The 25 Biggest Gaffes of the 2016 Presidential Race

DEAD BROKE

The 2016 cycle was in its prenatal stages when Hillary Clinton made her first major gaffe.

"We came out of the White House not only dead broke, but in debt," she told Diane Sawyer in a June 9, 2014 interview, back when her presidential bid was only a steadily approaching inevitability.

Almost every pol has some story of humble beginnings or financial affliction that usually falls somewhere on the spectrum between inspiring and insulting. Clinton's comment missed that spectrum entirely and landed off in the ultraviolet ranges of absurd and outright laughable. True, the Clintons had heavy legal bills and multiple mortgages when Bill exited the presidency in 2001. But they also had almost $2 million in the bank, and had made down payments on multi-million dollar homes in Washington, D.C. and in Westchester. Not to mention the former first lady had just picked up a U.S. Senate seat, with its then-salary of $145,100 a year, and massive amounts of cash in speaking fees both quickly began raking in—which would haunt Hillary Clinton all the way down the campaign trail. The claim also resuscitated memories that the Clintons had absconded from Washington not only with a nice-sized sack of cash, but also with several pieces of White House furniture.

IRAQ WAR FLIP-FLOP

Ah, it seems such a long time ago now, before Donald Trump entered the presidential race and ex-Florida Gov. Jeb Bush was the GOP frontrunner. Pundits were even predicting 2016 would be a reprise of 1992, which pitted a Clinton against a Bush and an erratic, incoherent billionaire nobody seriously expected to actually get into the race, much less have any shot at winning. How wrong they were.

The American public first witnessed Bush's uncanny awkwardness and unbelievable ability to bobble a soundbyte on May 10, 2015, when Fox News released a clip from an interview the candidate gave host Megyn Kelly (now of "wherever" fame).

Asked if he would have authorized his brother's 2003 invasion of Iraq, Bush answered he "would have...so would almost everybody that was confronted with the intelligence they got."

Which was a terrible answer, but not as terrible as what came next. When he realized this wasn't a popular position to hold, Jeb(!) insisted he had "misheard" the question and decided to backtrack in a conversation with Fox Host Sean Hannity. Badly.

“I don’t know what that decision would have been.”

Bush took another swing and miss a couple days later, declaring that he "would not have engaged." By then, though, it was clear Bush had failed to learn the single most important political lesson from his brother's presidency: Gaffes go over much better if you deliver them in a twangy Texas accent.

DON'T GET CAPTURED

The first rule in American politics is this: everybody loves veterans. That's not to say anybody does much to actually help them once they get elected—presidents from both parties have shamefully neglected former servicemembers for decades. But so long as you're on the campaign trail, you shake their hands and wave the flag and announce how much you appreciate them at every available opportunity.

At least, that was the tradition up til July 18, 2015, when Donald Trump scoffed at the service record of Arizona Sen. John McCain, who spent five years as a captive of the North Vietnamese (two of them in solitary confinement) after they shot down his fighter plane in 1967. McCain suffered repeated beatings and torture, so severe that to this day he can't lift his arms above his head.

But apparently that wasn't good enough for Trump, who received four draft deferments during Vietnam, because he told the Family Leadership Summit in Iowa the senator “was a war hero because he was captured. I like people who weren’t captured.”

This was such a faux pas that the New York Post bid the chickenhawk mogul "Don Voyage" on its front page the following day, predicting the end of his contention for the nomination. But, like everybody else at that point, they still thought they were in something resembling a normal election year.

ANCHOR BABIES

Of all the awkward, flailing attempts of the 17 other GOP candidates to be more Trump-y, but not too Trump-y, Jeb Bush's decision to drop the term "anchor babies" into an August 24, 2015 speech on immigration—and to defend it afterward as "frankly more related to Asian people"—narrowly beats out Wisconsin Gov. Scott Walker's call to build a wall on the Canadian border.

It completely messed up Bush's image as an immigrant-loving, nice guy version of Mitt Romney (i.e. what the GOP's autopsy report had ordered after 2012).

