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?

Twenty years from now, the fact that President Barack Obama was black will be what most Americans, no matter what their race, will think of first when he is mentioned in the national conversation. Twenty years from now, he will be the president first invoked whenever Americans talk about or allege the continuing existence or gradual disappearance of the great racial divide that has been a major aspect of American history and society from the start. And most interestingly, his name and his presidency will be used by those on both sides of that divide as proof of their argument as to whether we still have a long way to go or we’ve finally arrived as a society when it comes to figuring out the answer to the race question in America.

The fact that he was the first black elected as president will always be the most astonishing thing about his presidency to most Americans of all races 20 years from now. The fact that he exposed the deep racial and cultural divisions in America through the two coalitions he forged to win his two presidential campaigns will be seen as his major achievement as a presidential politician and electoral strategist. It will be interesting to see what the fractious Republican coalition he brought into oppositional being, made up of tea-party insurgents, birthers, the religious right, gun nuts, anti–Common Core home schoolers, fiscal conservatives, deficit hawks, and the pro-business wing of the party will look like in 20 years. It will perhaps be even more interesting to see how historians assess just how much the Republicans mattered and what they in fact contributed to American history and society during the Obama years.

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 will likely get a pass from most historians, only because 20 years from now, it will be far more easy to see that the deep racial and cultural divisions he exposed by his election as president two times made it impossible to expect or achieve any meaningful legislative compromises with the Republican coalition his presidency drove to distraction at times. Twenty years from now, historians will write that in reaction to his presidency, the Republican Party perfected the art of dog-whistle politics in making itself the safe haven for disaffected, downwardly mobile whites deeply disturbed by all the different racialized meanings they gave to Obama’s election as president and what it said about their former privileged and secured middle-class status within American society.

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?

With the recent events in Ferguson, like the events surrounding Trayvon Martin’s shooting death in Florida, President Obama was forced to speak to pressing issues of perceived racial injustice perpetuated by the American legal system against blacks and other minorities. It is during these most intense and racially charged moments that Obama seems to understand that he must reluctantly interject himself as a black man and a black president into the American conversation on race. It is in those moments that we begin to sense that the thing we least understand about Obama is how Obama sees himself as a black man; not only that, as a black man who became the first black president. His latest comments on being mistaken for a car valet and a waiter seem to suggest he has become more comfortable in letting blacks and other minority groups, and whites as well, in America know that not only does he understand racism. He himself has experienced racism and has felt the pain. That the president has more freely offered what Malcolm X famously called his own “racial perspective” on being a person of color in American society may give historians in the future insight and perspective into an aspect of his own personality and his presidency that is least understood right now.

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’d sure like to know what happens with the November election in 2016 before answering that question. Can someone like Hillary Clinton or Elizabeth Warren or Corey Booker, or even Joe Biden, reassemble the Obama coalition, with some gilding along the edges, and win the presidential election? It may be, 20 years from now, that the 2014 congressional electoral blowout for the Democrats will be seen as a far more significant event in assessing Obama’s legacy than we might think right now. How the Democrats react to that election over the next two years, who they nominate for president, and the way they think they can put an electoral-victory map together will tell us much of what we need to know about the longevity, durability, and portability of the Obama coalition.

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 answer that question with two years left to go in Obama’s presidency, at which point the books are closed, so to speak. With all the uncertainty, anxiety, and conflicting views among the American people, particularly among working-class families, of where the economy is headed in the short term and the long term, future historians will likely look at where the economy was when Obama took it over from Bush and the Republicans in 1988 and where it ultimately ended up 2016. Right now, things are just too up in the air to tell what the judgment will be on the Obama economy, 2008–16.

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 could use his last State of the Union speech in January 2016 to map out his vision, told from his perspective as the first black president, on where we stand on the issue of race heading into the last year of his presidency, and the work that needs to be done over the next 20 years.

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

As the first black elected as president, he got a national-health-care bill passed over the fierce opposition of the Republicans and paid for it the rest of his presidency.

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

It’s pretty low right now, even among some Democrats, so his reputation has a pretty good chance of improving from bad to about what you’d expect in his handling of, without question, the toughest job any black man ever had in the history of the entire country.

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

To me, it will be seen as the keynote speech he delivered at the 2004 Democratic National Convention. It put him front and center on a national stage, and forever cemented the first impression of Obama as being very eloquent for a black man in the minds of white Americans, a key to his successful run for president four years later.

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

Yes, as Kennedy’s image is tied to the myth of the White House as Camelot during his presidency, with little reflection on what that meant as a matter of consequence for the nation, Obama’s image will always be tied to being the first black president, with little reflection on what that meant as a matter of consequence for the nation as well.

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

Hillary Clinton of course, assuming that 20 years from now, her presidency ended in 2024. If not, I’d go for Eric Holder, as much as anyone in his administration, Holder maintained a consistent focus on racial justice as central to his department’s mission.

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

Military drones. They will be emblematic of Obama’s colossal failure as president to make the country squarely confront or even really stop to think about what it meant to construct the 21st-century surveillance state along the identical patterns that had been laid out by his predecessor, President George W. Bush.

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

Given that I have sought assess his presidency through the historical lens of critical race theory, I will cite an image laden with racial irony and symbolism. Obama, addressing the nation in the wake of the grand jury’s refusal to issue an indictment against police officer Darren Wilson in the shooting death of Michael Brown and calling for calm, while the split-screen TV image of rioters burning and looting in Ferguson was carried simultaneously on the news. The juxtaposition will come to symbolize the fact that not even our first black president could come up with an adequate response to the still-vexing problems of race in America.