Just like any shrewd businessman, Donald Trump knows how to make the most of an opportunity.
And last week, when a rare set of circumstances presented the chance to secure more votes come November, Mr Trump didn't hesitate to act on a US Supreme Court nominee.
It might feel distasteful to think about the death of a powerful woman like Ruth Bader Ginsburg leading to such stark political manoeuvrings, but such has become the business of US politics.
And the timing was on Mr Trump's side.
The opportunity to fill a US Supreme Court seat with Amy Coney Barrett allowed Mr Trump to shift the conversation away from the grim milestone of 200,000 coronavirus deaths.
It also allowed him to remind evangelical voters — who, according to polls, are very unimpressed by his handling of the pandemic — why they should stick with him in November.
But a report from the New York Times detailing allegations about Mr Trump's tax returns may be where his luck runs out.
And this week the timing, coming just two days before Mr Trump's first debate with Joe Biden and five weeks before the election, is against him.
Trump might think this won't change anything
If the reporting is true, the details are potentially very damaging to Mr Trump: he paid no federal income taxes in 10 of the past 15 years, he paid just $US750 ($1,064) in taxes in 2016 when he was elected, he effectively erased his tax bill by reporting heavy losses across his business interests and also claimed up to $US70,000 in hairstyling expenses.
But is it enough to change voters' feelings about the President?
It was only four years ago that Mr Trump remarked: "I could stand in the middle of Fifth Avenue and shoot somebody, and I wouldn't lose any voters, OK?"
If we were to take Mr Trump at his past statements then, at least according to him, this is unlikely to change voters' minds. And he has reason to think he might survive this.
Mr Trump's 2016 campaign also faced explosive allegations, that time over the release of the Access Hollywood tape where Mr Trump was recorded bragging about kissing and groping women without their permission. But he won anyway.
In fact, as The Associated Press reports, polls over the course of Mr Trump's time in office show his support over the years has remained remarkably consistent.
As one writer at the New Yorker put it, "it is probably true, that for many of his supporters, Trump's character — the dishonesty, the bigotry, the incompetence — is a given".
"It's 'baked in,' as the Washington cliche has it. No matter what Trump does, no matter what journalists go on revealing, he has, for the 'base,' delivered on his promise to upend 'the system' and inflame the elites," they wrote.
Will Americans care about this?
Generally, in times of economic growth, Americans are more relaxed about the rich paying low taxes — perhaps optimistic that they too will one day be millionaires.
But these are not optimistic times.
Back in July, two out of three Americans told a Reuters/Ipsos public opinion poll that they wanted to see Mr Trump's income taxes, and about half believed he has been withholding them for reasons that could hurt him politically.
It's clear this is an important issue to some voters.
Part of Mr Trump's success was in winning over blue-collar workers with promises to make their lives great again.
But some have already begun to point out that the image of him painted by these allegations, as a man paying less in taxes than millions of hard-working Americans with less luxurious lifestyles, may be difficult to reconcile with someone who is looking out for them.
"This is an issue that was litigated before the voters in 2016 and the American people elected Donald Trump president of the United States," Trump campaign spokesman Tim Murtaugh told Reuters in July.
That may be the case — these allegations may fail to resonate with voters who have already made up their minds about the President. But many voters haven't made up their minds.
Even before the pandemic, polling showed that two-thirds of Americans strongly believed it was time the super rich paid their share.
With the details now out in the open, and with the promise of more disclosures on the way, there's no telling how this could play out with more than a month to go until the election.
Trump's tax returns have remained an issue for years
In some ways, one would expect Mr Trump's campaign to have prepared itself for something like this. It's not as if his taxes haven't come up before.
Over the past few years, there have been a number of reports on Mr Trump's tax history.
In 2017, MSNBC host Rachel Maddow reported on two pages of Mr Trump's 2005 return that were obtained by investigative reporter David Cay Johnston and released by DCReport.org.
Later that same year, The New York Times reported that Mr Trump had declared a $916 million loss on his 1995 federal tax return, citing three pages of documents from the return.
Mr Trump, however, has spent years dodging questions on the issue.
He has continually refused to show the public his personal tax returns, and even gone so far as to question the public's interest in his taxes.
That's despite a decades-old tradition of financial transparency among presidential contenders.
In response to Monday's reports, Mr Trump said he has "paid many millions of dollars in taxes" but is entitled to depreciation and tax credits.
A lawyer for the Trump Organization, Alan Garten, went a step further and said: "Most, if not all, of the facts [in the report] appear to be inaccurate."
Biden could be key to how Democrats respond
Exactly how this lands may all depend on Mr Biden. He's just been handed a potentially very compelling argument against Mr Trump in time for today's first presidential debate.
It wouldn't be hard for him to use it either, given he has already released several years of financial disclosures and tax returns on his campaign website.
It could also be a warning to Mr Trump. The New York Times reporters appear to have received that paperwork from someone with deep access.
In American presidential politics, they call it the October surprise: the bombshell in the last few weeks of the race that changes everything.
In 2016, it was James Comey's announcement he was reopening the emails investigation.
Mr Trump had hoped his October surprise would be a coronavirus vaccine.
With NYT promising more stories on Mr Trump's business dealings in the weeks to come, he may not get his wish.