The wonkish ex-governor was clearly uncomfortable deploying an abusive broadside in an important policy discussion, and it showed when he sought to give it some nuance while talking to the press.

Maternity tourism for Chinese elites is real, after all, but none of that came across when Bush threw out the phrase "Asian people" as if that would somehow sound better than blaming Hispanics. Lesson from the Donald: If you don't have something nice to say, say it as loudly and unapologetically as possible. If some people get angry, just repeat it. And if a lot of people get angry, deny ever saying it at all.

RACIALLY CHARGED RETWEETS

There's dog whistle politics, and then there's promoting nonsensical statistics fabricated by neo-Nazis alongside a threatening image of a black man holding a gun. It's never been clear if Donald Trump doesn't know the difference, doesn't care or is simply the world's most thoughtless, careless, ill-informed Twitter user. Or maybe with this November 22, 2015 retweet, and in the countless incidents before and since, he really is winking at the racist "alt-Right."

It just doesn't seem like a community consisting mainly of a few thousand people afraid to show their faces on social media is that big a voting bloc. But then again, look where we are now.

GOING NUCLEAR

If you were to ask a person on the street what the president's single most important responsibility is, some would say the annual pardoning of the White House's Thanksgiving turkey. Those people would be weirdos. Most would probably tell you it's custody of the U.S.'s 6,430 active nuclear warheads.

After all, a president's decision to use his Gold Codes and authorize a nuclear strike could quite literally trigger human extinction. In such an event, the commander-in-chief could launch a strike from bomber planes, from submarines and/or from inter-continental ballistic missile silos on American soil—a three-pronged strategy known as the "nuclear triad." And by "commonly" we mean "not by Donald Trump," since the brash businessman showed he had no idea what the U.S.'s nuclear delivery capabilities are at the fifth Republican debate on December 15, 2015.

In answer to a question from moderator Hugh Hewitt about the system, Trump coughed up this hairball: “I think to me, nuclear, is just the power, the devastation is very important to me."

Florida Sen. Marco Rubio was nice enough to intervene and and explain the subject a moment later.

CHINA IN SYRIA

In an alternate universe, instead of getting sandbagged by his own policy flubs and out-and-out personal weirdness, Dr. Ben Carson capitalized on his evangelical support in Iowa and general outsider appeal to become his party's 2016 presidential nominee. Presumably in that same universe China invaded Syria, because we pretty much can trace the downward trajectory of the retired neurosurgeon's campaign to the claim at the November 10, 2015 debate that such an astounding ground campaign was underway.

"The Chinese are there," Carson informed the audience in Milwaukee. It seemed the good doctor but bad candidate was in possession of intelligence alien to every national security expert and agency, as well as to the White House itself.

And who knows—maybe somewhere out there, on some parallel planet, some other China is planting its red flag in their world's Aleppo.

APPLAUSE

"Please clap."

His actual withdrawal from the race didn't come until two primaries and almost three weeks after Jeb(?) said those two sad, sad words, but in a way they made for a sad, sad coda to his sad, sad campaign. A famous name, a presidential bloodline, enormous goodwill from party leadership and more than $103 million in super PAC cash couldn't win him more than 11 percent in a single Republican primary.

Even sadder, Bush had been implicitly contrasting himself with Donald Trump seconds before his plea for applause.

"I won't trash talk. I won't 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," he had told the crowd at the Hanover Inn in New Hampshire.

RUBIO ON REPEAT

As Jeb(...) faded, the GOP leadership began to gaze longingly at the suave, youthful figure of Marco Rubio. He had less name recognition than a Bush, of course, but overall he was an upgrade on his state's former governor: fresh-faced, reliably conservative on economic issues, malleable on matters like immigration—and not only was he married to a Hispanic woman, he was a Hispanic man himself. After a decent third-place finish in Iowa, it seemed yet another first-term senator could march on D.C.

Then came the February 6 debate in New Hampshire, just days before the Granite State primary.In a confrontation with New Jersey Gov. Chris Christie, the golden boy melted like wax in the spotlight. When Christie accused him of relying on a "memorized 25-second speech," Rubio repeated the same 25-second speech he'd made moments before—twice.

