With 36 days remaining before Election Day, the real estate mogul's campaign is consumed with the fallout from a New York Times story
published over the weekend that found Trump reported a $916 million loss in 1995. That loss could mean Trump went 18 years without paying federal income taxes.
Those findings -- which Trump's campaign isn't disputing but haven't been independently confirmed by CNN -- would be daunting for any presidential candidate to overcome. But they're especially challenging for Trump, who is losing control of the campaign's narrative after a strong September in which he narrowed the race with Hillary Clinton.
In just the past week, Trump delivered an underwhelming debate performance, struggled to recover from it, engaged in a counterproductive feud with a Latina beauty queen, posted early morning Twitter tirades and spewed insinuations without any evidence about Clinton's marriage. The tax story -- which could undermine Trump's image as a successful businessman -- will dominate the next few days.
Time is dwindling for Trump to regain his grip on the campaign's message as Clinton supporters seize on the drama to reinforce their point that he isn't suitable for the presidency.
"The reality is that we are in day six of the meltdown," Clinton supporter Neera Tanden said Sunday on CNN's "State of the Union." "He had a terrible debate performance. Everybody sees that. He sees the state polls moving towards Hillary. Eleven state polls were out this week. She's beating him in every single one. He can't take that. And so this is the latest meltdown."
Of course, the tax story might not emerge as the kind of October surprise-style impact that Democrats hope. It is possible that Trump truly is a Teflon candidate who is so appealing to voters that his actions don't really matter. The GOP nominee's closest surrogates launched a fierce defense of Trump Sunday, portraying him as a master of business who expertly used the tax code to his benefit -- and that of his investors.
In a spirited showdown with CNN's Jake Tapper on "State of the Union," former New York Mayor Rudy Giuliani hailed Trump as a "genius."
"He knows how to operate the tax code for the benefit of the people he's serving," Giuliani said.
Speaking on "Fox News Sunday," New Jersey Gov. Chris Christie dismissed the idea that Trump had done anything wrong or that the report would hurt him.
"This is actually a very, very good story for Donald Trump," Christie said.
The impact of the story -- and the swirling controversies that have bubbled up over the past week -- will come into greater focus Monday as Trump returns to the campaign trail in the key swing states of Virginia and Colorado.
He largely stuck to the script at the first event of the day in which he discussed cybersecurity. But he stumbled during a question and answer session when he suggested that American soldiers and veterans who commit suicide do so because they can't handle the post-traumatic stress of war.
"When you talk about the mental health problems, when people come back from war and combat and they see things that maybe a lot of folks in this room have seen many times over and you're strong and you can handle it but a lot of people can't handle it. They see horror stories, they see events you couldn't see in a movie, nobody would believe it," Trump said during a panel interview
at the Retired American Warriors PAC, in Herndon, Virginia.
The tax issue will almost certainly play a significant role in Tuesday's vice presidential debate. If that's the case, it will be a lost opportunity for Trump's running mate, Mike Pence, to present himself to the country as a moderating force on the GOP nominee and someone who can offer a coherent case against a Clinton presidency.
And ahead of the next presidential debate on Sunday, there's no sign Trump will do something to address the lack of focus, preparation and impulse control that helped contribute to Clinton's win at last week's showdown. Trump is now vowing to be nastier than Clinton at the second debate, bringing up Bill Clinton's marital indiscretions. At a wild rally on Saturday night, he even questioned whether Hillary Clinton had been "loyal" to her husband.
Such rhetoric not only calls into question Trump's strategy, it lets Clinton slide on some of her most significant vulnerabilities, such as her email server and questions of trust and honesty.
Trump's approach, and refusal to ignore a trap laid by Clinton in the first debate over his treatment of former Miss Universe contestant Alicia Machado, raises doubt over whether he can make inroads with educated women voters who could be vital to claim must-win states like Pennsylvania.
The freewheeling Trump on display in recent days is particularly notable because he had been doing so well and appeared keen to project more discipline under his retooled campaign team. The GOP nominee effectively wiped out Clinton's lead in national polls after an effective spell through August and mid-September. He was beginning to match her in swing states on the electoral map.
Then, after an encouraging first 30 minutes of the debate, it all went downhill. Trump has not allowed himself to get back on message ever since.
"What happened to him was he was doing well," said Van Jones, a Democrat who is supporting Hillary Clinton, on "State of the Union." "I was terrified 10 days ago this guy was going to be able to be disciplined. Hillary Clinton in 15 minutes said two or three things and threw him off his game and he has not been able to recover since the debate."
Trump's Rust Belt route
The GOP nominee's only route to the White House lies in running the table through the Rust Belt from Pennsylvania, through Ohio, Michigan and Wisconsin. That's why the tax story could prove powerful if struggling blue collar workers disaffected with the Democrats and considering Trump are alienated by the revelation -- even if everything was perfectly legal.
The tax issue also allows Democrats to reclaim the narrative about economic equality and fairness that proved so powerful for President Barack Obama against Republican nominee Mitt Romney in 2012. Clinton's primary rival, Bernie Sanders, relished the chance to make that point
"So, you have got the middle-class people working longer hours for low wages. They pay their taxes. They support their schools. They support their infrastructure. They support the military. But the billionaires, no, they don't have to do that, because they have their friends on Capitol Hill. They pay zero in taxes," Sanders said on "State of the Union." "So, Trump goes around and says, 'hey, I'm worth billions, I'm a successful businessman, but I don't pay any taxes. But, you, you make 15 bucks an hour, you pay the taxes, not me.'"
He added: "That's why people are angry and want real change in this country."