50 Moments That Defined the 2016 Election Cycle

It’s been a long, hard-fought battle and there’s finally light at the end of the tunnel.

Illustration by Elizabeth Brockway/The Daily Beast

On Tuesday, Americans will cast their ballots in the 2016 presidential election after a wild 19-month ride. Both sides underwent bitter primary battles, and those who emerged victorious are two of the most unpopular presidential nominees in modern history.

The 24-hour news cycle often makes us easily forget what happened last month, last week, or even yesterday. So here are 50 key moments that turned the 2016 election upside down, starting with the day Donald Trump officially entered the race.


June 16, 2015 — Donald Trump Enters the Race

Donald Trump officially announced his candidacy for president on June 16, 2015. In his speech, he suggested that some Mexican immigrants were rapists and drug dealers—a line that the Hillary Clinton campaign has never quite let die.

Late June 2015 — NBC, Brands Drop Trump over Mexican Comments

Trump’s comments about Mexicans caused a firestorm of rebukes, notably from NBC, which dropped the Trump-owned Miss Universe and Miss USA pageants. Other brands followed suit, including Macy’s, NASCAR and the PGA Tour.

July 18, 2015 — Trump: John McCain Not a War Hero

Trump went on the attack against Arizona Republican Sen. John McCain, suggesting he is not a war hero because he was captured and held for five years as a prisoner of war in Vietnam.

July 27, 2015 — Trump’s Ex-Wife: He Made Me Feel “Violated” During Sex

The Daily Beast’s Tim Mak and Brandy Zadrozny exclusively reported last July that Trump’s ex-wife Ivana once use the word “rape” to describe an incident between the two in 1989.

Aug. 6, 2015 — Megyn Kelly, Trump Tussle at First Debate

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Fox News host Megyn Kelly kicked off the first Republican primary debate last August by confronting Trump about his derogatory comments about women over the years, initiating Trump’s months-long feud with Kelly.

Aug. 6, 2015 — Trump Doesn’t Rule Out Third-Party Run

When Trump was considered to be a long-shot for the GOP nomination early on, he refused to say that he wouldn’t run as an independent candidate should he lose the GOP primary.

Aug. 7, 2015 — Trump on Megyn Kelly: ‘Blood Coming Out of Her Wherever”

The day after the first debate, Trump went on the attack against Kelly, suggesting that she asked the question because she was menstruating. “You could see there was blood coming out of her eyes, blood coming out of her wherever, but she was, in my opinion, off-base,” Trump said on CNN.

Sept. 9, 2015 — Trump on Carly Fiorina: ‘Look at That Face’

Last September, Trump made disparaging remarks about rival Carly Fiorina’s looks. “Look at that face! Would anyone vote for that?” Trump said in an interview with Rolling Stone.

Oct. 13, 2015 — Bernie on Hillary’s ‘Damn Emails’

In a Democratic primary debate last year, Bernie Sanders defended Clinton against a barrage of attacks and lines of questioning she was receiving over her exclusive use of a private email server while she served as secretary of state. “The American people are sick and tired of hearing about your damn emails,” Sanders said. “Enough of the emails!”

Oct. 22, 2016 — Hillary’s Marathon Benghazi Hearing

Last October, Clinton testified for a marathon 11 hours in front of the House Benghazi Committee.

Dec. 2, 2015 — Trump: Kill Terrorists’ Families

Six months into his presidential campaign, Trump called for the killing of terrorists’ families as an effective way to defeat ISIS. “You have to take out their families,” Trump said during a TV appearance. “When you get these terrorists, you have to take out their families.”

Dec. 7, 2015 — Trump Proposes Muslim Ban

After the terror attack last December in San Bernardino, California, Trump proposed a “total and complete shutdown of Muslims entering the United States until our country’s representatives can figure out what is going on.”

Jan. 23, 2016 — Trump: I Could Shoot Someone and Not Lose Votes

Trump joked with supporters at a rally that he could “stand in the middle of 5th Avenue and shoot someone, and I wouldn’t lose any voters.” It was an effort to convey how loyal they are to him.

Feb. 1, 2016 — Ted Cruz Wins Iowa Caucus

Ted Cruz defeated Trump in the Iowa caucus, the first contest in the 2016 presidential primaries. The surprise victory temporarily halted Trump’s momentum, as he had been polling at the top of the GOP pack for months.

Feb. 3, 2016 — Jeb: ‘Please Clap’

It was a moment that previewed the downfall of Jeb Bush’s presidential campaign; at a town hall event in New Hampshire, Bush awkwardly asked the audience to clap after he concluded his statement.

Feb. 18, 2016 — Pope Francis Rebukes Trump

Pope Francis delivered a strong rebuke of Trump, calling him out over his “un-Christian” immigration policies. “A person who thinks only about building walls, wherever they may be, and not of building bridges, is not Christian,” the pontiff said. “This is not the gospel.”

Feb. 20, 2016 — Jeb Drops Out

Once considered the overwhelming frontrunner for the GOP nomination, former Florida Gov. Bush dropped out of the race in February after a poor showing in the South Carolina primary.