The crowd booed, Rubio sweated a waterfall and Trump crushed the competition in the first-in-the-nation primary.

Christie dropped out while Rubio hung on, and the senator even enjoyed a short resurgence—placing second in the South Carolina primary and humiliating Trump in the February 25 debate. But Christie rained on Rubio's moment in the sun yet again when he endorsed the Donald the very next day.

THE THIN WHITE DUKE

That creepy, vampiric-looking character up above is David Duke, and if you don't know who he is, you're probably fine with accepting his endorsement for the presidency. Or at least Donald Trump was.

"I don't know anything about David Duke. I don't know anything about what you're even talking about," Donald Trump told CNN host Jake Tapper on February 28, 2016, when asked about the ex-Ku Klux Klan leader's declared support.

The candidate added he would have to "do research" before rejecting the racist's blessing.

It was another occasion where Trump's self-described "world's greatest memory" inexplicably misfired. Trump had disavowed Duke's backing three days earlier, and had attacked the white supremacist while running in the Reform Party primary in 2000. It was a disavowal Trump would repeat on February 29, when he claimed CNN's "lousy earpiece" had translated Tapper's question about "David Duke" to one on "various groups"—even though Trump had repeated Duke's name in his answer to Tapper the day before.

IN THE GHETTO

It's written somewhere (on page 571 of The Bonfire of the Vanities, I think) that every liberal Jewish politician from New York City must inevitably choke on race. Of course, five decades in snow-white Vermont didn't help Sen. Bernie Sanders any. In courting leftist elements of the Democratic electorate, the socialist senator unintentionally invited the attention of the Black Lives Matter movement, leading to embarrassing incidents at the Netroots Nation conference in Phoenix and at a Social Security rally in Seattle.

But Sanders' squeamishness and reflexive cringing on African-American issues was never on better display than at the Democrats' March 6, 2016 debate in Flint, MI.

"When you're white, you don't know what it's like to be living in a ghetto. You don't know what it's like to be poor," he said.

Never mind that Flint itself is 35 percent non-Hispanic white, and uniformly poor enough to qualify as a ghetto. Never mind that there are nearly twice as many poor whites in America than poor blacks. Sanders was trying to make an appeal to African-American voters by parroting stereotypes about them. Blacks may have the highest rate of poverty of any ethnic group in the U.S., but between two-thirds and three-quarters of them live above that line. And Sanders had failed once again to speak to them.

THANKS, NANCY

After Nancy Reagan died on March 6, 2016, Hillary Clinton paid a bizarre and bewildering tribute to her fellow former first lady.

"Because of both President and Mrs. Reagan—in particular Mrs. Reagan—we started a national conversation when before nobody would talk about it, nobody wanted to do anything about it. And that too is something that I really appreciate with her very effective, low-key advocacy," Clinton told MSNBC.

She wasn't talking about drugs or Alzheimer's disease or stem cell research or gun control or any of the other issues Nancy Reagan had famously agitated on during her 94 years on earth. She was talking about AIDS.

A special enmity toward the Reagans hangs on in the parts of the gay and HIV-positive communities that can remember the 80s. Many saw the Reagans as deliberately slow to address the problem, even as tens of thousands of Americans became infected and died. And Nancy Reagan in particular declined to help their ailing friend Rock Hudson obtain treatment for the disease in France. Clinton's comments won her a swift rebuke from a number of her gay supporters, including the president of the Human Rights Campaign, Chad Griffin.

ABORTION PUNISHMENTS

It was at this point that Donald Trump's strategy of just winging it on policy started to hurt him. But by the time he told Chris Matthews on March 30, 2016 that he thought there "has to be some form of punishment" for women who undergo abortions, it was too late to stop him from becoming the GOP nominee. The gaffe locked in a now-familiar pattern of him having to spend days disowning his outrageous statements instead of doubling down on them. And that sucks up precious airtime that could be used to call attention to Hillary Clinton's vulnerabilities. This comment also didn't help lift his rock-bottom favorability ratings among women.

