Summary: Donald Trump's journey from a real estate mogul to the U.S. presidency was marked by several political flirtations before his successful 2016 campaign. Despite previous unsuccessful bids and public humiliations, notably from President Obama at the 2011 White House Correspondents’ Dinner, Trump used these experiences to bolster his determination. Obama's attempts to undermine Trump, including using intelligence agencies in 2016, only fueled Trump's resolve.

-Ultimately, Obama's actions in 2011 set the stage for Trump's eventual victory in 2016.

Obama’s Impact on Trump’s Presidential Ambition

Donald J. Trump has been part of the national media landscape – a Pop Cultural icon – for decades. Beginning his career as a hard-charging real estate developer in the cutthroat world of high-end Manhattan real estate, Trump built a brand for himself that was universally associated with luxury. 

Trump's Flirtation with Politics 

He then segued that brand into a national media profile that inevitably led him to the seat of absolute power: the White House. 

Since the 1980s, Trump flirted with political power. 

He famously tested the waters in the key swing state of New Hampshire at the encouragement of gonzo Republican Party strategists, like Roger Stone. Trump was never really serious. 

It wasn’t his time. 

He was too busy making money and enjoying fame to debase himself in the nasty world of American politics—especially when there were so many other qualified candidates in the mix. 

Trump continued his transition from real estate magnate to the king of tabloid stories and reality television. 

Again, Trump flirted with politics, when he ran the laughably awful campaign to become the Reform Party’s presidential nominee in the chaotic 2000 Presidential Election. 

That, too, ended in disaster. 

But it did not dissuade Trump from aspiring toward higher office. Instead, it proved to him that he needed to pick one of the two major political parties to take over.

The 2000s were a turbulent time for the political scene in the United States. The September 11 Attacks and the subsequent unpopular Iraq War of 2003 destabilized the post-Cold War political order. 

By 2008, the Great Recession ensured there was no going back to the way things were. 

Barack Obama and the New Era of American Politics

A new era in American politics was at hand—Barack Obama and his Democratic Party seized that moment. Trump, a man who had spent most of his life supporting the Democrats, was initially supportive of Barack Obama’s political ambitions.

At some point during the Obama Administration, though, this support evaporated. 

Trump became a fierce critic of the forty-fourth president—even going as far as to become the cheerleader of the ridiculous and stupid Birther conspiracy theory. A theory, by the way, that was not crafted by Donald Trump and the Republican Party. 

Instead, the belief that Barack Obama was not born in America (and therefore unqualified to be president), sprang from the deranged mind of senior Hillary Clinton adviser, Sidney Blumenthal, during the height of the 2008 Democratic Party Primary when Hillary Clinton was fighting Barack Obama for the Democratic Party’s presidential nominee that year. 

As an aside, the Democrats created a similar absurd claim (that they quickly dropped) challenging the validity of the GOP’s nominee that year, Sen. John McCain, for having been born in the Panama Canal Zone. 

The insanity was going around everywhere in 2008, about both Obama and McCain.

Trump used the notoriety he was gaining from becoming the chief cheerleader of the Birther movement as leverage to gain inroads with the Republican Party. 

Rumors began swirling in 2011 that the real estate mogul was contemplating running again for president as a Republican, to challenge President Barack Obama in the 2012 Presidential Election. 

Although most Democrats don’t want to admit it, Trump’s Birtherism was making him popular among the Republican Party base. 

Trump was a very real threat to Obama’s reelection.

Nothing Beats a Celebrity Politician Like a Celebrity

Consider this: Barack Obama was the closest thing to a celebrity the country had come to having as a president. Not since Ronald Reagan had a president understood the power of narrative and star power itself. 

But Obama was, first and foremost, a political celebrity. 

Donald Trump was a real celebrity. 

Back in 2011-12 Trump, despite his controversial and stupid Birther take, was at the top of his game.

Trump even flew to Iowa in the run-up to the 2012 election. 

