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?

The election of Barack Obama as the nation’s first black president will still matter but not in ways that we might assume. Our society crossed a symbolic threshold, but the shallow assumption that Obama’s presidency proves that the U.S. is now a post-racial society is discredited on a daily basis.

Obama’s rise agitated and troubled a racial landscape that many thought appropriately tranquilized. Thanks to affirmative action and the normalization of values of diversity within elite institutions, the country has more racial and gender inclusivity at the top than perhaps at any other time in its history. At the same time, a racially disparate criminal-punishment system will, under current trends, lock up one in three black men during the course of his lifetime.

This was always combustible stuff. The post-civil-rights racial order is coming undone�on Obama’s watch. The contradiction Obama embodies��one black man in the White House, 1 million black men in the big house��has something to do with this. Not only has Obama’s rise stirred a barely concealed racism�integral to the preservation of white supremacy at local scales, and to the constitution of one of two major national political parties�he also raised expectations of leftists, liberals, and progressives that have been bitterly disappointed.

Some may forgive Obama for his failings on matters of racial justice, perhaps understandably so, given what he represents. Nonetheless, Obama lost whatever importance he may have had as someone capable of moving the nation beyond the rifts of race.

That is ultimately a good thing. Because as much as symbolic thresholds matter�at lower frequencies where people live�the old race and class problems of structural inequality, normalized stigma, and everyday brutalization, especially at the hands of police, persist. Mass protest against the impunity with which black men and women from Tarika Wilson and Trayvon Martin to Michael Brown and Eric Garner have been killed recently, are bringing the contradictions of the post-civil-rights era to a head. Obama does not deserve credit for this, but he is a symptom.

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)?

Obama’s is not the transformative presidency that many hoped it would be. While Republican obstructionism will be regarded dimly in future, as now, a lack of boldness and an aversion to risk on the part of the Obama administration (for example, when the bankers and traders were one their knees) is likely to be seen as part of an overall culture of mendacity, cronyism, and pay-to-play that grips our nation’s capitol.

It maybe correct to see the Reagan presidency as transformative, though not for ending the Cold War�which had more to do with internal Soviet dynamics and the rise of Gorbachev. But Reagan did restore a kind of innocence to the use of U.S. violence in the world (helping to create the Guatemalan killing fields and the Afghan mujaheddin, among other things, in the process). And Reagan engaged state power at home (especially against organized labor and the urban poor) in ways that unbalanced the field of class relations, promoting a trajectory of widening and deepening economic inequality on which we remain.

As important, the Democratic Party long ago joined the great moving-right show. In the guise of greater reasonableness, even fairness, Democrats have advanced and legitimated significant right-wing policy successes of our time. Just as Clinton cemented the war on crime and �ended welfare as we know it,� Obama has largely entrenched, in the name of restraining, the so-called war on terror.

Democrats distinguish themselves on important social questions�gender equality, racial inclusion, tolerance for diverse sexualities�but not in ways that hinder or challenge the prerogatives of big-corporate or �deep state� (i.e., national-security) interests and constituencies. The Obama administration was presented with tremendous opportunities to begin to shift the terms of center-right commonsense and public policy�on war, militarism, and economic fairness. The modest achievement of the Affordable Care Act notwithstanding�it has decidedly failed to do so.

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?

I was struck by a passage from Dreams From My Father written by the pre-presidential Obama, after 9/11. The conflict between �worlds of plenty and worlds of want,� he writes, �twists the lives of children on the streets of Jakarta or Nairobi in much the same way as it does the lives of the children on the South Side of Chicago.� Failing to understand this, the powerful needlessly intensify a destructive spiral with their �dull complacency � unthinking applications of force � longer prison sentences and more sophisticated military hardware.�

Obama’s subsequent policy and vision has not only failed to rise to the level of his own insights into the inadequacy of American military and police power as the leading edge of government in a world plagued by fear and want; it has run in the opposite direction. From assassination by drone (accompanied by more unseemly �lawfare��the �drone memos�), to sustaining and augmenting an inhumane deportation regime, surpassing 2 million persons and counting, to the crackdown on whistleblowers and press freedoms, to the funneling of �excess� U.S. military hardware into local police departments, the militarization and overpolicing of American life proceeds apace.

At the same time, Obama has quietly but importantly attempted to lower the volume on the ongoing wars on terror, drugs, and nonlegal migrants, perhaps in the hopes that they might begin to lose steam and even pass from the scene. Eric Holder’s push for sentencing reforms for low-level drug offenders and Obama’s recent executive action on behalf of a select number of illegal immigrants are examples. That such actions are invariably accompanied by calls to strengthen enforcement bureaucracies means that in the final analysis, they are inconclusive and tend to run counter to reform over the longer term.