THE SWIPE HEARD ROUND THE WORLD

After a string of primary losses in the Midwest, Hillary Clinton hoped to break Bernie Sanders' momentum with a victory in their shared home state: New York. Sanders was a son of Brooklyn, but Clinton had lived (and kept her email server) in Westchester for almost 17 years. And her eight-year stint representing New York in the U.S. Senate meant she had plenty of local political allies. She didn't have Sanders' plangent Kings Highway intonations, maybe, but surely she could prove her Big Apple bona fides in a well-choreographed media event ahead of the April 19 primary.

Or not.

On April 7, in front of dozens of watchful cameras, Clinton wielded a Metrocard at the 161st Street-Yankee Stadium station with all the proficiency and aplomb of a tourist from Park Ridge, IL. It took her five tries to finally get through.

To be fair, though, Sanders thought the turnstiles still took tokens. And New York Democrats still went with her on primary night.

BERNIE ON ISRAEL

Bernie Sanders is a member of a dwindling species in American politics: the centrist on Israel. Why that's so small a minority was clear whenever the senator got pelted with questions about his position on the Jewish State. And none of those occasions was more embarrassing than his conversation with the Daily News on April 1, 2016—where he claimed Israel's clash with Hamas in Gaza two years ago had killed "10,000 innocent people."

That figure is almost five times higher than any estimate of the total casualty count, militants and civilians combined. And it came right ahead of the New York primary, with its many Jewish Democratic voters. Worst of all, it drew more scrutiny to Sanders' stance on Middle Eastern affairs, which not only illustrated his vulnerability on international issues in general, but also forced him to scramble for a foothold on the dwindling middle ground in the most contentious land dispute on the planet. Defending the Jewish State's right to exist couldn't have pleased his base of hard-lefties—who have been anti-Israel since Nasser aligned with the Soviet Union in 1957—while calling the 2014 Israeli retaliation against the Palestinians "disproportionate" naturally displeased older Jewish voters.

WITH ENDORSERS LIKE THESE...

It was obvious all through 2015 that Mayor Bill de Blasio was desperate to make an impression on the presidential race. From his "Progressive Agenda" events at Gracie Mansion and outside the Capitol building in April and May 2015, to his scuttled plans to host both Democratic and GOP debates, the mayor seemed like an over-eager eight-year-old bouncing up and down to get the grown-ups' attention. Well, he finally got a little of that precious national notice he craved in April of this year—but it didn't come quite the way he wanted it.

The mayor brought Hillary Clinton as his surprise guest to the April 9 Inner Circle show, an annual satire of NYC politics put on by reporters. De Blasio and Clinton did a little routine of their own onstage, where Clinton tweaked de Blasio over his belated decision to jump aboard her bandwagon with the rest of the political class.

The mayor's excuse?

"I was running on CP time," he said.

That abbreviation usually stands for "colored people time," and hearkens to the stereotype that black people like to show up late. But here, Clinton helpfully explained, it meant "cautious politician time."

Ba-dum tsh.

The people in the room groaned and let it go. But a video of the skit escaped into the national news stream a couple days later, provoking some murmurings about sensitivity and the duo's horrible, horrible comic delivery.

Clinton naturally blamed the bit of curdled comedy on the lesser Dem—and de Blasio got to be the laughingstock of the whole country and not just New York for a change.

Would people have gotten so upset if it hadn't been such a godawful creaking awkward joke? The world may never know.

STAR OF DAVID OR 'PLAIN STAR'?

If you thought "CP Time" was impolitic, on July 2 Donald Trump posted a picture on Twitter of a Star of David on top of a pile of cash next to Hillary Clinton's face. You'd think after the aforementioned crime stats incident (or after engaging a user called "@WhiteGenocideTM," or blasting out a quote from Benito Mussolini, or...) Trump would have learned to wait a full 15 seconds before hitting the "Tweet" button. But not only was the gaffe itself bad, the attempts at damage control made the BP oil spill response look a virtuoso performance.

About two hours after the image went up on Trump's account, somebody took it down and replaced it with a similar picture that swapped the hexagram with a circle (bearing the same legend "Most Corrupt Candidate Ever!"!). Believe it or not, it actually got worse from there.

