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People who know Barack Obama personally tell us that he is very self-confident and highly ambitious. But unlike others who claim those characteristics, one word that would not describe him is certain. Here is how James Kloppenberg described the former president:

The Obama who wrote Dreams and Audacity stands in a long tradition of American reform, wary of absolutes and universals, and committed to a Christian tradition that prizes humility and social service over dogmatic statements of unbending principle. A child of the philosophical pragmatists William James and John Dewey, Obama distrusts pat formulas and prefers experimentation…

After almost two years as president, Obama has failed to satisfy the left for the same reason that he has antagonized the right. He does not share their self-righteous certainty.

Obama affirmed that embrace of uncertainty during his commencement address at Notre Dame in 2009.

Remember, too, that the ultimate irony of faith is that it necessarily admits doubt…And this doubt should not push us away our faith. But it should humble us. It should temper our passions, cause us to be wary of too much self-righteousness. It should compel us to remain open and curious and eager to continue the spiritual and moral debate that began for so many of you within the walls of Notre Dame.

Those are the things that came to mind when I read the review of Ben Rhodes book, The World as It Is, by Peter Baker. The election of Donald Trump obviously sparked some doubt and curiosity from Obama.

Riding in a motorcade in Lima, Peru, shortly after the 2016 election, President Barack Obama was struggling to understand Donald J. Trump’s victory.

“What if we were wrong?” he asked aides riding with him in the armored presidential limousine.

He had read a column asserting that liberals had forgotten how important identity was to people and had promoted an empty cosmopolitan globalism that made many feel left behind. “Maybe we pushed too far,” Mr. Obama said. “Maybe people just want to fall back into their tribe.”

His aides reassured him that he still would have won had he been able to run for another term and that the next generation had more in common with him than with Mr. Trump. Mr. Obama, the first black man elected president, did not seem convinced. “Sometimes I wonder whether I was 10 or 20 years too early,” he said.

On that last question about whether he was 10 or 20 years too early, Dana Milbank answers in the affirmative.

Ten or 20 years from now, America will be much closer to the majority-minority nation it is forecast to become in 2045. A racist backlash to a black president wouldn’t matter as much.

But what was naively proclaimed in 2008 as post-racial America was instead kindling for white insecurity, and Trump cunningly exploited and stoked racial grievance with his subtle and overt nods to white nationalism. He is now leading the backlash to the Obama years and is seeking to extend white dominion as long as possible, with attempts to stem immigration, to suppress minority voting and to deter minority census participation.

Following Obama’s pattern, I’m not so certain that a racist backlash wouldn’t matter as much in 2045. Actually, where I part ways with Milbank is that it wasn’t just a black president who triggered that backlash. It was also the very demographics he refers to that played a role, perhaps even bigger than Obama himself. Here’s what white nationalist Richard Spencer said about that:

“Trump, on a gut level, kind of senses that this is about demographics, ultimately. We’re moving into a new America.” He said, “I don’t think Trump is a white nationalist,” but he did believe that Trump reflected “an unconscious vision that white people have – that their grandchildren might be a hated minority in their own country. I think that scares us. They probably aren’t able to articulate it. I think it’s there. I think that, to a great degree, explains the Trump phenomenon.”

Barack Obama knows that it is impossible to go back in time and delay his decision to run for president in 2008. It’s also impossible to know what might have happened if he hadn’t made that decision. A Hillary Clinton presidency? Might that have prompted an entirely different kind of backlash? For all we know, we could have been looking at eight of McCain followed by Palin running in 2016 instead of Trump.  In other words, things could actually be worse.

What Obama was doing by posing those questions was to prompt some creative thinking by asking the difficult questions—of himself as well as others. He was trying to understand how the unthinkable had happened. Here’s how Kloppenberg described that process:

“I am obligated to try to see the world through George Bush’s eyes, no matter how much I may disagree with him,” he wrote in Audacity. “That’s what empathy does—it calls us all to task, the conservative and the liberal … We are all shaken out of our complacency.” Obama rejects dogma, embraces uncertainty, and dismisses the fables that often pass for history among partisans on both sides who need heroes and villains, and who resist more-nuanced understandings of the past and the present.

There are those who read Baker’s review and saw this side of Obama as a sign of weakness. It is, in fact, the exact opposite. It takes an incredibly strong ego to ask those difficult questions at such a defining moment. I don’t think it’s ever too early for a leader like that.

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