In most Obama speeches that tell the story of American progress and how we have always worked to live up to the promise of our founding documents, he seems optimistic and confident that that history will continue. In Wednesday’s speech the question of whether America will get this right this time — at least in his view — seemed uncertain.

This is the same uncertainty Obama has been wrestling with since Trump was elected. According to one of his adviser’s memoirs, in late 2016 Obama’s confidence in his understanding of the American mood was shaken by Trump’s victory.

Since then, Democrats have regained a lot of political turf, mostly in 2018. But after Trump’s victory, Obama turned to his aides and asked a question that still hangs over the 2020 campaign.

“What,” he wondered, “if we were wrong?”