The Last 100 Days: Obama’s Biggest Mistake edition

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Ever since the administration of Franklin Delano Roosevelt, presidents have been judged on the successes they notch during their first 100 days. Now, as Barack Obama prepares to end his historic turn on the political stage, Yahoo News is running The Last 100 Days, a look at what Obama achieved during his consequential presidency, how he navigates the struggles of his last months in office and what lies ahead for him after eight years filled with firsts. We will also look at how the country bids farewell to its first African-American president.

It’s not a literal 100 days — Obama leaves office in late January 2017.

And it won’t all be about policy. As Obama himself is fond of noting, he also spent his two terms as father to daughters Malia and Sasha and husband to first lady Michelle Obama. And even without much input from the White House, the cultural landscape shifted dramatically over his two terms on issues such as gay rights.

And then there’s the way the president sees the presidency — not just his tumultuous years at 1600 Pennsylvania Ave., but also the institution and its relationships (for better or worse) with other branches of government and with the news media.

In this 12th installment, we look at Obama’s answer to the classic question modern presidents frequently face: What was your biggest mistake?

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Being president of the United States provides immense power and almost limitless opportunities to screw up.

And commanders in chief do screw up in ways large and small, and the results can be devastating or merely annoying, historic or just the focus of an awkward news cycle.

Asking presidents to reflect on their biggest mistake can shed light on how they view the power, and the limits, of their office, or how they might approach a future problem that resembles the one they think they handled inadequately.

The question can also provide someone at the apex of American politics with the opportunity to deliver an insincere, self-serving answer, like the job seeker who makes a show of confessing in an interview that their biggest shortcoming is that, gosh, they are a perfectionist. It’s also important not to confuse “biggest mistake” with “biggest regret” — a mistake is something that should have been done differently, a regret might be something beyond even a president’s control.

George W. Bush infamously bungled John Dickerson’s question on the matter. Among the Bush press corps, it became known as “the Dickerson Question.”

At an April 13, 2004 press conference in the East Room of the White House, Dickerson, the Time magazine reporter who now hosts “Face The Nation” on CBS, stood up and asked then President George W. Bush this:

“In the last campaign, you were asked a question about the biggest mistake you’d made in your life, and you used to like to joke that it was trading Sammy Sosa. You’ve looked back before 9/11 for what mistakes might have been made. After 9/11, what would your biggest mistake be, would you say, and what lessons have you learned from it?”

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