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Obama and Trump: The ticktock of a truly bizarre relationship

From riding together up Pennsylvania Avenue to Trump accusing Obama of wire-tapping him, here's a look at their rapport since Trump's election. (Video: The Washington Post)

President Trump spent years questioning Barack Obama's birthplace and his legitimacy as president. On Saturday, Trump accused Obama of his own “Nixon/Watergate” scandal involving the wiretapping of Trump's phones.

In the middle of it all, though, Trump made an equally outlandish claim about Obama: That Obama actually likes him. “I don’t know if he’ll admit this, but he likes me,” Trump said a week after his inauguration. “I like him.”

Trump sure has a funny way of showing it.

And really, the relationship between these two men could fill a book — especially on Trump's end. From its earliest days, Trump seems to have been torn between respect for Obama and a desire to accuse him of high crimes using dubious information. Obama's posture toward Trump, meanwhile, has been steadier — a kind of diplomatic tolerance, with the occasional jabs (when he deemed them to be appropriate).

Here's a quick timeline:

Early skepticism

December 2006 — In an interview with Maureen Dowd, Trump offers his some of his first comments about Obama. And they are characteristically hot and cold, referencing Obama's relationship with Chicago real estate developer Tony Rezko:

He deems it ''not a good sign'' that Barack Obama got into a sketchy real estate deal with a sleazy Chicago political figure. ''But he's got some wonderful qualities,'' Mr. Trump says, and deserves another chance.

March 2007 — Trump: “Well, he's a star. I mean, he's really, really done an amazing job in a very short amount of time. The question is experience." (CNN)

January 2008 — Trump: “I certainly think he is a very capable guy and a great speaker. I was watching one of his speeches, and it was absolutely terrific. I think he's inexperienced at this point, but we will see what happens." (Fox News)

February 2008 — In some of his first comments about Trump at an event in San Antonio, Obama cites Trump's bankruptcies as something rich people can do.

“You can modify [your mortgage] on your second home or your third home,” Obama says. “So if Donald Trump decides he wants to file for bankruptcy and he wants to refinance, you know, his various houses and various vacation spots, he can do that.” But, Obama notes, less-wealthy people don't have this luxury.

September 2008 — Trump endorses John McCain over Obama: “This is not the right time for tax increases and Obama wants to increase your taxes drastically. So this is not … the right time.”

Trump also suggests Obama would have been better off picking Hillary Clinton as his vice president: “The fact is that Obama went limping across the finish line. He should have chosen Hillary. It would have been a much different race, I believe. Right now, it looks to me like McCain is probably winning." (CNN)

High praise for the new president

December 2008 — Trump: “I think he's doing great. I think Hillary is a great [secretary of state] appointment. I think that some of the others are just great appointments. … You watch. So I think he's doing a great job." (CNN)

Trump: “I think it's great. … A lot of people ask me, was the stimulus necessary? I think we would probably be in the Great Depression No. 2, which we probably are already. If they did in 1929 what they're doing now, you probably wouldn't have had a depression." (Fox)

January 2009 — Trump: “I really believe that Obama will be a great president, and I hope he is." (Fox)

February 2009 — Trump praises Obama's first news conference: “First of all, I thought he did a great job tonight. I thought he was strong and smart, and it looks like we have somebody that knows what he is doing finally in office, and he did inherit a tremendous problem. He really stepped into a mess.”

The pivot

Late February 2009 — Trump pivots on his stimulus praise and suggests Obama is spending too much on it and health care: “Well, absolutely. I mean, we're talking about numbers that are staggering. Your grandchildren and my grandchildren. I just had a grandchild two days ago. A lot of people are going to be paying. … But I just think that maybe we're at a point where instead of spending all this money, we should save money. We should maybe go with tax decreases." (Fox)

April 2009 — Trump: “I'm not saying I agree with everything he's doing. I do agree with what they're doing with the banks. … Beyond that, I'm not so sure I agree with it, because I — I am worried, ultimately, about inflation." (CNN)

BUT, Trump says Obama's first three months as president earn him a B-plus or better: “He's working very, very hard on many, many fronts. It would be nice if he could focus on one, but he wasn't really given that option." (CBS News)

