Hillary Finds Her Trump Card

Tax.

That was it.

Tax!

It’s hard to believe after months of debate, countless millions of words written about the gnarly character of the man, that Donald J Trump’s weakness might prove to be one that is so classically American. It was tax, of course, that finally saw the end of some of America’s most notorious tough guys: Al Capone, Wesley Snipes, Martha Stewart… For Trump, however, we might have expected something more exotic: trysting on the back of a gold plated toboggan with a Miss World contestant or being sucked into the jalapeño inlet vent of a secret pipeline pumping spicy salsa straight from Mexico. But no. It was tax or, specifically, the subject of Trump’s tax returns that tripped him during Monday’s presidential debate.

The significance has yet to achieve much traction in the media but don’t expect this to last. The question of tax hurt Trump and it will continue to inflict pain. Whether the American public will care is another matter. To some, it will prove that he has street smarts, whilst also setting him against the federal government, which many on the right will find appealing. It’s among the undecided moderates where tax could well force their decision and become a problem to The Donald. The coming days and weeks will be interesting to see if Trump responds. The hardest political decisions are often based on potential damage. If Trump doesn’t release his tax returns, we can assume that they contain something even more damaging than the current suggestions of tax avoidance.

What this also proves is that Trump’s biggest danger continues to be his willingness to shoot from the hip. It’s a problem for a man who can be easily riled on certain topics. His relationship with his father appears to be a significant point of weakness. Democratic strategists might want to hire a few psychologists to explore it further. Why does Trump get sore when pressed on his background?

It’s not the first time that Trump has been seen to be twitchy about his paterfamilias. He famously tried to sue Bill Maher when the comedian suggested that Trump father was an orang-utan. Trump has also claimed to have built a fortune from next to nothing but, when Clinton suggested that he was helped by a fourteen million dollar loan from his father, the billionaire visibly bristled. It’s a slight he seems psychologically incapable of letting pass without comment. He described it as a ‘very small loan’ but it was clear that the damage was done. Once Clinton has pushed that button, Trump unfolded over the course of the subsequent hour as Clinton baited him.

So you’ve got to ask yourself, why won’t he release his tax returns? And I think there may be a couple of reasons. First, maybe he’s not as rich as he says he is. Second, maybe he’s not as charitable as he claims to be. […] Or maybe he doesn’t want the American people, all of you watching tonight, to know that he’s paid nothing in federal taxes, because the only years that anybody’s ever seen were a couple of years when he had to turn them over to state authorities when he was trying to get a casino license, and they showed he didn’t pay any federal income tax.

Trump should had remained calm. He should have stayed on script. Instead, he did what Trump always does. He bit back with an instinct quip that, perhaps, he had not had time to think through.

‘That makes me smart’ he said, leaning down to the microphone as he tends to do when interjecting.

It was not smart. It was, in fact, as far from smart as stupidity gets. He then compounded his error moments later when he seemed to confirm that he pays no federal tax. ‘It would be squandered, too, believe me.’

Again, to some, these lines might work but Trump is past the point where he needs to be appealing to his core voters. In the middle ground, where people still harbour big doubts about Hillary, these admissions might not play well for those considering voting for Trump. It’s hard to see his quips in the context of a considered strategy.

Clinton then pressed him on his dealings with small businesses and his reputation for not paying. Again, Trump could not let the insult slide. Speaking about one contractor, he said: ‘Maybe he didn’t do a good job and I was unsatisfied with his work.’

He has the right to do that. We’ve even had chance to see it firsthand during the campaign. ‘Don’t pay the son of a bitch’ he shouted during a rally in Florida back in January. ‘This mic is terrible, stupid mic keeps popping… Don’t pay him. You know I believe in paying but when somebody does a bad job like this you shouldn’t pay the bastard. Terrible! Terrible!’

He had a point and perhaps he always had a point. More of us should complain when service is poor. The problem is that we don’t know whether Trump is demanding or simply cheap and, even if it is the former, we can reasonably doubt it given the weight of the evidence. By the time Clinton questioned Trump’s use of bankruptcy laws, Trump was incapable of seeing the damage he was doing. ‘I take advantage of the laws of the nation because I’m running a company’ he said. It was not convincing.

The exchange left Trump exposed on a front which had previously been his strongest. Trump’s wealth makes him truly independent. He is not in the pocket of big business. Yet, in the space of a night, all of that was turned around. The allegation that a Presidential candidate might not have paid their taxes would be fatal to any campaign. Tax goes to the very heart of the American president’s power. Every policy involves, in some way, spending taxpayers’ money. That Trump might not have contributed his fair share could hurt him irrevocably. Whether we eventually see them or not, those tax returns might well decide the ultimate fate of the nation.