I was getting involved with the GOP side of the 2012 Presidential Election at that time. Many contacts in Iowa’s Republican Party believed that Trump was serious about running that year as a Republican. 

And he’d have probably won that race, too. 

Because Trump had tapped into the Tea Party element that had become so powerful since the 2010 Midterms—an element that was enraged at the GOP establishment, which Trump would have run against that election year. Ultimately, when Trump did not run in 2012, former Republican Speaker of the House Newt Gingrich became an avatar for proto-Trumpism – and almost won in 2012.

The reality television star resonated deeply with a large segment of the population. His celebrity also gave him a degree of cachet that no other Republican running in 2012 would have enjoyed. 

Plus, Trump was a heterodox thinker; he was not a rigidly ideological conservative (or, “severely conservative” as Mitt Romney once awkwardly described himself). 

Make no mistake, Trump was the greatest threat to Obama’s reelection in 2012. 

And the Birtherism, as Trump’s courting of conspiracy theories in 2016 and beyond showed, would not have likely harmed his chances at winning in 2012 had Trump decided to run against Obama. 

Things got nastier between the forty-fourth president and the future forty-fifth president. The Obama Administration got Hawaii to release Obama’s long-form birth certificate, showing that Mr. Obama was, in fact, born in the United States (though that still did not satisfy the internet crowd or Trump for that matter). 

But it did hurt Trump’s narrative against Obama’s legitimacy as president. 

How Barack Obama Created Donald Trump 

April 30, 2011, is a fateful date indeed. 

On that evening, in Washington, D.C., Donald Trump is seated in the center of the White House Correspondents’ Dinner at which President Obama was the keynote speaker (as per the tradition of the dinner, where the sitting President delivers the keynote address and jokes with the press). 

Trump was in Obama’s line of sight from the podium the entire time during the speech. With the release of the long-form birth certificate, Obama decided to gloat; to run salt in the egotistical wounds of Donald Trump in front of all the other political, media, and business elites who purport to run America. 

In his remarks, Obama joked that “The Donald” was the happiest of all to see the resolution of the Birther conspiracy theory in order to “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?!” 

The audience laughed uncomfortably, everyone looking to see the reaction of the humiliated celebrity, who sat with a fake grin plastered across his face, betraying what many insiders say was a baleful rage.

But the forty-fourth president wasn’t done. 

He had stuck in his spikes while Trump was on the ground and was now going to twist, thereby ensuring that Trump would never again think of challenging Obama in 2012. 

Obama mocked Trump’s lack of political experience and educational credentials by bringing up the events of a recent episode of Celebrity Apprentice, in which, “the men’s cooking team did not impress the judges from Omaha Steaks. And there was a lot of blame to go around. But you Mr. Trump, recognized that there was a lack of leadership. So, ultimately you didn’t blame Lil Jon or Meatloaf. You fired Gary Busey. And these are the kind of decisions that would keep me up at night.” 

The emcee that night, comedian Seth Meyers, then trundled onto stage and quipped that “Donald Trump says he’ll run for president as a Republican but I thought he was just running as a joke.”

Trump’s face was flushed a crimson color. Humiliated and dejected, Trump, the consummate outsider (despite his ostentatious wealth and celebrity status), apparently vowed to exact revenge on Obama. 

Obama's intention was to humiliate Trump so badly that evening that he'd skulk out of the dinner and essentially stay in his lane. But Obama did not realize the ego and shamelessness of a man like Donald Trump. 

Therefore, Obama's great humiliation of Trump that evening likely had an unintended effect. Rather than dissuade Trump from running, it likely solidified his desire to run—and win.

The Bin Laden Raid Saves Obama from Trump 2012

But just two days after that disastrous outing, President Obama presided over the successful Bin Laden Raid which resulted in the death of the notorious terrorist and a major PR victory for the forty-fourth president, who truly would have been threatened by a Trump candidacy in 2012, had he not ordered that fateful raid in Abbottabad, Pakistan.