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Unfortunately for Trump, though, it's a pretty safe bet to label this last week the worst of the three.
The trouble started last Monday when the Republican nominee struggled to fend off a slew of attacks from his Democratic opponent, Hillary Clinton, at the first presidential debate.
Trump's performance, viewed by more than 84 million people, was widely panned by analysts and politicians on both sides of the political aisle.
And every poll and focus group conducted in the aftermath of the Hofstra University duel arrived at the same conclusion, finding that Hillary Clinton bested the real-estate tycoon by large margins.
But the damage was only just beginning.
Leaks began to emerge from the Manhattan billionaire's campaign in the aftermath of the debate. Campaign sources told reporters they were disappointed in Trump's preparation for the political slugfest, embarrassing the brash billionaire who was insistent that he had emerged as the winner.
Trump, frustrated his staffers were talking to the press, worked to delegitimize the leaks, saying that supporters should not trust information pegged to anonymous sources.
At the same time, Trump and top surrogates began doubling-down on his decades-old comments about former Miss Universe winner Alicia Machado, who Clinton brought up toward the end of the first debate. Trump had humiliated Machado, from Venezuela, for gaining weight at the time. She said he referred to her by demeaning nicknames like "Miss Piggy" and "Miss Housekeeping."
In the apex of the renewed feud with Machado, Trump fired off a series of scathing tweets in the wee-hours of Friday morning, calling Machado "disgusting" and asking his followers to "check out sex tape and past."
Machado did have an appearance in a Spanish-language reality TV program where she appeared to engage in sexual activity in bed with a fellow cast-mate. Trump's campaign further pointed to foreign press reports that Machado was a murder accomplice, which she did not deny in an interview with CNN.
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That was followed up by a disastrous Saturday.
The New York Times published three pages of his tax returns from 1995 - obtained via an anonymous mailing to the reporter - that showed Trump claimed a more than $900 million loss that year, which tax experts said would have made it possible for him to not pay any federal income taxes for two decades.
Trump's campaign neither confirmed or denied the accuracy of the report. Instead, a campaign statement ripped the Times for "illegally" publishing the returns and praised Trump for intelligently using the tax code to his advantage, a line that Trump's surrogates repeated in the following day.
Just as the Times report was being released, Trump, during a rally in Pennsylvania, both asserted that Clinton might have cheated on her husband and reenacted the former secretary of state's health episode from early September, when she appeared to collapse as she was entering her car.
"Hillary Clinton's only loyalty is to her financial contributors and to herself," Trump said. "I don't even think she's loyal to Bill, if you want to know the truth. ... And really, folks, really, why should she be? Right? Why should she be?"
Trump's imitation of Clinton with pneumonia. pic.twitter.com/ciqvMW3l0G
- T. Becket Adams (@BecketAdams) October 2, 2016
He later added that "she can't make it 15 feet to her car" before flailing his arms and unsteadily walking away from the podium as if he were about to collapse.
To cap it all off, Forbes downgraded Trump's net worth by $800 million.
"What we're seeing is somebody who's blowing himself apart in real time," Peter Wehner, who served in the administrations of the last three Republican presidents and who opposes Trump, told The Washington Post. "It's a pretty extraordinary thing to see. It's a political death wish, as if at some deep level he doesn't want to be president."
"It's gnawing on him that he could become what he has contempt for, and that is a loser," he added.
REUTERS/Lucas Jackson
Trump was also hit with a swath of sagging post-debate poll numbers. He dipped further behind Clinton in the RealClearPolitics two-way and four-way polling averages. His odds of winning in November fell nearly 10% in renowned statistician Nate Silver's "polls-plus" forecast in the days that followed the debate.
"Political operatives and strategists are going to study this week for generations as the textbook case of self-sabotage," Mo Elleithee, a Democratic strategist who runs Georgetown University's Institute of
Despite the not-so-good week, there was still hope for Trump.
The real-estate tycoon has recovered from similar disastrous weeks in the past, bringing himself back to a near-even level in the polls. Moreover, this time around, unlike the prior times he's come off poor weeks, his poll numbers have not collapsed quite as hard.
And, Trump has two chances this week to rebound from the disastrous week.
On Tuesday, Trump's running mate, Mike Pence, will debate Clinton's running mate, Tim Kaine, in the vice presidential debate. In 2012, after President Barack Obama was widely viewed to have lost the initial debate to Republican nominee Mitt Romney, Vice President Joe Biden helped to build him some momentum during his debate against Romney's running mate Paul Ryan.
Then, on Sunday, Trump gets his second chance to face off with Clinton - this time in a town hall setting.
His rebound will likely be closely tied to the level of preparation he puts into his effort ahead of that debate. He has six days to get ready.