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?

Two decades after Obama’s presidency, historians will still be battling over it, and the fiercest arguments may not be between the right and the left, but among left/liberal scholars. I expect that progressive historians will divide between sympathetic scholars who believe that the promise of a more transformative presidency was thwarted by the era’s extreme partisanship, and historians who are critical of Obama’s militarism and National Security Agency surveillance. Historians will be sensitive to the problems Obama inherited, so they will credit him for keeping the economy from a deeper and more devastating dive. Overall, it will be seen as an era of weaker presidential power in the domestic arena, in spite of the Affordable Care Act, with Obama repeatedly in deadlocked negotiations with Republican leaders, and the president unable to build on the outpouring of emotion following the Sandy Hook shootings to move the country forward on firearm regulation. Although Obama inherited the war on terrorism, historians will see him as having built upon the past policies, rather than ratcheting them back, perpetuating and legitimating targeted killing, widespread surveillance, and secrecy.

Race will still matter. Twenty years from now, children will learn in school that Barack Obama was the first nonwhite U.S. president. Some will see Obama’s presidency as showing that the early-21st century was a moment of progress, in spite of continuing racial inequality and uproar over police killings of unarmed people of color. But civil-rights historians are likely to view Obama’s legacy on race to have been undermined by the record number of deportations, the impact of immigration policy on Latino and Asian communities, and the fact that the president did not issue an executive order on this until the middle of his second term.

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, because its continuation not only undermines the U.S. global image but also is a powerful reminder of a broken promise, suggesting weak presidential leadership.

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

Tie between killing Osama bin Laden and the advancement of LBGT rights in the areas of marriage and military service.

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

Improved: The political atmosphere right now is so toxic that there is no way to go except up.

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

His first inaugural address.

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

The sleeper for the category may be Attorney General Eric Holder because legal developments—from LGBT equality to internal legal opinions about targeted killing, surveillance, and secrecy—are likely to have staying power.

(Although not cabinet or staff, a crucial member of Obama’s circle has been First Lady Michelle Obama, whose positive public image reinforces the important symbolic impact of Obama’s presidency. Many First Ladies are forgotten in history; Michelle Obama will be remembered.)

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

Most significant because most enduring will be the way Obama has legitimated and institutionalized the use of drones, including for targeted killings, developing a secret set of rules about their use.

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

Nothing matches the powerful image of Obama’s first inauguration, as hundreds of thousands flocked to Washington.