As reports arose that the first image had originated on a white supremacist message board, Trump insisted that the shape was a "sheriff's star," or "plain star," not a Star of David.

And he continued to sulk about the coverage online and in public for days afterward, even when the media was clearly ready to move on. This refusal to just let some bad press go would haunt him later on.

ON THE PENCE

Awkward.

That's the only way to describe Donald Trump's reported last-minute attempt to drop Indiana Gov. Mike Pence from the Republican ticket. Trump had taken weeks to choose between Pence, New Jersey Gov. Chris Christie and former House Speaker Newt Gingrich. Key advisers urged him to pick the Hoosier State pol, and the Queens-born businessman was set to announce that selection on July 15, 2016.

But the belligerent billionaire was apparently already getting buyer's remorse by the night before, since he used the tragic terrorist attack in Nice, France as an excuse to postpone the press conference. With Pence and his family sitting in a hotel in Manhattan, Trump reportedly made several frantic phone calls to see if it wasn't too late to make another pick.

No wonder Pence left him hanging for that kiss at the convention the next week.

WHOSE LINE IS IT ANYWAY?

In the four-day bad acid trip that was the GOP's convention in Cleveland, a few moments of particular surrealness still stick out. One of those was Melania Trump's speech on the first night, July 18, 2016. Her husband's decision to introduce her onstage was weird enough: not only did it sunder years of tradition, but he entered in full American Gladiators mode, appearing in silhouette to blasting strains of "We Are the Champions." Everybody should have known something was up when Melania's speech came out so bland.

Before the night was out, everybody knew what that was: she'd lifted a paragraph and a half of it from Michelle Obama's address to the 2008 Democratic convention. The Trump team put out a half-dozen contradictory statements excusing and explaining the obvious cribbing—not one of them remotely plausible. The blame eventually got unloaded onto a longtime Trump ghostwriter with the unlikely name of Meredith McIver. Apparently at some point during the composition process Melania (being a longtime admirer of the first lady) read parts of the Obama speech over the phone to McIver, who copied them down without realizing that they were quotes.

It seemed almost like the strategy was to confuse everybody to the point where they stopped caring. If you believed there was any strategy at all.

PUTIN AND TRUMP, BFFS

Donald Trump's inexplicable affection for Russian strongman Vladimir Putin was unnerving all along. The way he questioned whether the ex-KGB agent had really murdered journalists and political critics. The way he praised the Russian intervention to prop up Syrian dictator Bashar al-Assad's dying regime. The way he stared for hours at the famous photos of the shirtless autocrat bestride a black-maned stallion, icy Slavic eyes surveying the vast Siberian tundra in the pale green bloom of a Eurasian August (we imagine).

There was also his well-documented business ties to the former Soviet Union, and his decision to hire Paul Manafort as his campaign chairman/manager—Manafort, who had spent six years as a consultant to Viktor Yanukovych, the deposed Kremlin-aligned kleptocrat of Ukraine. And Trump's campaign had fought to soften language in the GOP platform about defending Ukraine from Russian aggression.

Then, on July 20, 2016, the night before he was due to speak at his party's convention, Trump told the New York Times he might not ride to the defense of American allies in Eastern Europe if Putin attacked. "Have they fulfilled their obligations to us?" Trump asked, in answer to a question about whether he would offer military support to new Baltic members of the North Atlantic Treaty Organization in the event of an invasion. Like with so many of his policy proclamations, it's hazy what Trump meant by that. Most likely he was referring to the NATO-ordained goal that all member states devote two percent of their gross domestic product to defense—a threshold only the U.S., Great Britain, Greece and, weirdly enough, Estonia are currently meeting.

In any case, it induced panic in parts of the former Soviet empire now feeling Putin's cold blue gaze on their territory.

The campaign initially denied Trump ever made the above statement, and he seemed to inch away from it in his acceptance speech the next night. But his attachment to Putin lingered, as we'll see.