Obama also put the leash back on overt U.S. military action just as it approached its breaking point under George W. Bush. That he did so in the interests of relegitimation rather than transformation (for example, releasing the torture memos but failing to prosecute the torturers) sets us up for an uncertain future or, worse, a new round of dirty wars. But this ambivalence might be regarded as a kind of achievement�one that is not always understood by an analysis that sees Obama’s national-security approach as simply an extension of Bush-Cheney.

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?

Obama has continued the escalation of executive power that has been characteristic of the �imperial presidency� in the post-WWII era in ways that have pleased and displeased both left and right. (For example, see aforementioned actions on whistleblowers and immigration or the more recent landmark agreement with China to establish carbon-emissions reduction targets.) But the Obama administration has done nothing to shift the balance back to Congress when it comes to the key issue of authorizations to use military force. Executive authority continues to reign supreme in the nation’s seemingly endless appetite for �small wars.� If executive action is hamstrung when it comes to creating valuable and enabling social policy for the mass of Americans, in the department of mass destruction by weapons, it continues to reign more or less unchecked.

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’?

Reducing U.S. force in Iraq was necessary; the rapid scaling down of the U.S. military presence there will be judged positively in the long run. Given the horrors of Abu Ghraib and Fallujah (only the half of which we really know), the seeds of enmity in the region, however, are now deeply sewn. (A recent report, for example, suggests that 17 of 25 of ISIL’s top leaders spent time in U.S. prisons in Iraq between 2004 and 2011). Though Obama may understand the perils of blowback better than his predecessor, his failure to end the war in Afghanistan will haunt his legacy, with the cost of this war now estimated at $1 trillion, 80 percent of which has been spent during his tenure. By the same token, the recent climate treaty negotiated with China, and the proposal to normalize diplomatic relations with Cuba, are salutary. Both are important milestones, if long overdue.

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?

There has been no �Obama realignment� around �millennials, minorities, and women��as a durable or even coherent liberal-progressive voting bloc of the future. Although the Republican Party as currently constituted will be hard-pressed to win national elections, the gerrymandered congressional map looks likely to guarantee a sclerotic, right-leaning Congress for some time. Efforts at voter suppression, and to remove any remaining strictures on big money in politics, proceed and threaten to rob us of our democracy, such that it is, permanently. In the absence of significant countervailing, large-scale, organized movement from below and from outside the current political Establishment in the interest of gaining equal access to, and wider, fairer distribution of governmental power and resources, the prospects of U.S. institutional politics are not bright.

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?

No. Nothing has been saved. We currently subsist in a low-growth, high-unemployment, stationary state with the next, maybe bigger economic crisis looming. In U.S. society, those at the top are actively insulated from risk, while increasing precariousness is delivered to those at the bottom and in the middle. The recent example of the big banks inserting legislation into the budget bill to allow them to once again engage in certain types of high-risk trading with government-insured savings deposits is an indicator of business as usual and our continuing, collective economic peril.

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

Pardon Edward Snowden! Such executive action would acknowledge the dangers that the homeland-terror-surveillance state poses to a democratic way of life�even more so than Eisenhower’s belated, if oft-cited, warnings about the rise of the military-industrial complex more than half a century ago.

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

His breakthrough as the nation’s first black president.

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

Improved. Obama is a better president under more difficult circumstances than his four predecessors. I believe this is the appropriate comparison. That said: The bar was set very low.

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

The famous race speech during the election remains a landmark and for all its equivocation proof of Obama’s substantial intellectual and political gifts.

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

Orator, but therein lies the problem �

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

There will be no Obama myth. We know too much.

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

Valerie Jarrett, chief insulator and purveyor of �boardroom liberalism.�

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

Drones. The arrogation of the right of the U.S. president to kill anyone, anywhere in the world, without due process is an abomination and suggests a government that still regards itself as above and beyond the law: the definition of a rogue state. Moreover, detailed on-the-ground analysis by the human-rights group Reprieve points out that U.S. attempts to kill 41 individuals in drone attacks have resulted in over 1,100 deaths. Even if assassination by drone were acceptable, these numbers (or anything approaching them) suggest a level of operational failure, a lack of accountability, and a sheer disregard for human life that should not be.

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

This is subjective, but I’ll never forget the eerie photograph from the stage in Grant Park in Chicago with the Obamas and Bidens happily celebrating their 2008 electoral victory from behind a barely visible sheen of bulletproof glass. In retrospect, this image foreshadowed three things: Obama’s ultimate remove from the populist hopes he inspired, the racially defined threat inflation he stoked on the right, and shadowy infrastructures of security he has innovated and entrenched.