Trump Doesn’t Propose Closing the Loopholes He Exploited

It’s a major flaw in his ‘only someone who games the system can fix it’ argument.


Donald Trump often says that because he’s gamed the system he knows how to fix it. We make fun of that argument but it’s actually a pretty good line. If you want to shore up the security problems in your computer system, you might well hire a former hacker.

There’s one small problem: Trump never actually says how he would deploy this insider knowledge to fix the problems.

Let’s start with taxes. Trump’s response to the New York Times revelations that he may not have paid taxes for 18 years was to tweet:

Chris Chritie agreed: “What it shows is what an absolute mess the federal tax code is and that’s why Donald Trump is the best person to fix it.”

But taxes are one area where Trump has actually put out a detailed plan.  Get  this: He does not touch the carried losses provision that allowed him to use massive business losses to eliminate his personal tax liability.  According to the Times piece, Trump took advantage of a part of the code that allows investment losses to wipe out personal tax liabilities, not just for that year but for future years.  His plan allows that practice to continue — and may make it worse by reducing the tax rade for “pass through” income (that passes through from business to personal returns).

Hillary Clinton’s plan would appear to eliminate the practice, indirectly, by establishing a larger minimum tax on people with substantial income (a.k.a. the Buffett Rule).

The second area where Trump makes the only-a-former-criminal-can-solve-crime argument is money and politics. Throughout the primaries he said that since he’s bought and sold politicians he knows exactly how to fix the system. But here again, he has not said how or really even if he would use this real-world-wisdom to make things better.

He has vaguely said he supports campaign finance reform but has no campaign finance proposal on his website. He denounced super PACs during the primary  but not during the general election (during which he has received much support from pro-Trump super PACs). He has not said if he wants the Citizens United Supreme Court decision overturned but hired as his deputy campaign manager the person who ran…. Citizens United.

His most effective pitch about money and politics during the primaries was to self-fund. Two big problems there. Unless he’s saying that only people who can self-fund should run for office, then that’s not actually a policy that fixes the system. And he ditched that approach for the general election and now actively raises money from mega-donors.

Imagine how much more powerful Trump’s pitch would have been if he’d followed up the “I gamed the system so I can fix it” schtick with dramatic proposals to actually repair the problems. I wonder whether his failure to do so reflects cynicism or just laziness.

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Steven Waldman is founder of, a platform for online memorials and life milestones. He's a Washington Monthly contributing editor, journalist and author.