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?

Race will matter as a historic first much the same way that Kennedy is remembered as the first Catholic president, as groundbreaking in a symbolic way. Obama’s ascendancy to the presidency will stand as a marker of the transformation of American attitudes about race that have resulted from the civil-rights movement. This will figure as a very significant aspect of his presidency.

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 presidency may be seen as a historic missed opportunity—a moment much like FDR’s, when a strong leader and a galvanized base utilized an economic crisis to reshape and reorient public policy. The New Deal was transformative because of this combination of factors. Barack Obama’s presidency has not been in the same way. No doubt, historians will recognize the Republican opposition to blocking what he was able to accomplish. They will also ask if a more powerful leadership style could have overcome that opposition by further galvanizing the liberal-progressive energized base that brought him to office.

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 Affordable Care and Patient Protection Act (Obamacare). Despite its limits and compromises, the ACPPA was nonetheless a breakthrough public policy. By acknowledging a government obligation to ensure that Americans (not just the elderly and the poor) have access to health-insurance coverage, it has ensured a new stake in the political process for millions who now receive government-subsidized coverage on health exchanges. This is why it has proved such a bone of contention among conservative Republicans. If the problems with the current system along with increased pressure on employer-provided plans lead to calls for the expansion of government-provided health care, rather than its retrenchment, the ACPPA may stand as the first step toward the U.S. embrace of a single-payer health-care system.

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 will be judged as a somewhat lackluster performance. The economic crisis that Obama inherited offered an opportunity to rein in the power and excess regulatory freedom of banking and business interests that had gotten the nation into the crisis in the first place. Obama’s reliance on economic advisers such as Larry Summers, with close ties to Wall Street, shaped the limits of the changes he was willing to back.

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

Close Guantánamo.

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

Affordable Health Care and Patient Protection Act

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

I think it will improve.

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

His March 2008 speech in response to comments by Pastor Jeremiah Wright when Obama called for a more perfect union. The speech was notable for his effort to reference Lincoln’s rhetoric and his legacy. It will stand as the most powerful statement Obama made on racial injustice and a testament to his core vision and beliefs. Obama hoped to build on America’s still unfinished Second Reconstruction to bring freedom, equality and prosperity for all Americans. The speech reveals the personal (and somewhat optimistic) vision of himself as a “great conciliator” between white and black segments of the nation and the linkage of that vision to his own personal experience.

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

Orator.

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

Kennedy’s overall domestic accomplishments were limited due to his preoccupation with the Cold War—his image for that reason outshone his actual achievements. This will likely be the case with Obama as well. His historic legacy as the first black president will be more important than his concrete and limited legislative achievements.

During his presidency, at key moments, Obama has chimed in on the ongoing problem of racial injustice. At the same time, under his watch, ironically, historic rates of inequality between rich and poor continue to spike, African-Americans are incarcerated in highly disproportionate numbers, and relations between police and black communities are deeply fraying. Should a large-scale movement to end mass incarceration, improve police and community legacies, and rein in rising historic rates of inequality emerge in the wake of his presidency, perhaps his presidency may be remembered as a way-station toward that movement.

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

The increase in military drones.