Feb. 24, 2016 — Romney: ‘Bombshell’ in Trump’s Taxes

Mitt Romney, the 2012 Republican presidential nominee, has made his disdain for Trump well known, at one point suggesting that there was a “bombshell” in his tax returns that has been preventing him from making them public.

Feb. 6, 2016 — ‘Robot Rubio’

New Jersey governor Chris Christie went after Marco Rubio at a Republican presidential debate in February after the Florida senator kept repeating a line about President Obama. “There it is. There it is,” Christie said at one point to throw Rubio off guard. “The memorized 25-second speech.” This debate created the “robot Rubio” meme.

Feb. 8, 2016 — Trump Repeats Fan: Cruz a ‘Pussy’

At a rally in New Hampshire on the eve of the state’s primary, Trump repeated a supporter in the audience who shouted that Cruz was a “pussy.” Trump jokingly said he hope to never “hear that from you again… That’s terrible.”

Feb. 26, 2016 — Trump Suggests ‘Opening Up’ Libel Laws

At a rally in late February, Trump said he wants to “open up our libel laws” so that he could more easily sue news organizations whose reporting he doesn’t like. “So when The New York Times writes a hit piece which is a total disgrace or when The Washington Post, which is there for other reasons, writes a hit piece, we can sue them and win money instead of having no chance because they’re totally protected,” he said.

March 3, 2016 — Trump Brags About His Genitalia

During a Republican primary debate in March, Trump bragged about the size of his genitalia after Rubio jabbed at him about his hands. “And he referred to my hands, if they are small, something else must be small,” Trump quipped. “I guarantee you there’s no problem, I guarantee you.”

March 22, 2016 — Trump Threatens Cruz’s Wife

Trump threatened to “spill the beans” on Cruz’s wife, Heidi Cruz, after an anti-Trump super PAC ran an ad mocking Melania Trump’s nude appearance in GQ Magazine.

March 31, 2016 — Violence Intensifies at Trump Rallies

Trump’s campaign rallies often become violent when protesters clash with supporters, and Trump himself has sometimes egged his supporters on. He once said he would pay for the legal fees of someone who punched a protester.

May 3, 2016 — Trump Pushes Rafael Cruz-JFK Assassination Connection

Trump pushed a tabloid story about Ted Cruz’s father, Rafael, connecting him to the assassination of President John F. Kennedy.

May 3, 2016 — Trump Wins Indiana, Becomes Presumptive GOP Nominee

Trump defeated Cruz in the Indiana primary, cementing himself as the GOP’s presumptive presidential nominee. Cruz immediately dropped out of the race.

June 6, 2016 — Hillary Becomes Presumptive Nominee

She had to wait a little bit longer than Trump to defeat her last-standing rival, but Clinton became the presumptive Democratic nominee on June 6.

June 7, 2016 — Trump vs. Judge Curiel

For months, Trump attacked a federal judge, Gonzalo Curiel, over his Mexican heritage. Trump said Curiel, who is an American citizen, couldn’t properly preside over his Trump University fraud case because he is “a Mexican” and “we’re building a wall between here and Mexico.”

June 17, 2016 — Rubio Announces Senate Re-Election Bid

Despite saying he would not run for re-election regardless of how he fares in his presidential run, Rubio announced in June that he would make a bid to keep his job in the Senate.

July 5, 2016 — FBI Declines to Recommend Charges over Email Server

In July, FBI Director James Comey announced that his agency would not recommend criminal charges against Clinton for her exclusive use of a private email server while she served as secretary of state. Comey, however, said the decision to use the private system was “extremely careless.”

July 19, 2016 — Melania Trump Plagiarizes Michelle Obama

Melania Trump, the third, and current, wife of the GOP nominee, was caught plagiarizing excerpts of her speech at the Republican convention in Cleveland. Many of the lines were lifted from Michelle Obama’s speech at the Democratic convention in 2008.

July 20, 2016 — Cruz Refuses to Endorse Trump at Convention

During his speech at the Republican National Convention in Cleveland this summer, Cruz was booed by the crowd for not explicitly endorsing Trump. The two were locked in a bitter primary battle until the very end, and traded insults almost daily.

July 24, 2016 — Wasserman Schultz Steps Down

Just a day before the Democratic convention began, embattled DNC Chair Debbie Wasserman Schultz announced should would step down after the convention and give herself a reduced—or practically non-existent—role at the four-day-long event in Philadelphia. Her resignation came after WikiLeaks released hacked DNC emails which showed a bias against Sanders.

July 30, 2016 — Trump Defames Khan Family

Trump pushed back against Khizr Khan’s emotional attack on him at the Democratic convention, telling ABC News that he has “made a lot of sacrifices,” and suggesting that Khan’s wife, Ghazala, was not “allowed” to speak at the convention. The Khans lost their son, a U.S. Army captain, in Iraq in 2004. As recently as two weeks ago, Trump said Humayun Khan would still be alive if he had been president at the time.

