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The 17 saddest moments of Jeb Bush’s very sad campaign

Fox News

Jeb Bush launched his presidential campaign's exploratory committee on December 16, 2014, the presumptive Republican nominee. He ended his campaign on February 20, 2016, a broken man.

Bush's campaign (and the pro-Jeb super PAC Right to Rise) spent more than $100 million on his run. He won no states. And for the past several months, he's been in the news mostly for all the wrong reasons: desperate donors, misspent money, jokes that aren't really jokes. He's been a loser for almost as long as he was a presumptive winner.

The slow, torturous twilight of Jeb's campaign offers a couple of lessons. For one thing, it throws the political skills of his brother George W. Bush into sharp relief: W might have gotten flak for being "dumb," but seeing what happens to someone with all the same advantages makes it clear how much of W's success was his own. For another thing, it's a reminder that (for all the problems associated with money in politics) it's extremely hard to buy a presidential campaign.

But if Jeb's campaign was born with a silver spoon in its mouth, it ended screaming in its high chair with strained peaches all over the floor. Yes, Jeb was bullied relentlessly by Donald Trump. But the consistent ineptitude of Jeb's own allies, and his own dogged, hopeful, pathetic awkwardness, was truly what did him in in his campaign. When he finally, mercifully dropped out Saturday night, you could almost hear the collective sigh: Poor Jeb.

Let us remember.

1) The moment when Jeb's family "gathered to rescue" him (October 26)

Even in late October, it was clear that Jeb wasn't just underperforming or waiting for his surge. He was legitimately in trouble.

The Politico headline: "Bush family gathers to rescue Jeb."

The key quote:

"The patient is either in intensive care and in need of some good doctors who can save him or being put into hospice and we’re going to see a slow death," said one K Street lobbyist supporting Bush.

2) The moment when Jeb Bush had nothing to do but email with some random dude about football (November 4)

Curry Shoff, a recent grad of the University of Texas — in an email exchange posted the next day by Deadspin — shot off an email to Jeb Bush asking him what he thought of the school's new coach.

Jeb responded. Within 45 seconds.

When Shoff replied in disbelief, Jeb responded, "Sadly it is me and after a 16 hour day I'm going to sleep."

Sadly indeed, Jeb. Sadly indeed.

3) The moment when the most-Googled question about Jeb was "Is Jeb Bush still running for president?" (November 10)

4) The moment when the internet realized redirected to Donald Trump's campaign site (December 7)

Jeb Bush's campaign never bothered to buy So the person who owned it, in fall 2015, decided to do something else with it instead: redirect it to Donald Trump's website.

saddest Jeb Bush internet screengrab (Dara Lind)

At the time, it just seemed like a characteristic Jeb bumble: How, after immigration reform activists snapped up and became a testament to the layoffs Fiorina ordered at Hewlett-Packard, could Bush's people not lock up But like so many of the early entries on this list, which seemed honestly funny back before Jeb started looking so openly pathetic, it now packs a surprising amount of pathos.

5) The moment when Jeb's campaign accidentally hyped the "final debate" (December 15)

What Jeb's campaign meant: the final debate of 2015. What Jeb's campaign said:

6) The moment when Jeb's Super PAC put up an anti-Trump Iowa billboard that was so bad that it was effectively a pro-Trump billboard (January 7)

Jeb Bush got in a decent dig at Trump at that "final debate," calling him "unhinged." Jeb's Super PAC liked that. They liked it so much that they bought a billboard saying it. In Iowa.

My colleague Andrew Prokop, who called the billboard "cartoonishly bad," laid out the problem here:

The problem here is that it's a bit unclear whether this is supposed to be an anti-Trump billboard ... or a pro-Trump billboard.

After all, Bush is not at all popular in Iowa!

When the candidates' favorability ratings among likely Republican caucus-goers are measured, Trump is a good deal more popular than Bush (whose net favorability is underwater, meaning that more people view him unfavorably than favorably).

So when Republicans read a simple quote from the unpopular Jeb Bush condemning Trump, it might well make them like Trump more.

