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It happened in late July, when Trump enjoyed a slim national lead only to destroy it with a bizarre convention featuring an angry, ranting acceptance speech followed by a weeks-long smear campaign against Gold Star parents whose son died in Iraq. And it's happening again now.
Trump went into the first debate on Monday once again in a national tie with Clinton and with swing state polls trending in his direction. He needed only a reasonably strong showing in the debate to consolidate his gains and make a play for remaining undecided voters, especially suburban women.
And he blew it in epic fashion.
Trump, who declined rigorous preparation for the debate, failed to go after Clinton on her emails with any vigor and leaped at Clinton's obvious bait by defending his comments about a former Miss Universe's weight gain. And then Trump inexplicably invoked his attacks on Rosie O'Donnell as a "disgusting pig" as something that the TV host "deserved."
Reputable national polls showed Trump lost the debate by a huge margin while Trump and his surrogates clung to unscientific and thoroughly useless internet insta-polls to promote the idea that he "won" the debate. And just like with the Gold Star Khan family, Trump continued to wallow in the Miss Universe story while suggesting he plans to try make former President Bill Clinton's affairs a centerpiece of his campaign strategy.
If you went into a lab to try to design a strategy to repel undecided women from your candidacy, you could not come up with a more perfect result.
Once again on the defensive, Trump launched into an unhinged Twitter rant on Thursday night and Friday morning, completely dispensing with the modicum of restraint exhibited during his rise in the polls over the late summer.
Trump tweeted that Clinton was "duped and used" by former Miss Universe winner Alicia Machado, urging followers to "check out sex tape and past." He went on to refer to Machado as "disgusting" and suggested — without any evidence — that the Clinton campaign may have helped Machado become a U.S. citizen in order to "use her in the debate."
Trump kept up the Twitter assault into Friday morning with posts assailing the media. At 3:20 a.m. he tweeted: "Anytime you see a story about me or my campaign saying 'sources said,' DO NOT believe it. There are no sources, they are just made up lies!"
And at 8:50 a.m.: "Remember, don't believe 'sources said' by the VERY dishonest media. If they don't name the sources, the sources don't exist."
The damage from Trump's disastrous debate and subsequent meltdowns is already starting to pile up. Clinton has moved back to a 3-point advantage in the national polling average. And that figure includes the Los Angeles Times/USC poll that consistently shows a large advantage for Trump that is out of step with all other national polls. The L.A. Times poll relies on a static survey of the same respondents and has other methodological issues that could make it an outlier.
Trump's improvement in state polling is also eroding. The first poll in Florida taken after the debate found Clinton leading Trump by 4 points. Clinton can win the White House without Florida. Trump cannot. If the GOP nominee loses either Florida or Ohio (where he maintains a solid lead), he has no chance of getting to 270 electoral votes.
All of this brings up the question of why Trump is so bent on self-destruction every time he appears poised to possibly win. In the "South Park" view of the election, Trump is actively trying to lose when his Democratic opponent won't allow him to do it. It's possible this is actually what's going on, though if it is, it's probably happening at a subconscious level.
The GOP nominee's behavior at least suggests that deep in his psyche he does not believe that he is prepared for the presidency. And there is probably some truth in the idea that Trump really doesn't want the job as it would so drastically alter his gilded lifestyle.
But the more convincing explanation is just that Trump is so thin-skinned and lacking in self-confidence that he simply cannot let any criticism or attack roll off his back, even if engaging in scorched-earth response is damaging to his political prospects. He could not let go of the Khan criticism and he cannot let go of the Miss Universe issues. There is also a psychological theory underpinning this aspect of Trump's self-sabotage. It's projection.
Trump consistently attacks people for their weight even though he himself is significantly overweight. He attacks the Clinton Foundation even though his own foundation has been shown to be a largely fraudulent organization. He accuses Clinton of running an "unserious" campaign even though his own is perhaps the least serious major party campaign in American history. And now he is going after Bill Clinton's affairs despite his own history of multiple divorces and allegations of infidelity.
Given the fluctuating nature of the 2016 campaign and Hillary Clinton's own myriad weaknesses, there is a good chance Trump could eventually reverse the current trend and make the race close once again. But if he does, history tells us Trump will find a way to blow himself up once more.
—Ben White is Politico's chief economic correspondent and a CNBC contributor. He also authors the daily tip sheet Politico Morning Money [politico.com/morningmoney]. Follow him on Twitter @morningmoneyben.