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 question the assumption that Republicans were guilty of �obstructionism.� There are strong arguments that Congress owes the president some deference on matters that are especially close to his constitutional authority, such as foreign affairs and appointments. But it has no duty to pass his bills on core issues of legislative responsibility, particularly taxing and spending. Rather than partisan opposition, the real story is the shrinking of the legislative branch, in favor of a model of governing in which Congress passes vague enabling statutes and leaves executive agencies to work out the content of the law.

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?

Historians and political scientists will emphasize the continuity between the Obama and Bush administrations. Both presidents made bold claims of executive authority in pursuit of an aggressive foreign policy. And both steered through Congress expensive health-care entitlements that will also make a lot of money for private firms: Medicare Part D in Bush’s case; the ACA in Obama’s. I haven’t picked these issues at random. Corporatist health-care policies, American military hegemony, and centralized education reform are elements of a bipartisan consensus that remained fairly stable over the last ten or 20 years. In this respect, conservatives who criticize Obama as a radical are wrong�as were progressives who denounced Bush in similar terms. Both represented in a fairly consistent way the conventional wisdom of our time.

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?

Like most of predecessors going back to T.R., Obama has enthusiastically asserted the prerogatives of the executive branch at the expense of legislature. Debates over war powers have attracted most of the attention. The greater threat to republican government, however, is the growing ability of executive and administrative agencies to determine what the law means.

Obamacare is a good example. Although it was nominally approved by Congress, the real mechanics of the law are being worked out by the alphabet soup of bureaucracies that the ACA set up. As Nancy Pelosi put it, �We [the House of Representatives] have to pass the bill so that you can find out what is in it away from the fog of the controversy.�

Historians will be in a better position than we are to say whether this procedure led to the right outcomes: higher rates of insurance and lower costs. But it’s hard too see it as an exercise in meaningfully representative government.

An emphasis on the military aspects of executive power can lead to the conclusion that we live under a sort of postmodern emperor who governs by personal fiat. I’m more concerned that the institutional strength of the executive branch will lead to a kind of administrative despotism in which the president himself will have little influence over the laws and regulations under which ordinary citizens have to live.

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?

As Michael Lind has argued, Obama’s coalition is the culmination of the �New Politics� that the national Democratic Party has pursued since the late ’60s. This strategy is based on appeals to the young, the highly educated, racial minorities, and single women, at expense of the white working and middle classes. Unlike the New Deal, the core of these appeals is not economic fairness. Rather, it’s social equality and liberty in personal conduct.

The New Politics was failure in 1972 because there weren’t enough voters in these categories to carry McGovern to victory. It’s a winner today because there are a lot more of them. If the demographic composition of the electorate had been the same in 2012 as it was in 1980, Romney would have won in a landslide. But it wasn’t and he didn’t.

Even though it’s numerous, however, the Obama coalition is fragile. Lacking the organizational base that the unions and urban machines once provided Democrats, the New Politics depends on rhetorical appeals to bring out individual voters. That can work in presidential years, particularly with a historic figure such as Obama on the ticket. It doesn’t appear to be successful in off-years. And we’ll see what happens with a less inspiring candidate.

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’s hard to say what would have happened if the administration had failed to secure the stimulus and funds to insure international liquidity in 2009 and 2010. But the bottom did not fall out of the economy. The administration deserves credit for this.

Tough as things are, the U.S. economy is also doing better than other countries’. That’s partly due to the energy boom, which is sheer luck. But Obama’s opposition to the kind of austerity policies that are causing so much pain in Europe also has something to do with it.

There are two major blemishes on this relatively successful record. The first is that Obama has done nothing to reform entitlement spending, which most experts agree to be based on outdated demographic and economic assumptions. Without significant changes, Social Security, Medicare, and Medicaid will go broke in a matter of decades. If that happens, Obama will bear his portion of the blame (which is no greater than Bush’s).

The second and more fundamental problem is the continuing erosion of the middle class. But the frightening truth is that this is not the kind of thing that presidents control. I suspect that future historians will remind us how little power politicians have over basic economic conditions. Even if he wanted to, Obama couldn’t bring back the remarkable situation that existed between about 1945 and 1965, when human labor was less easily replaced by machines and the United States had no serious competitors in many industries.

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

Significantly restrict the drone program, if not end it altogether.

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

The Affordable Care Act, for better or worse. If it works (and it’s too soon to tell), it will be the most significant extension of the welfare state in half a century. If it doesn’t, it will be the last nail in the coffin of the Great Society, discrediting any major social programs in the future.

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

Impossible to say. Flip a coin.

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

Although he benefits from comparison to George W. Bush, I have found most of Obama’s speeches to be windy and dull. Unlike real masters of political rhetoric, such as Lincoln or Reagan, Obama is best when talking about himself. In that sense, the eloquent �race speech� of 2008 has the best chance of surviving.

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

Almost certainly. Like JFK, Obama’s appeal is mostly about who he is rather than what he’s done. But images are important too. For all his shortcomings, Obama reminds us of the changes for the better that America has made in the last 50 years.