We typically think of Donald Trump and Barack Obama as bitter foes. After all, Trump was highly critical of Obama as president, and spent years spreading the baseless birther conspiracy in an attempt to undermine his legacy. Obama threw his own jabs at Trump in return, never dreaming the reality star would one day have his job!
However, when Trump won the presidency in 2016, he and Obama finally had to meet in person after years of barbs between them. And they reached a level of civility between them that you might not imagine was possible!
Trump and Obama even had long talks together about the country. At one point, Trump asked Obama what his biggest mistake as president was, possibly so that he could avoid such a mistake himself.
You’ll never guess how Obama responded! Here’s the full story.
Trump and Obama’s history of conflict
Donald Trump never actually met Barack Obama before winning the presidency and coming to the White House. And perhaps it was meeting Obama that made Trump feel he could ask the former president for advice.
Before this, though, Trump seemed to have nothing but disrespect for Obama. Trump’s biggest insult was that he basically breathed life into the Birther Movement. This was a conspiracy theory that said Obama was not born in the U.S. but in Kenya and, therefore, could not legally be president.
This movement built up enough steam that Obama released his actual birth certificate in 2011 to squash the rumors. Trump was not convinced and later offered to pay $5 million to Obama’s favorite charity if Obama would release a copy of his passport and college transcripts. (It should be noted that Trump later refused to share his own college transcripts as president.)
Obama took most of this in stride, but he wasn’t above striking back at Trump.
During the 2011 White House Correspondents’ Association Dinner in which Trump was in attendance, Obama said he would reveal his birth certificate and then showed a clip from The Lion King.
Later, Obama unveiled a mocking Photoshop of what a Trump White House would look like: a combination hotel, casino, and golf course covered in tacky gold.
Trump revealed he liked and respected Obama once he met him
Given this history, you may wonder why Trump would ask Obama for advice when he became president. What prompted Trump to suddenly turn to the man he had insulted and demeaned in order to gain some wisdom?
After Trump’s surprising win in 2016, it seemed both Trump and Obama wanted to put their bad blood aside to ensure a successful transition of power for the country.
Obama met with Trump on Nov. 10, 2016, after Trump had been declared President-elect. In the video above, Obama says, “My number-one priority in the coming two months is to try to facilitate a transition that ensures our President-elect is successful.”
Trump was similarly agreeable and even revealed he respected Obama. “We had never met each other. I have great respect…. Mr. President, it was a great honor being with you, and I look forward to being with you many, many more times in the future,” Trump said.
By December 2016, Trump revealed that he even really liked Obama as a person, which you can hear in the video above.
“I’ve now gotten to know President Obama. I really like him…. We have a really good chemistry together. We talk,” he told TODAY’s Matt Lauer. “He loves the country. He wants to do right by the country and for the country. And I will tell you, we obviously very much disagree on certain problems, on certain things. But I really like him as a person…. I never met him before this, but I really, I do like him.”
Trump also revealed that he asked Obama for advice when choosing members of his cabinet in 2016. “I have asked him what he would think of this one and that one. I take his recommendations very seriously.”
It’s worth noting that Trump has praised his foes before, including Hillary Clinton in an Oct. 2016 debate. “She doesn’t quit. She doesn’t give up. And I respect that,” he said.
Long story short? To Donald Trump, fighting someone with very dirty methods doesn’t mean that he can’t respect that person. And that is most likely what led him to honestly ask Obama about the biggest mistake he made as president.
Trump asked Obama what his biggest mistake was
So, when and why did Trump ask Obama what his biggest mistake was? We have the details about this particular interaction thanks to Bob Woodward and Robert Costa’s new book Peril, published in September 2021, which is mostly about the transition between the Trump and Biden presidencies.
However, the authors describe Trump and Obama riding together from the White House over to the Capitol for Trump’s inauguration on January 20, 2017. They revealed that Trump asked Obama a probing question.
With his typical bluntness, Trump turned to Obama and asked, “What was your biggest mistake?”
But Obama totally dodged Trump’s question. “I can’t think of anything,” he said.
It’s not immediately clear why Obama gave this response. It could have been lingering resentment that he had for Trump’s previous insults. Or it could have been simple pride, with Obama not wanting to admit weakness in front of a rival (something that Trump might even respect). Or it could even be that he really just couldn’t think of anything in that moment.
But one thing is clear: Obama effectively contradicted himself with this response. Because he had revealed what he thought his biggest mistake was in an interview months earlier!
Obama reveals his biggest mistake
According to Woodward and Costa, Trump posed that question to Obama in January 2017, where he claimed he couldn’t think of any mistakes. But months earlier, in April 2016, Obama had revealed his biggest mistake in a rare interview with Fox News.
During that interview, journalist Chris Wallace asked him point blank, “Worst mistake?”
Obama didn’t seem to have any problems coming up with an answer for Wallace.
“Probably failing to plan for the day after, what I think was the right thing to do, in intervening in Libya,” he said, referring to the fall of Libyan dictator Muammar Gaddafi.
Trump may not have been able to get out a truly reflective answer from Obama back in 2017. However, now that Trump is making noise about deciding whether to run for president in 2024, we have a feeling he won’t be asking Obama for advice ever again!