August 8, 2016 — Evan McMullin Jumps In the Race

In early August, conservative candidate Evan McMullin entered the presidential race, hoping to present himself as a conservative alternative to Trump. Although he is only on the ballot in a few states, McMullin has been surging in his native Utah, and could derail Trump’s chances of winning 270 electoral votes if he pulls off a victory there.

August 9, 2016 — Trump on ‘Second Amendment People’

Trump once suggested at a rally that “Second Amendment people” could spring into action if Clinton is granted the opportunity to appoint justices to the Supreme Court. The remark was widely viewed as a threat, but Trump downplayed that characterization.

Sept. 8, 2016 — Gary Johnson’s Aleppo Gaffe

Libertarian presidential nominee Gary Johnson was dumbfounded when asked on MSNBC about Aleppo, the besieged Syrian town that has been the center of that country’s civil war. When asked what he would do about it, Johnson replied: “And what is Aleppo?” Johnson was consistently polling in double digits before the “Aleppo moment,” and dropped off into the mid-single digits shortly afterward.

Sept. 14, 2016 — Flint Pastor Shuts Down Trump

Immediately after he began attacking Clinton while addressing a church crowd in Flint, Michigan, Trump was interrupted by the pastor who rebuked him for getting political. “Mr. Trump, I invited you here to thank us for what we’ve done in Flint, not give a political speech,” Rev. Faith Green Timmons told him.

Sept. 19, 2016 — Trump Ends Birther Crusade

Trump ended his years-long birther crusade against President Obama in September when he declared for the first time that Obama was born in the United States, “period.” He did not apologize for propagating the myth for so long, and falsely claimed that Clinton’s 2008 presidential campaign started the rumor about Obama’s birthplace.

Sept. 22, 2016 — House Committee Holds Hillary’s IT Manager in Contempt

The House Oversight and Government Reform Committee voted in September to hold Bryan Pagliano, Clinton’s former director of IT, in contempt of Congress for refusing to testify about his role in maintaining Clinton’s private email server.

Sept. 23, 2016 — Cruz Endorses Trump

Just two months after he was booed off the stage at the GOP convention for refusing to endorse the party’s standard-bearerd Cruz finally came around, despite sharp differences and a rocky history with the GOP nominee.

Late September 2016 — Trump Attacks Alicia Machado

At the first presidential debate, Clinton mentioned Trump’s denigration of a former Miss Universe winner, Alicia Machado, and Trump and his surrogates kept the controversy alive for days by smearing Machado, even saying she became overweight.

Sept. 28, 2016 — Gary Johnson Can’t Name a Foreign Leader

During an interview on MSNBC, Libertarian presidential nominee Gary Johnson was unable to name his favorite foreign leader. “I guess I’m having an Aleppo moment,” Johnson said, referring to when he admitted to not knowing the name of the Syrian city most affected by the civil war.

Oct. 1, 2016 — New York Times Bombshell on Trump’s Taxes

In early October, the New York Times obtained some of Trump’s tax records, which showed that he could have legally avoided paying taxes for nearly two decades. In the second presidential debate, Trump basically admitted to using the loophole.

Oct. 7, 2016 — Access Hollywood Tape Leaks

The first of many “October surprises” was when The Washington Post released a tape of Trump in which he bragged about using his stardom to sexually assault women. The release of the tape was dubbed by The Daily Beast’s John Avlon as the moment that lost Trump the election.

Oct. 7, 2016 — First WikiLeaks Dump

WikiLeaks announced that it had obtained the hacked emails of Clinton campaign chairman John Podesta. Daily disclosures have revealed the inner workings of the Clinton campaign as well as Podesta’s personal connections dating back to Clinton’s failed 2008 presidential bid.

Oct. 19, 2016 — Trump Calls Hillary a ‘Nasty Woman’

During the third and final presidential debate, Trump calle Clinton a “nasty woman.” The insult backfired, though, as female Clinton supporters took to social media to proudly declare themselves “nasty women” and rally others behind Clinton.

Oct. 19, 2016 — Trump Won’t Say He’ll Accept Election Outcome

When asked whether he would concede to Clinton if he loses the election, Trump said he will “tell you at the time” and “keep you in suspense.” Clinton said Trump was essentially “denigrating and talking down our democracy.”

Oct. 28, 2016 — Comey Sends Vague Letter over Newly Discovered Clinton Emails

Just 11 days before Election Day, FBI Director James Comey sent a vague letter to members of Congress in which he said that more emails had been recovered relating to Clinton’s private email server. The emails are believed to have been recovered from a computer owned by Clinton aide Huma Abedin and her estranged husband, Anthony Weiner, who is under investigation for allegedly sexting with a 15-year-old girl.

Nov. 6, 2016 — Comey Sends New Letter, Clears Hillary

Just nine days later—and two days before the election—Comey sent another letter to members of Congress in which he said upon review, the agency found nothing in the emails recovered on Weiner’s laptop that would necessitate a recommendation for criminal charges to be brought against Clinton.

Additional reporting by Amelia Warshaw and Peter Slattery