WASHINGTON — President Donald Trump told the tax man he was the country’s biggest loser, according to Internal Revenue Service filings obtained by The New York Times, and that will make it harder for him to win re-election.

The vast majority of his base voters won’t care whether he paid taxes or lied about being a successful businessman. His ability to pull one over on the public or the government — perhaps both — will be accepted by most of his supporters as evidence of his cunning, his acumen and his strategic brilliance.

But that base is simultaneously Trump’s greatest strength and weakness on the electoral battlefield.

His inability to expand beyond his base and court the less strident is the main challenge to his re-election hopes. And the tax records make things worse. The documents reinforce narratives about Trump that fire up Democrats and give pause to Republican-leaning voters who might be persuaded either to cast ballots for Democratic nominee Joe Biden or simply stay home.

The tax payment numbers are empirical evidence of his long history of duplicity on his business record. They show that most of his ventures, save for branding himself as a big-swinging CEO, have been abject failures.

That evidence comes on the heels of Trump’s acknowledgment that he played down the threat of the coronavirus, which has claimed more than 200,000 American lives and millions of jobs, and the possibility that he paid less than he owed in taxes gives lift to the charge that he doesn’t understand the concept of sacrifice.

Now, on the eve of the first presidential debate, Trump must choose: tell the American public that his tax filings were bogus or admit that he isn’t the heavy-hitting CEO he says is. His attempt so far — to write the report off as “fake news” — is unlikely to carry weight with the most critical voters.

That puts him on the defensive about whether he is honest and trustworthy. That isn’t a fight Trump wants to wage.

Fewer Americans believe Trump is honest and trustworthy than Biden. And Trump finds himself battling over that ground yet again.

Fighting the pandemic required honesty to convince the public to make health and economic decisions based on the information from the government. Trump was most responsible for providing accurate information that allowed people to act in their own best interests and those of their families and friends.

Lives and livelihoods were lost when people misjudged the peril.

On Monday, NBC News’ Monica Alba reported that Dr. Robert Redfield, the head of the Centers for Disease Control and Prevention, said in a private phone call that Trump is misleading Americans about the status of coronavirus because he is being armed with misinformation from Dr. Scott Atlas, a new adviser on the pandemic.

“Everything he says is false,” Redfield said of Atlas while talking on the phone on a commercial airliner, Alba reported.

It’s hard enough to win over new voters for a candidate who is on offense; it’s nearly impossible when that candidate is playing defense.

So while the tax records don’t contain many surprises for those who have paid close attention to Trump’s business dealings — and the distance between his boasts and the reality of his record as the head of the firms that make up “Trump Inc.” — they do put Trump in a position he would like to have avoided.

The tax documents cover more than two decades, including some of his time as president, but they do not include his returns from 2018 and 2019. NBC News has not seen or verified any of the documents reported by The Times.

At a time when Trump should be able to use the Supreme Court nomination of Amy Coney Barrett to focus the voting public on a topic he likes — his judicial appointments — he will be forced to address the particulars of his tax filings. They run counter to his own narrative that he is applying skills learned in the business world to promote prosperity for the American people.

In most years, he paid nothing in individual federal income taxes. In good financial years, he plunked down $750.

For the hardest-core members of his political base, that’s evidence that he was winning.

For the voters he needs to push to mobilize and for those he needs to swing his way, it is likely to raise more doubts about his integrity. That won’t help him win the presidency.

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