This story is over 5 years old.

The VICE Guide to the 2016 Election

A Timeline of Donald Trump's Week from Hell

A bizarre debate performance, a feud with a former beauty queen, an unearthed appearance in a Playboy video, allegations of business done with Iran and Cuba, a reported billion-dollar loss, and lots and lots of denials.
Trump speaks in Pennsylvania on October 1. (Photo by Jessica Kourkounis/Getty Images)

Monday, September 26: The first presidential debate between Donald Trump and Hillary Clinton goes rather badly for the Republican nominee. During the course of the debate, he seems to admit not paying federal income tax, interrupts Clinton repeatedly to say "wrong!" over and over again, goes on a bizarre tangent about his ten-year-old son's tech savvy, sniffs a lot, insults Rosie O'Donnell, and earns a big laugh from the audience when he claims he has "better temperament" than Clinton. In typical Trump fashion, though, he brags about the results of a few unscientific online polls showing he "won" the night:


Thank you! Four new — Donald J. Trump (@realDonaldTrump)September 27, 2016

Late Monday: Trump brags about having the class not to bring up Bill Clinton's infidelities during the debate.

Late Monday/early Tuesday: A number of media outlets, including Cosmo and the Guardian, run stories on Alicia Machado, a former Miss Universe who Clinton brought up in the debate. Machado had said in May that Trump called her "Miss Piggy" and "Miss Housekeeping" after she gained weight, but Clinton's bringing up of the story gave it new life.

Tuesday morning: Trump calls into Fox & Friends, which has become his usual forum for addressing breaking news. Instead of expressing any regret about his fat-shaming of Machado, he doubled down, saying, "She was the winner, and she gained a massive amount of weight, and it was a real problem. We had a real problem." The Clinton campaign was already pushing the story to reporters, and Trump seems dead-set on helping them.

Also on Tuesday: Trump continues to claim he won the debate, but also makes excuses for his performance, saying that his mic was defective and that he was "holding back" because he didn't want to "embarrass" Chelsea Clinton, apparently another shot at Bill's affairs.

More from Tuesday: Clinton addresses Trump's complaints to reporters on her plane, saying, "Anyone who complains about his microphone is not having a good night."

"Whoooo!" the reporters say in response.


Sorry, one more from Tuesday: The Arizona Republic endorses Clinton, the first time in the paper's century-plus history it's backed a Democrat for president. "Trump's inability to control himself or be controlled by others represents a real threat to our national security," the editors write. The paper will later receive death threats for the endorsement.

Wednesday: The New York Times runs a story based on interviews with Trump campaign staffers that blames the candidate's lousy performance on a lack of preparation. The staffers told the Times that they wanted to do a better job prepping him for the second debate, but "whether he is open to practicing meticulously is a major concern."

Wednesday night: In what probably felt to Trump like a bit of a break from all this, he gave an interview with a very friendly Bill O'Reilly on Fox News in which he said he "saved" Machado's job, criticized debate moderator Lester Holt, and opined that San Francisco 49ers quarterback Colin Kaepernick's protests were "very bad for the spirit of the country."

By Thursday: The polls echo what nearly the entire media is saying, that Trump looked worse as a result of the debate.

Thursday morning: Newsweek reports that a Trump-controlled company broke the embargo with Cuba in the 90s. Though the statute of limitations on any lawbreaking has expired, it puts Florida's Cuban American leaders—who are generally pro-Republican but also opposed to Cuba's government—in a weird spot.


Also on Thursday: The Detroit News breaks its long tradition of endorsing Republican presidential candidates, instead backing Libertarian Gary Johnson. This isn't because of Johnson's special qualities, the editorial board wrote, but because Trump is "unprincipled, unstable and quite possibly dangerous."

Also on Thursday: The Los Angeles Times reports that employees at a Trump-owned golf course said that Trump wanted to fire unattractive women and generally judged the female employees on their looks.

OK, now, believe it or not, is where things start to go off the rails.

Early Friday morning: Trump goes on Twitter, to, uh, well:

Wow, Crooked Hillary was duped and used by my worst Miss U. Hillary floated her as an 'angel' without checking her past, which is terrible!

— Donald J. Trump (@realDonaldTrump)September 30, 2016

Using Alicia M in the debate as a paragon of virtue just shows that Crooked Hillary suffers from BAD JUDGEMENT! Hillary was set up by a con.

— Donald J. Trump (@realDonaldTrump)September 30, 2016

Did Crooked Hillary help disgusting (check out sex tape and past) Alicia M become a U.S. citizen so she could use her in the debate?

— Donald J. Trump (@realDonaldTrump)September 30, 2016

That "sex tape," by the way, doesn't exist—Trump might have been referring to a bit on a reality show where Machado was filmed supposedly having sex with another contestant. He also might have been referring to nothing. But you know, what does exist?