March 2010 — Trump isn't sure about Obamacare: “I'm really torn. Number one, as a human being, I like to see people — it's inconceivable that you know people are sick, like you or I get sick or the kids get sick and you bring them to a doctor — inconceivable that you know 31 million people can't do that. … On another level, it's really going to cost a lot of money in terms of competitiveness with this country." (CNN)

September 2010 — Trump hits Obama's policy on taxing the rich: “They don't have to give money to the United States and to Mr. Obama where he wants to tax the hell out of everyone. I mean it's really getting to be a problem and a lot of people are thinking about leaving. A lot of the very, very rich that don't have maybe the same loyalty. If I left, that would be a problem. Do we agree? Would that be a story?" (Fox)

The birther campaign

March 2011 — Trump brings the birther movement to the mainstream on “The View”: “I want him to show his birth certificate. … There's something on that birth certificate that he doesn't like.”

April 2011 — Obama provides his long-form birth certificate showing he was born in Hawaii. Though he doesn't mention Trump by name, he clearly alludes to him as part of the “sideshows and carnival barkers” infecting American politics. Trump responds that he's “very proud of myself” for getting Obama to release the birth certificate.

Days later, at the White House Correspondents' Association dinner, Obama needles Trump with Trump sitting in the audience looking unamused. “I know that he's taken some flak lately,” Obama says. “But no one is happier, no one is prouder to put this birth certificate issue to rest, and that's because he can finally get back to focusing on the issues that matter, like did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?” Obama also makes fun of how gaudy the White House decorations would be if Trump were ever president, and mocks Trump for appearing with D-list celebrities like Gary Busey on “Celebrity Apprentice.”

August 2012 — Trump tweets the theory:

October 2012 — Trump offers Obama a $5 million donation for his passport and college records.

Obama engages him with humor again, joking on the “Tonight Show” that it's a rivalry that dates back to when the two of them were growing up in Kenya.

Public enemies Nos. 1 and 2

November 2015 — Trump calls Obama “a threat to our country.”

June 2016 — Trump seems to call into question Obama's loyalty to the United States. “You know, people cannot believe that President Obama is acting the way he acts and can't even mention the words radical Islamic terrorism,” he says on Fox News. “There's something going on. It's inconceivable. There's something going on.”

August 2016 — Trump says Obama is “the worst president maybe in the history of our country.” He would later call Obama a “founder of ISIS” at a campaign rally.

Nov. 6, 2016 — On the eve of the election, Obama says Trump can't be trusted with the nuclear codes. “Over the weekend, his campaign took away his Twitter account,” Obama says. “Now, if your closest advisers don't trust you to tweet, then how can we trust him with the nuclear codes?”

President Obama campaigned for Democratic presidential nominee Hillary Clinton in Kissemmee, Fla. (Video: The Washington Post)

The brief bromance

Nov. 11, 2016 — After a joint meeting the Oval Office, Trump says Obama is “a very good man” and that the two of them have good “chemistry.” Obama tells Trump, “If you succeed, the country succeeds.” Trump says, “Mr. President, it was a great honor being with you, and I look forward to being with you many, many more times.”

Dec. 7, 2016 — Trump says he likes Obama: “I must tell you, you know, I never met him before this. I never spoke to him before this. I really — I do like him.”

Bromance off

Dec. 28, 2016 — Trump tweets that Obama is undermining his transition effort.

… And quickly back on

Later Dec. 28, 2016 — But Trump then seems to back off: “I'm getting along very well with him, other than a couple of statements that I responded to and we talked about it and smiled about it. And nobody is ever going to know because we're never going to be going against each other in that way.”

Feb. 6, 2017 — Trump tells Bill O'Reilly that Obama likes him:

TRUMP: It’s a very strange phenomenon. We get along, I don’t know if he’ll admit this, but he likes me. I like him —
O’REILLY: How do you know he does?
TRUMP: Because I can feel it. That’s what I do in life, it’s called — like, I understand.

… And off again

Feb. 27, 2017 — In a Fox News interview, Trump accuses Obama of fomenting protests against him. “I think he is behind it. I also think it is politics, that's the way it is.”

March 4, 2017 — Trump accuses Obama, without any evidence, of personally wiretapping his phones.