The roast by Obama that insulted Trump so deeply it motivated him to run for president

After a decade of flip-flopping between a one-sided bromance and outright hostility, Mike Bedigan examines the history of Donald Trump's beef with the Obamas and the 'roast' that started it all

"You know who was nasty to me? Michelle Obama," Donald Trump told rally-goers in Georgia on October 28, to a chorus of boos and jeers. “She opened up a little bit of a box… That was a big mistake she made,” he added, ominously.

The former president went on to claim that he had “always tried to be so nice and respectful," towards the former First Lady, despite having spent years accusing her husband of secretly being born in Kenya and therefore ineligible to be a US president.

Trump had indeed once spoken highly of Barack Obama during the early stages of his presidency in 2008, calling him a “very capable guy and a great speaker.” He later said that the 44th president was doing a “great job” despite having inherited “a mess.”

Donald Trump has claimed he has ‘always tried to be nice and respectful’ to the Obamas, despite years of trashing the 44th president (Getty Images)

But an escalating beef between the two men began in 2011 when Trump began publicly espousing a birtherism conspiracy and demanding that Obama produce a copy of his birth certificate.

In private, he described Obama as “a Manchurian candidate” who obtained his Ivy League degrees only through affirmative action, according to the biography of his former “fixer”-turned-critic, Michael Cohen.

According to Cohen’s book Disloyal: A Memoir, Trump’s disdain for Obama reached such a fever pitch that he allegedly hired a “Faux-Bama” to participate in a video in which he “ritualistically belittled the first Black president and then fired him.”

Trump’s persistent “birther” conspiracy claims were firmly debunked after doctors in Honolulu, Hawaii, released a copy of Obama’s birth certificate. However, the then-president could not resist a final – and potentially unwise – retort.

The beef between Obama and Trump came to a head during the annual White House Correspondent’s Dinner, in 2011

“Donald Trump is here tonight. I know he’s taken some flack lately, but no one is happier to put this birth certificate matter to rest than The Donald,” Obama said, addressing the White House Correspondents dinner in April 2011. “And that’s because he can finally get back to the issues that matter, like, did we fake the moon landing?... And where are Biggie and Tupac?”

In footage from the evening, Trump stares straight ahead, a cursory smile across his face, as America’s first Black president roasts him continuously for over two and a half minutes.

“Say what you will about Mr Trump, he would certainly bring some change to the White House,” Obama continued, before cutting to an image of the building, reimagined as a hotel, casino and golf course, with two semi-naked women sitting in a hot tub out front. He also mocked Trump’s “credentials and breadth of experience” from working on his reality TV show The Apprentice, prompting further guffaws from attendees.

Trump launched his presidential campaign in June 2016, five years after being publicly mocked by Obama (Getty Images)

It was in that room, on that evening, surrounded by dozens of high-profile people laughing at him, that Trump decided he would run for president, those close to him have said.

After gliding down a golden escalator on June 16 2015, Trump announced his campaign for president, and over the next 16 months he branded Obama “the most ignorant president in our history,” a “disaster,” and even accused him of being the founder of ISIS.

Asked by conservative radio host Hugh Hewitt whether he meant that Obama had created a vacuum that allowed the terrorist group to thrive, Trump clarified. “No, I meant he’s the founder of ISIS. I do,” he said.

But following Trump’s victory over Hillary Clinton, his relationship with Obama flip-flopped between a one-sided bromance and outright hostility.

After Trump’s victory in 2016, his relationship with Obama flip-flopped between a one-sided bromance and outright hostility (EPA)

“We get along, I don’t know if he’ll admit this, but he likes me. I like him,” Trump told Fox News’sBill O’Reilly in February 2017. Two months later he accused Obama, without evidence, of personally wire-tapping his phones.

In the final weeks of the 2024 presidential race, Kamala Harris’ campaign has deployed Obama to stump for her in impassioned rallies around the US as well as a major speech at the Democratic National Convention in August.

During one viral moment, Obama appeared to make a jab at Trump’s manhood – referencing the “size” of his rally crowds – but making a tongue-in-cheek hand gesture, and giving a knowing look.

His appearances appear to have ripped the band-aids off Trump’s battered ego. Trump has launched fresh attacks on his former opponent, claiming earlier this month that Obama was “exhausted” and “looking older.”

Obama’s recent appearances at rallies for Kamala Harris have seemingly reignited the beef between him and Trump (AP)

The Republican presidential candidate also repeatedly called Obama “a jerk,” suggesting that he has still not forgotten the slights that occurred over a decade ago.

Roger Stone, Trump’s former political advisor, previously said that the public roasting in April 2011 was “the night that he resolves to run for president.”

“I think he is kind of motivated by it... ‘Maybe I’ll show them all,’” Stone said, speaking to Frontline PBS.

“Every critic, every detractor will have to bow down to President Trump,” added Omarosa Manigault, star of The Apprentice, and a former member of the Trump administration. “It is the ultimate revenge to become the most powerful man in the universe.”

In just a few days time, Trump’s ego will either be bolstered or deeply humiliated again.