Friday: BuzzFeed reports on Trump's (fully clothed, thank God) appearance in a softcore Playboy video from 2000.

Also Friday: The Chicago Tribune, yet another normally Republican paper (though it did endorse Barack Obama in '08 and '12) endorses Johnson. Trump "has neither the character nor the prudent disposition for the job" of president, the editors write.

Also Friday: Good news for Trump! The Commission on Presidential Debates, the nonpartisan group in charge of the debates, admits "there were issues regarding Donald Trump's audio that affected the sound level in the debate hall," a short statement that doesn't address the fact that the TV audience could hear Trump just fine.

Also Friday: The Washington Post, which has been doggedly reporting the details and assorted oddities of Trump's charitable foundation, reports that it doesn't have the license required by New York State to solicit funds from donors.

One more from Friday: Trump gives an interview to the New York Times where he doubles down on that whole sex tape thing and hints again that he'll bring up Clinton's marriage as a line of attack. When asked about his own extensively documented history of infidelity, Trump replies, "I wasn't president of the United States. I don't talk about it."

Friday evening: Newt Gingrich, another notorious adulterer who backs Trump, criticizes the candidate, saying, "He's got to become much more disciplined."


Whew. Time to take a break for the weekend, right?

For those few people knocking me for tweeting at three o'clock in the morning, at least you know I will be there, awake, to answer the call!

— Donald J. Trump (@realDonaldTrump)September 30, 2016

Saturday: Leaked audio of Clinton critiquing the idealism of Bernie Sanders's supporters circulates. So at Trump's campaign rally in Pennsylvania on Saturday, he's naturally prepared to make a statement about this new damaging piece of news. But as the Washington Post reported:

"It took Trump nearly 25 minutes to read the brief statement because he kept going off on one angry tangent after another—ignoring his teleprompters and accusing Clinton of not being 'loyal' to her husband, imitating her buckling at a memorial service last month, suggesting that she is 'crazy,' and saying she should be in prison. He urged his mostly white crowd of supporters to go to polling places in 'certain areas' on Election Day to 'watch' the voters there. He also repeatedly complained about having a 'bum mic' at the first presidential debate and wondered if he should have done another season of The Apprentice."

Literally almost at the same time as Trump was rambling about all that: The Times publishes a story on Trump's 1995 tax return, three pages of which were anonymously sent to a reporter. The big takeaway is that he declared more than $900 million in loses, meaning he could likely avoid paying federal income taxes for 18 years. This shows:


A. That Trump (or, more accurately, his accountants) indeed know a lot about the US tax code, which was the candidate's response to the story
B. That the tax code is biased in favor of uber-wealthy people, who are the only ones who can make use of these write-offs
C. That Trump, as a new Clinton campaign ad alleges, "is a business failure who has gotten rich at your expense"
D. That there is stuff just as damaging in Trump's more recent tax returns, which is why he has refused to release them in defiance of political convention
or E. Some combination of the above.

Sunday morning: The tax returns are discussed ad nauseum on the political talk shows. Former New York mayor Rudy Giuliani compares Trump to Steve Jobs and Winston Churchill. New Jersey governor Chris Christie, who is heading up Trump's transition team, calls it a "very good story" that demonstrates "the genius of Donald Trump."

Oh I forgot, sorry: Christie himself is having a bad week, with a former aide in the "Bridgegate" trial detailing how the governor allegedly bought the support of politicians with gifts, including steel from the 9/11 site, and how the governor knew about the plan to close the George Washington Bridge in order to punish a mayor who refused to back Christie.

Melania and I extend our warmest greetings to those observing Rosh Hashanah here in the United States, in Israel, and around the world.

— Donald J. Trump (@realDonaldTrump)October 2, 2016


Monday morning: A report surfaces that a Trump company once leased office space to a terrorism-linked Iranian bank. The campaign didn't answer any questions from the International Consortium of Investigative Journalists about the matter, simply saying, "Mr. Trump's sole focus is and will be on making our country great again."

Also Monday morning: The AP publishes an article quoting members of the cast and crew of The Apprentice claiming that Trump was fixated on the attractiveness of the women on the show and commented so much about a camerawoman that it made people uncomfortable.

Monday: The Times reports that Trump is going to try to change the subject and focus the campaign back on Clinton. His line of attack, according to a spokesman, is that she and her husband are "willing to do anything to make a buck."


Monday afternoon, by which I mean literally the second I am writing this, so by the time you read this something else will have happened: At the rally intended to be a chance for Trump to change the narrative about his lack of self-control, he suggested that soldiers suffering from PTSD "can't handle it."

"There was a silence in the room after his statement," BuzzFeed reported, "and people on social media were quick to express anger toward his comments."

"People on social media were quick to express anger" isn't quite as catchy as "Make American Great Again," but at this point it seems like a more accurate summary of Trump's campaign.

Follow Harry Cheadle on Twitter.