that Obama himself used the word to describe the Reagan presidency. Ronald Reagan �transformed� America by taking it down a terribly destructive road, a path characterized by increasing inequality, disinvestment in the country’s infrastructure, and most important, a belittling of our sense of community as a nation. Contrary to the prevailing wisdom in the punditocracy, Reagan made us all smaller. Obama’s opportunity was to somehow reverse that perception and repair the damage inflicted on the country by a small band of right-wing neoconservatives who convinced white working-class males that they should align their future welfare with a political party dedicated to lower taxes and a national security state that was entitled to a major portion of the country’s discretionary budget. Obama failed to rise to this challenge.

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?

Quite clearly, Obama’s major achievement was his much-maligned �Obamacare� health-care reforms. Twenty years from now, historians will credit his presidency with bringing health insurance to tens of millions of Americans who had nothing in the way of health care. This is a formidable achievement. Presidents from Truman through Clinton failed where Obama finally opened the door to what will probably evolve into a rational single-payer health-care system.

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?

Future historians will regard this question as a canard�at least in the field of domestic issues. But I fear Obama will receive poor marks from historians looking at his unilateral expansion of presidential powers in the realm of national security. His failure to close Guantánamo, his defense of the National Security Agency’s unconstitutional surveillance activities, and his full-throated embracement of assassination by drone will become a black mark on his presidency.

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 actions abroad be judged against his recent predecessors?

Obama came to the presidency with savvy instincts in foreign affairs. And he succeeded in winding down two wars in Iraq and Afghanistan that were taking a severe toll on America in terms of both blood and treasure. But then he got dragged back into the Middle East by the so-called experts in the foreign-policy Establishment who whined incessantly that he was not doing enough about the Syrian civil war and the rise of ISIS. And yet, the tragedy is that two decades from now, no one will remember ISIS or whatever happens to the brutal Assad regime. But they will remember what Obama failed to do in Israel/Palestine. After an initial attempt early in his presidency, Obama lost all political courage and gave up on trying to persuade unimaginative Israeli leaders that time was running out for a two-state solution to the Israeli-Palestinian conundrum. Twenty years from now, historians will likely regard this failure as a tragic missed opportunity to avoid another generation or two of endless war. Obama could have confronted Netanyahu�but clearly he decided he didn’t have the political capital and so walked away. Twenty years from now, this will be seen as bad for America and Israel�and the Palestinians.

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?

I fear the Obama presidency missed an opportunity to foment a major realignment.

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?

Again, I fear that Obama surrounded himself with financial advisers who failed to seize the opportunity to reform the U.S. economy in a fundamental way. Instead, they merely stabilized the large banks that were �too big to fail.� This may well have saved the country from a deeper depression. But as a reformer, Obama compares poorly to both Teddy and Franklin Roosevelt.

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

He needs to use his executive powers to reform the immigration system, end the embargo with Cuba, and close Guantánamo. But more important, he needs to go on the road to the American people and campaign aggressively against the know-nothing, anti-intellectuals who have blocked so many of his political initiatives.

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

Obamacare.

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

As with all presidents, Obama’s standing will improve over the years. And this will be warranted. Historians will focus on the shallowness and idiocy of the Republican politicians who tapped into America’s latent racism to undermine his presidency.

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

Obama’s campaign speeches will undoubtedly resonate. But ironically, the speeches he made inside the White House will seem overly cautious and even timid.

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

He was a great orator and consoler. But he obviously felt uncomfortable as commander-in-chief.

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

Unfortunately, the drone will forever be associated with the Obama presidency.