The most awkward moments from Jeb Bush’s failed presidential campaign

Dylan Stableford
Senior Writer

Jeb Bush bowed out of the race for the 2016 Republican presidential nomination on Saturday night, putting to an end one of America’s most prominent political dynasties and, frankly, one of the saddest campaigns in recent memory. Below, a look back at seven of the most awkward moments from Jeb’s bid for the White House.


Perhaps we should’ve seen it coming. In what appeared to be an ill-fated attempt to distance himself from the baggage that comes with the family name, the former Florida governor’s official campaign logo effectively replaced “Bush” with an exclamation point. It was quickly, and widely, mocked.

The Trump low-five

Debates weren’t really Jeb’s thing. During the GOP debate at the Ronald Reagan Presidential Library in Simi Valley, Calif., in September, Bush was asked what his Secret Service code name would be as president. “Eveready,” Bush replied. “It’s very high energy, Donald.” It was a good line that elicited some laughs, even from Donald Trump.

Had Bush left it there, things would’ve been fine. Instead, when Trump extended his hand in what appeared to be the low-five position, Bush went in for an all-too-aggressive slap.

Jeb Kush

At the same debate, Bush admitted to having smoked pot. “Forty years ago, I smoked marijuana, and I admit it,” he said. “I’m sure that other people might have done it and may not want to say it in front of 25 million people. My mom’s not happy that I just did.”

The awkward admission drew more laughter from the audience, led to an apology tweet and sparked the “Jeb Kush” meme online.


During a question-and-answer session at a campaign event in October, Bush was asked who his favorite superhero is.

“I don’t know,“ Bush replied. “I’m kind of old-school. I like the old-school guys, like Batman. A little dark these days.”

Again, things would’ve been fine, but for some reason Bush kept talking.

“I saw that there’s a new ‘Supergirl’ on TV,“ he said. "I saw that while I was working out this morning, there was an ad. She looked kinda … she looked pretty hot. I don’t know which channel it’s on, but I’m looking forward to that.”

When asked for a response, Melissa Benoist, the actress and recipient of Bush’s unsolicited compliment, couldn’t contain her laughter.

“I heard about it, but I don’t know what I think about it,” Benoist said on "CBS This Morning.” “I’m glad he’s excited to watch the show.”

Baby Hitler

A month later, Bush established himself as the leading pro-time-travel-in-order-to-kill-an-evil-dictator candidate in the 2016 presidential race, saying he would gladly travel back in time in order to kill baby Adolf Hitler, given the opportunity.

“Hell yeah I would!” Bush told the Huffington Post. “You gotta step up, man.”

The chest bump

Last week, former President George W. Bush hit the campaign trail in a last-second bid to boost his little brother’s chances in South Carolina, appearing in a campaign ad that touted Jeb’s record as Florida governor — and his chest-bumping ability.

‘Please clap’

No moment summed up Jeb Bush’s 2016 presidential campaign better than this one.

At a town hall event in New Hampshire earlier this month, the former Florida governor and Republican presidential hopeful asked attendees to “please clap” after his call for the next commander in chief “to be a lot quieter” was met with silence.

“I won’t trash-talk,” Bush said at the event in Hanover, N.H., a day after finishing a distant sixth in the Iowa caucuses. “I will not be a divider in chief or an agitator in chief. I won’t be out there blowharding, talking a big game without backing it up. I think the next president needs to be a lot quieter, but send a signal that we’re prepared to act in the national security interests of this country — to get back in the business of creating a more peaceful world.”

After failing to elicit applause, an exasperated Bush pleaded with the crowd.

“Please clap,” he said.