Tax troubles threaten Trump as election day nears, and so does his own approach to campaigning

By Cathleen Decker

Oct. 2, 2016 5:10 PM PT

Reporting from Philadelphia — The last weeks of a campaign are about building momentum and finishing strong. That is why the roughest week of Donald Trump’s presidential run, one that worsened with a report that he may not have paid federal income taxes for 18 years due to a nearly billion-dollar business loss, poses a new threat to his candidacy.

The potential damage in the New York Times report, published Saturday night, was threefold. By highlighting a massive financial loss, the report reminds voters that Trump’s business record is checkered, despite his characterizations to the contrary as he vows to apply his business sense to government. It also reminds them that, when it comes to taxes, Trump has played by different rules than those governing most people — and has refused to disclose the results.

And the timing is also dangerous. The newest Trump controversy threatens to dominate the campaign precisely when he and Hillary Clinton should be crafting closing arguments to voters already casting early ballots in some states and preparing to do so in others.

“This week was in many ways a summary of his entire campaign, in that he’s never missed an opportunity to miss an opportunity,” said Republican strategist Kevin Madden, referring to Trump’s habit of diverting attention from his campaign’s desired focus on jobs, change and his opponent’s vulnerabilities.

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Trump already had lost time to make up ground after the first presidential debate by igniting fights about weight with a former beauty queen and making insinuations about Clinton’s marriage.

Now, with just five weeks before election day, he’s likely to use up more time trying to bat back questions about his tax history. The questions are likely to be a focus in Tuesday’s vice presidential debate and next Sunday’s second presidential candidate meeting in St. Louis.

The answers so far seem ill-suited to allaying concerns about Trump among the shrinking number of undecided or third-party voters both Clinton and Trump need in order to win. Chiefly, those are suburban women and young voters who have been reluctant to support either candidate.

Except for one tweet, Trump had no comment Sunday on the New York Times story, which said that a tax loss of $916 million taken in 1995 was enough to offset his personal federal tax liability for 18 years. The exact details of Trump’s finances are unknown because he has declined to release his tax returns — a first for a major-party nominee since the 1970s. The documents on which the Times based its story were incomplete but added previously unknown details.

On Twitter, Trump cast his tax history as a plus. “I know our complex tax laws better than anyone who has ever run for president and am the only one who can fix them,” he tweeted Sunday, adding that the Times was “failing.”

Neither that nor his campaign’s first statement Saturday night denied the gist of the story. Nor did his surrogates, as they fanned out on the Sunday talk shows to defend him and to argue, as Trump had, that he was the candidate best positioned to change the tax system.

“There’s no one who’s shown more genius in their way to maneuver around the tax code,” New Jersey Gov. Chris Christie said on “Fox News Sunday.”

Former New York Mayor Rudolph W. Giuliani used the same word to describe Trump in his defense on NBC’s “Meet the Press.”

“The reality is he’s a genius,” Giuliani said. He compared Trump to figures like Apple founder Steve Jobs and British Prime Minister Winston Churchill in his capacity to bounce back from adversity.

“Great men have big failures,” Giuliani said. “And then they take those failures and they turn them into great results.”

His surrogates insisted Trump had operated within the law. But the threat the matter poses is likely to be political, not legal.

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Trump played into existing concerns among Americans that the wealthy get an unfair break. A 2015 Pew Research poll found that a big majority of Americans aren’t bothered by the taxes they pay. But 6 in 10 said they were bothered “a lot” when wealthy people didn’t pay their fair share.

More than that, the tax issue can contribute to negative views in the minds of voters about a candidate’s character.

The 2012 Republican nominee, Mitt Romney, was reluctant to release his full tax returns, prompting a damaging campaign by Democrats to cast Romney as hiding something and — once he released some documentation — as shirking on paying an appropriate percentage of taxes.

That was part of a broader effort to portray Romney as a corporate deal-maker with little feel for the concerns of the typical American.

Trump, by virtue of his out-sized, television-cultivated personality, has avoided some of the castigation visited on earlier business-oriented candidates. When criticized for, as a donor, being part of a campaign finance system he says he abhors, Trump has cast himself as the insider capable of making change.

But the campaign finance system is a hypothetical to most Americans; not so paying taxes — and feeling resentment toward those who do not.

And more than other Republicans, Trump has made a thrust of his campaign the notion that the nation’s basic infrastructure is in collapse. He has proposed vast government spending — from an unspecified source. But now he risks looking like he has withheld his own funds from support for federal programs.

The tax difficulty may not alter the campaign in a huge way; both he and Clinton are so well-known, and views of them are so firm, that few issues have moved the race dramatically.

But to limit its potential impact, Trump will have to shift the way he has been running for president in the last week, and at periods before that. He will have to make the race about voters, and not about him.

The biggest question that he has to answer, according to polls, is whether he has the judgment and temperament to serve as president. He has, of late, not comported himself in a way that breeds confidence on either score.

In the aftermath of a debate in which he rose repeatedly to take Clinton’s bait, and appeared unprepared as well, Trump has sought to defend what he saw as slights to him, rather than make appeals to voters.

His early morning Twitter rant at former Miss Universe Alicia Machado hit her on weight issues and prompted an endless loop of video showing him shaming her for gaining weight — not exactly the best way to appeal to suburban female voters.

At the same time, he and his allies sought to blame Clinton for her reaction to former President Bill Clinton’s affairs, also not a popular approach among women. He brought up the subject of Bill Clinton’s dalliances on Saturday night during a rambling speech in the rural Pennsylvania town of Manheim.

For Republicans seeking a demonstration of discipline in Trump’s last weeks of campaigning, the speech was a disaster. He called Clinton “crazy” and incompetent. He accused her of cheating on Bill Clinton, without proof. He physically mocked her stumble when she was ill with pneumonia on Sept. 11.

“The issues he’s dealing with aren’t helpful with swing voters,” Madden said. “Undecided voters are not undecided because of Bill Clinton and Hillary Clinton’s marital troubles. And I don’t think they’re persuaded because Trump wins an insult contest with a former Miss Universe.”

Clinton, by contrast, spent Sunday in the electorally important state of North Carolina, attending church and talking about criminal justice issues with the African American voters who could secure a victory for her there.

The first presidential debate provided a fresh start for both candidates, coming as voter attention was growing and balloting was looming. The nominees were in a dead heat; voters were looking to find distinctions that might determine their allegiance.

Since the debate, Clinton has risen in national and statewide polling. Trump’s task has been to try to reverse her gains. Nothing that has happened in recent days stands to accomplish that goal.

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Twitter: @cathleendecker

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