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After Obama’s remarks, comedian Seth Meyers didn’t let Trump off the hook. Many journalists noted Trump did not seem amused throughout the performance, particularly at Obama’s and Meyers’ insults. Roxanne Roberts, who sat next to Trump at the dinner, wrote in The Washington Post that Trump “didn’t crack a smile” at Meyers’ jabs. Meyers joked, “Donald Trump has been saying he will run for president as a Republican—which is surprising, since I just assumed he was running as a joke.” He continued poking fun at Trump, as Roberts noted, “lobbing jokes like grenades.”5 Roberts wrote, “In retrospect, Trump broke the classic rule of political humor that says that the only response to a joke about you is to laugh harder than anyone else in the room. Whatever he was thinking, Trump looked unhappy and gave pundits a reason to pounce.”6 Trump only fueled the fire when he didn’t attend any after parties, and instead headed directly to his jet from the dinner.

The following day, Trump told Fox News that he “really understood what I was getting into” saying, “I didn’t know that I’d be virtually the sole focus. I guess when you’re leading in the polls that sort of thing tends to happen. But I was certainly in a certain way having a good time listening.”7

If he was listening, what he heard did not appear to please him the slightest. He attacked Meyers directly. “Seth Meyers has no talent,” Trump said in an interview with Michael Barbaro of The New York Times the day after the dinner. “He fell totally flat. In fact, I thought Seth’s delivery was so bad that he hurt himself.”8 He told Barbaro the evening was “like a roast of Donald Trump.” Still, Barbaro described him as “clearly reveling in the attention, if not the content.”9

In retrospect, the events of the 2011 White House Correspondents’ Dinner may have at least partially motivated Trump to run in 2016. The New York Times’ Maggie Haberman and Alexander Burns wrote, “That evening of public abasement, rather than sending Mr. Trump away, accelerated his ferocious efforts to gain stature within the political world. And it captured the degree to which Mr. Trump’s campaign is driven by a deep yearning sometimes obscured by his bluster and bragging: a desire to be taken seriously.”10

Clearly stung by the dinner jokes, it would be natural to see how Trump might relish revenge. Harnessing the power of the conservative poll numbers running for President in 2016 would give him the power of dismantling Obama’s legacy himself.

Trump Enters Politics

When Donald Trump announced his presidential run on June 16, 2015, he entered an unusually large field of eleven major Republican candidates seeking the White House. By the end of July, that field would expand to an unprecedented seventeen major Republican candidates, a hodgepodge that included nine current or former governors, senators, a retired neurosurgeon, and the former CEO of Hewlett Packard.11, 12

Polls early on in the contest showed Trump with an immediate edge over most of the candidates, with a June 26–28, 2015 CNN/ORC national poll showing him polling at 12 percent among Republicans, second after former Florida governor Jeb Bush at 19 percent.13 By July 22–25, 2015, a CNN/ORC poll showed the New York businessman topping the polls at 19 percent, with Bush trailing at 15 percent.14 Always outlandish, his brash style and ability to “tell it like it is” attracted crowds of admirers. He was an instant success among the conservative fringe and had the ability to bring that fringe into the mainstream.

The hallmark of his campaign was using hyperbole and personal insults with just a touch of Orwellian double speak. For example, he would make contradictory statements, on one hand praising veterans but insulting John McCain for being shot down and spending years as a prisoner of war in Vietnam. On July 18, 2015 Trump threw out an offhand remark about McCain. “He’s not a war hero,” Trump said. “He was a war hero because he was captured. I like people who weren’t captured.”15 When pressured he would claim he never said any such thing and allow the next outrageous statement to wash over the last one.

Despite his high poll numbers, most of the media and electorate did not initially take his campaign seriously. The Huffington Post went as far as to announce in July 2015 it would run all Trump-related stories in the Entertainment section. “Our reason is simple: Trump’s campaign is a sideshow,” the announcement read. “We won’t take the bait. If you are interested in what The Donald has to say, you’ll find it next to our stories on the Kardashians and The Bachelorette.”16

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