With the caveat that his administration is not yet finished, and two years is a long time, how will history judge Obama?

Why has Obama disappointed? In part, it is because of partisanship, his conservative opposition constantly obstructing and opposing because it played well to broad reaches of the electorate. But part is also his personal failing. He turns out to have not been the politician some had hoped; he did not rise to the occasion like a Roosevelt or a Johnson. He was no master in the grit of Washington politics but seemed to withdraw from the fight and the messiness of the negotiation, dealing, and cajoling necessary to win an agenda. He seemed too intellectual, always preferring the high road and eschewing the trenches. He seemed too nice a guy, which only whetted the appetites of his opposition. Their strategy was to wear him down, and it largely succeeded. And thus, Obama will leave little legacy regarding the operation of the office he held and the party position he was to command. He might be regarded ultimately as a sort of Woodrow Wilson, a good-intentioned president, cerebral and moral, but a failure as a politician.

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’?

China policy may turn out to be his greatest foreign-policy failure, next to the Middle East. Obama had the opportunity to forge a closer, more collaborative relationship with Beijing but failed to do so. Beijing had been interested. China’s leaders and Obama spoke encouragingly of a “new great-power relationship” in which the two seemed to acknowledge the vital importance of working closely together to solve common problems and address conflicts in prudent ways. But in practice, the relationship has seriously soured. The mood is dark, and both sides now seem to be seeking new ways to out-circle the other. The future appears to be bleak, with relations even further deteriorating.

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 should make sure that he aggressively opposes attacks on health-care reform and ensures that Congress does not gut Obamacare. He can do this and ensure that critical achievement of his presidency.

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

Health-care reform. If he can defend it.

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

His reputation will improve in 20 years. I fear worst things are to come to the country which will make these years look better.

Which of Obama’s speeches and phrases will be the most enduring?

His speeches on race and on the need to end war—all wars must come to an end—we will remember his eloquence.

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

Orator. He will be judged to have been a terrible administrator.

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

The negative shadow over Obama will long endure and obscure his accomplishments. Obama was positively compared to JFK during his first campaign, but he has fallen far short of the JFK myth.

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

Hillary.

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 ground troops should be commended but the increase of drones is directly connected. Americans don’t want further combat deaths but neither do they want to endorse the difficult but necessary effort to construct a new foreign-policy attitude that addresses the real grievances against the United States around the world.

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

Lasting symbolic image of the Obama presidency: he with his beautiful family onstage in victory night No. 1.