E-MAILS, AGAIN

Russian hackers' release via Wikileaks of roughly 20,000 internal emails hacked from the Democratic National Committee, on the Friday before the party's convention in July, was a veritable grab-bag of gaffes from the Dem establishment. The emails revealed that the DNC, despite its professed impartiality in the primary, held Sanders and his campaign in sneering contempt and had sought to seed the media with a handful of stories damaging to him (including a particularly ugly one about his religious beliefs, or lack thereof). None of this was hugely shocking: an organization full of devout D.C. Democrats headed by the co-chair of Clinton's 2008 campaign (Florida Congresswoman Debbie Wasserman-Schultz) was never going to be truly neutral. And most of the anti-Sanders emails were from late in the race, when not only party machinery but the laws of mathematics were stacked against him.

But the news appealed to his Millennial supporters' feelings of alienation and victimhood (alienation and victimhood being the primary two Millennial emotions), and led to Wasserman-Schultz abdicating her position of DNC chair.

It also led to several disruptive incidents early in the convention, though the Sanders fans' inflamed tempers cooled considerably after the first night of speeches.

But given all the problems they've caused the party this cycle, maybe it's time for the Democrats to find another way to exchange ideas besides emails. I hear Snapchat is fun.

GOLD-STAR SCREWUP

If it's a rule of politics not to attack veterans (see: John McCain), perhaps a follow-up rule might be: don't criticize the families of soldiers who died at war. And definitely don't compare your "sacrifices" to their dead children. After the saintly-seeming parents of the late Army Captain Humayan Khan denounced Donald Trump's attacks on Muslims at the Democratic convention, Trump made the unbelievably bad decision to hit back.

In an interview with George Stephanopoulos on July 29, 2016, Trump noted Khan's father Khizr had done all the talking—and suggested his mother Ghazala "wasn't allowed" to speak. Trump also disputed Khizr Khan's claim he had "sacrificed nothing."

“I think I’ve made a lot of sacrifices,” he said. “I’ve worked very, very hard. I’ve created thousands and thousands of jobs.”

What's worse, Trump refused to end the feud and continued to hit the Khans in press statements and over Twitter for days afterward. This not only provoked opprobrium from across the political spectrum, but ensured that one of the most poignant moments from the Democratic summit would get to run on a near-continuous loop on TV.

HACK MY OPPONENT, PLEASE

Maybe Donald Trump's next book can be called "From Russia, With Love." The Republican's call for Russian hackers to track down Hillary Clinton's deleted emails was the consummation of his long-running long-distance bromance with Vladimir Putin (Paul Manafort having to resign from the campaign when evidence arose that he'd lobbied the U.S. on behalf of Viktor Yanukovych's government was sort of the uncomfortable pillow talk afterward).

“I will tell you this, Russia: If you’re listening, I hope you’re able to find the 30,000 emails that are missing,” Trump announced at a news conference in Florida.

The candidate later claimed the comment was "sarcastic," and it very well may have been, but that doesn't mean it wasn't also an incredibly irresponsible and ill-considered thing to say.

It was clear after the DNC hack that the Russians weren't just rooting for Trump but actively trying to boost his bid for the White House through strategic information dumps. Now, those leaks will look even more suspect than before.

And nobody, Republican or Democrat, wants to elect a Manchurian—or Muscovian—candidate president.

SECOND AMENDMENT PEOPLE

The risk in compiling a list like this, in a year like this, with a candidate like Donald Trump topping a major party ticket is that he could very well be making another gaffe while this piece is in editing. The deleted scenes from this blooper reel could have filled another 25 frames, and half of those would be Trump ("thousands and thousands" of Muslims celebrating on 9/11, mocking a disabled New York Times reporter, appearing to evict a baby from a rally).

But he'd be hard-pressed to top his suggestion that the solution to either a Clinton presidency or a Clinton-appointed Supreme Court majority would be assassination.

"If she gets to pick her judges, nothing you can do, folks. Although the Second Amendment people, maybe there is, I don't know," the braggadocious builder told a North Carolina crowd on August 10.

Naturally, Trump said what he really meant was that gun owners could use their unparalleled organizing skills to convince the Senate to obstruct Clinton's nominees, or even prevent her from ever reaching the Oval Office at all.

Naturally.