7) The moment when Jimmy Kimmel had DJ Khaled offer Bush a personalized pick-me-up (January 14)

DJ Khaled is a Snapchat legend. He is 2016's best motivational speaker. And in mid-January, he was the only man who could have cheered up Jeb Bush.

Kaitlyn Tiffany at The Verge pointed out why Khaled's advice was so sage:

The advice that Khaled offered Jeb is reasonable advice, though notably unrelated to winning the presidential election. That's because Khaled, while an optimist, is also a pragmatist and a true friend. He could tell just by looking at Jeb! that there were some physical and emotional health issues to tackle first.

Jeb, to his credit, made an effort.

8) The moment when donors were told, "I need you to throw away money on Jeb — out of loyalty" (January 15)

The Politico headline: "Bush donors await green light to jump ship."

The key passage:

POLITICO talked to nearly two dozen major donors, and most say they are waiting for what one veteran Republican and former Bush 43 administration appointee described as the "family hall pass" to jump to another campaign after the New Hampshire primary.

"I’m resigned to it being over, frankly. It’s really disappointing," said one top Bush Wall Street donor. "I’d urge him to get out after New Hampshire if he doesn’t do well, but he probably won’t."

9) The moment when Jeb Bush got so fed up with his Super PAC that he started complaining about Citizens United (January 23)

Jeb Bush's Super PAC, Right to Rise, spent an unbelievable amount of money to get Jeb elected. But even a week before the Iowa caucuses, it was beginning to become clear that it wasn't going to do much good.

So when Jeb responded to a question about Citizens United by saying it "creates a mess. Believe me, I'm living through it right now," it was a surprising moment of heterodoxy from the campaign's most establishment Republican. But it was also a flash of frustration from a candidate who had to watch millions upon millions of dollars being, well, thrown away in the name of support.

10) The moment of "Mission accomplished!" (January 28)

It starts out as a standard interaction between a reporter and a (minor) candidate a few days before an election: Reporter (in this case, CBS's Major Garrett) asks whether candidate (Jeb) will pleasantly surprise observers when the votes are counted. Then it becomes something very, very sad.

Was Jeb deliberately referencing one of the most notorious moments of his brother's presidency? Who knows. But that wouldn't exactly make it any less pitiful.

11) The moment when Jeb's last rally before the Iowa caucuses was interrupted by people demanding to be paid for filling the seats (February 1)

This is not the note you want to strike with your last rally before Iowans go to the caucuses:

Moments after Bush began speaking two young men stood up and very conspicuously demanded to be paid for their "seat filling."

"We’ve been here for over two hours and we haven’t gotten paid for our time," one man said, unleashing a torrent of boos and jeers from the audience.

"That is such — get out of here, man," Bush shot back.

Admittedly, this could have been a dirty trick by another campaign (some speculated it was Marco Rubio's). But even if it did, it only worked because it was moderately plausible that Jeb would need to pay people to show up to his events.

12) The moment when Jeb Bush spent $2,800 per vote in Iowa (February 1)

Jeb did not in fact surpass his accomplished-ly low expectations. If anything, he underperformed.

And in doing so, he spent $2,800 per vote.

13) The moment when his Super PAC was still running ads in Iowa after the caucuses (February 2)

It's things like this that made Jeb Bush rue the day the Supreme Court issued Citizens United:

14) The moment of "Please clap" (February 3)

Another moment when Jeb Bush was probably joking, but joking to cover the pain.

15) The moment when Jeb was so excited to hear that he might have won a guy's vote that he ran over to hug him (February 4)

The video's title says it all: "Jeb hug — sad times."

16) The moment when a town hall turned into a group brainstorming session about saving Jeb's campaign (February 16)

Jeb didn't hug enough New Hampshirites, apparently. By the South Carolina leg of the campaign, it was pretty clear he was done. By the last week of his campaign, Jeb was such a pitiful figure that at a town hall event, instead of asking questions, voters started giving him tips:

17) The moment when Jeb finally, tearfully dropped out (February 20)

Goodbye, poor Jeb Bush. Hopefully you'll spend the next several months on a beach, playing checkers with your wife and not paying any attention to the election. We'll miss you.