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A brief look at Donald Trump and Dennis Rodman's history, from being fired on 'The Celebrity Apprentice' to dealing with North Korea's Kim Jong Un

Suzy Byrne
Editor, Yahoo Entertainment
Donald Trump’s presidential reality show continues with a cameo from Dennis Rodman. (Photo: Getty Images)

We’ve seen many incarnations of Dennis Rodman through the years, but Weeping Dennis Rodman — done with joy over the Donald Trump and Kim Jong Un summit — was a new one.

Rodman — who was in Singapore for the summit, but playing no official role, according to the White House — has long been making headlines about his bizarre friendship with the North Korean dictator. He’s talked about how the basketball-loving politico is his “friend for life” and loves karaoke, TV theme songs, and table tennis. But what about Rodman and Trump? Well, they go back some time as well.

Did you meet Weeping Dennis Rodman? Here he is:


The former NBA star was proudly rocking his MAGA hat during his CNN interview on Monday, but he’s had an up-and-down relationship with Trump through the years. Case in point? Season 8 of The Celebrity Apprentice, in 2009, when the Donald confronted the Worm over his drinking — and fired him for his erratic behavior.

You’re fired, Dennis — Round 1:

But dramatic firings — and Rodman freakouts — made for great TV, so naturally Trump brought back Rodman for the all-star edition in 2013. How did that go? Well, he promptly fired him again. That time it was for — horror of horrors — misspelling future first lady Melania Trump’s name on an ad campaign. He was the project manager, so the buck stopped with him — and he got to hear Trump’s two-word catchphrase again.

You’re fired, Dennis — Round 2

On social media, their back and forth has been both nasty and nice. When Rodman endorsed him as presidential material in 2015, it was, of course, pleasant.


But we wouldn’t exactly say “Crazy Dennis Rodman” is a term of endearment.


Or that “delusional” is very nice. Here, Trump said that he was glad to fire Rodman twice, who has long been trying to get the U.S. and North Korea on better terms.


Though Trump has never been above using Rodman for self-promotion.


Or using him to diss President Obama.


So is it so crazy that Rodman played a part in bringing together Trump and the controversial North Korean leader? Not really. Trump  said in 2013 that he thought it was good that Rodman was the unofficial U.S. ambassador to North Korea.

Trump thought Rodman was doing good work with North Korea in 2013:

“Well, it’s probably better than what we have,” Trump said on Fox News. “If you look around, the world is blowing up around us. Maybe Dennis is a lot better than what we have.” He said that what Rodman was doing “it’s not an act.” He talked about “how sharp and smart” Rodman was on The Celebrity Apprentice.  Despite firing him twice, he said, “Dennis is not a stupid guy. Dennis is smart in many ways,” especially — “streetwise.”

All this said, it’s not like Worm will be spending Thanksgiving at Mar-a-Lago with the Trump gang. Last year, Rodman said he hadn’t seen him since The Celebrity Apprentice ended four years earlier. In this interview, Rodman described “Trump” as someone who “loves power” and loves “to talk s***.”

Rodman and Trump hadn’t seen each other in years:

But according to Rodman, it’s all warm fuzzies between them now. On CNN Monday, he said he received a call from the White House — ahead of the summit — and was told that Trump was “proud” of him and that Trump “thanks him a lot.”

Though there is no bigger hero in Trump’s mind than himself, as depicted in this odd trailer the White House made recapping his meeting with Kim:


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