As someone who has written off past business losses against present income, I too have "gamed" the system. But I was about seven magnitudes of order lower than the billionaires class.
Here is another tool the wealthy can use that the average small business person cannot use to write off taxes. Let's assume a wealthy person's accountant deems he ows $10m in taxes. That wealthy person hires a tax lawyer for $1m to find an interpretation of the tax code such that no taxes are owed.
So the wealthy person and tax man end up in civil court, which takes 5 to 10 years to bounce around in the court system. The tax man fears the judgement goes for the wealthy person, which then means a legal precedent will be set. When that precedent is set, many more wealthy people will use that precedent to reduce their taxes without much effort. And the tax man collects fewer taxes from the billionaire class. So the wealthy person enter in a negotiation to settle before a judge makes a decision. Maybe $1m in taxes instead of $10m.
I read the original Times articles. Reading between the lines, the Trump Empire is about to fall anyways: too many business units are being supported by the TRUMP brand name. But it also seems that Mr. Trump and tax man are not negotiating a deal either. Maybe the tax violations are so apparent that the tax feels he can't lose. But we should not rule out that Mr. Trump lack of vision for this negotiation either.