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?

Like his predecessor, President Obama has used executive orders to implement domestic programs that Congress refused to enact. Just as George W. Bush pledged to enact “charitable choice” programs despite Congress’s intransigence, so Obama has used executive orders unilaterally to raise the minimum wage and to enact immigration reform. In terms of numbers, Obama’s bark is worse than his bite: He issued 168 executive orders in his first term, compared to Bush’s 173 and Clinton’s 200. Nevertheless, Obama’s rhetoric on executive orders has been so polarizing—“Where I can act without Congress, I’m going to do so.”—that he has inflamed his opponents and strengthened their resolve to reverse his achievements. Just as the Supreme Court unanimously rejected Obama’s efforts to use recess appointments, so it could reject his immigration orders. Throughout history, unilateral presidential actions designed to circumvent Congress have led to pushback in the Courts and Congress that have ultimately undermined, rather than strengthened, the president’s legitimacy.

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

Appoint transformative judges to the lower courts.

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

His two Supreme Court appointments.

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

Improved.

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

His race speech at the National Constitution Center.

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?

No.

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

Kathy Ruemmler.

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

Drones.

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

His speech on Election Day, 2008.