Jeb’s Most Awkward, Dignity-Losing, Cringey Moments: The Definitive Guide

Start your day with TPM.
Sign up for the Morning Memo newsletter

Jeb Bush isn’t running the campaign he thought he’d be running.

Long considered the heir apparent in the 2016 Republican race, Bush is now campaigning like a man with nothing left to lose. He’s been polling in the mid-to-lower tier of the still-crowded GOP field for months. He finished a disappointing sixth in the Iowa caucuses, more than 20 points behind Sen. Ted Cruz (R-TX) and Donald Trump, and shelled out nearly $3,000 for each vote he earned there.

But Bush’s fall from grace hasn’t been boring. The candidate who once pledged to “joyfully” campaign now regularly cracks self-aware jokes about his less-than-stellar standing in the race. These moments from the campaign trail are captivating, mostly because it’s difficult to discern whether they capture genuine humiliation or showcase Bush’s famously dry wit.

Either way, these moments get people talking about Bush again, which is good news for the ex-Florida governor’s campaign. Here’s a look at some of his best self-deprecating moments.

“Macbook Pro, baby”

Bush loves his Apple products. But his awkward attempt at folksiness in a campaign video called “Jeb’s Silicon Valley Favorites List” made the video far more memorable.

In the video, Bush picks his favorite devices in an either/or of tech toys, like iPhone or Blackberry. When picking between a laptop or an iPad, Jeb says: “Macbook Pro, baby.”

The cadence is off, and he offers a bashful, pursed-lip smile, which was enough to spin the line into an online meme at warp speed. You really just have to watch it for yourself:

Jeb doesn’t understand how to wear a hoodie

As part of a wild and crazy bid to introduce himself to voters, the campaign launched #JebNoFilter, a series of videos of the candidate doing apparently quirky things.

One unintended byproduct: proving once and for all that Bush has never worn a hoodie (in the “Silicon Valley Favorites” video, he’d said he preferred his collared shirt over both a Steve Jobs-style turtleneck and a sweatshirt).

“I’m wearin’ my hoodie,” he says in one clip. “Eat your heart out, Zuckerberg!”

Jeb’s gets his own “mission accomplished” moment

In an interview during the run up to the Iowa caucuses, CBS News’ Major Garrett asked the Republican if he could still be a “surprise story” on caucus night.

“Yes, because the expectations are so low,” Bush deadpanned with a smile.

Garrett diplomatically responded, “Well, you have succeeded there, governor.”

“Mission accomplished!” Bush said, pumping his arms in the air.

Jeb begs crowd: “please clap”

In a moment that was read as both a joke and a desperate plea, Bush asked the crowd at a New Hampshire campaign event to reward his enthusiasm on the stump.

“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 interest of this country, to get back in the business of creating a more peaceful world,” he said, leaving a beat for the applause to begin.

When it didn’t, his voice dropped an octave as he said, “Please clap.”

Jeb gives swing voter a big bear hug

Video circulated online Thursday showing Bush interacting with a self-identified swing voter. In the snippet, a male voter tells Bush from offscreen: “You might swing my vote!”

You can see Bush’s eyes light up as he strides over to the voter and gathers him into a rapturous hug:

Latest News
Masthead Masthead
Founder & Editor-in-Chief:
Executive Editor:
Managing Editor:
Associate Editor:
Editor at Large:
General Counsel:
Head of Product:
Director of Technology:
Associate Publisher:
Front End Developer:
Senior Designer: