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?

A relevant comparison may be John F. Kennedy’s Catholicism—he was the first Catholic president and the last Catholic president, in the sense that since his presidency, Catholicism (indeed religion in general—vide Mitt Romney’s Mormon-ness, which played little or no role in 2012) has lost considerable valence as a political factor. Blackness is more stubbornly rooted as an identifier than religion, to be sure, but while being black probably helped Obama’s candidacy at the historic moment when he sought the office, my prediction is that it will figure much less prominently, whether on the plus or the minus side, when the next black candidate comes forward.

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)?

He certainly had transformative aspirations on entering office, and they have been seriously tempered since then. Debate as to why that has been the case will focus on the varying explanations of Republican opposition (which, simply as a matter of political craft, has been remarkably well disciplined and effective), or his own lack of political chops, whether because of inexperience or temperament.

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?

The arrest of the bottoming economic-financial crisis in early 2009. It’s hard to get credit for things that did not happen, but a moment’s comparison with the preceding comparable crisis, the Great Depression of the 1930s, reminds us what could have happened if he had not taken the steps he did, especially the stimulus bill and bank rescues and automobile-industry bailouts

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?

I don’t see a lasting legacy here—with minor exceptions (consumer protection), he has not institutionalized new powers in the executive branch; and executive orders can be easily canceled or reversed by subsequent presidents.

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’?

A relevant comparison is Eisenhower—damned from the right-wing pulpits of his day for not “rolling back” communism but now much admired for presiding over a decade of peace. Muscular foreign-policy actions make for headlines and the kinds of dramatic narratives that historians perhaps love too much, but avoiding serious mistakes, having a prudent sense of national-security priorities, as well as a sense of the fiscal, demographic, material, and political limits on this country’s scope for action in the international arena are large virtues, too often underappreciated.

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?

For whatever reason, Obama has seemed insufficiently engaged with building his party’s electoral base (and hence its capacity to sustain a long-term majority political coalition, as FDR did. He has perhaps relied too easily on perceived demographic shifts that promise a democratic-majority future without much active work to cultivate it.

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

Obama could fill out the roster of empty federal judicial appointments.

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

The Affordable Care Act.

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

Improved.

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

Obama’s speech at Osawatomie.

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

Commander-in-chief.

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

I think not—“No-drama Obama” is not the charismatic figure JFK was.

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

John Kerry, if he can pull it off, especially in Iran.

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

Drones. That’s where much of the future lies.

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

An African-American taking the oath of office.