Well article, but it doesn't go deep enough.
Before I make my main point, I should first state my vested interest. I have been an unsuccessful business person twice. The losses of my two businesses were used to reduce my taxes as wage earner. They have been a few years where I really didn't pay any tax either.
But my businesses were small. A $45,000 loss in the first business and about $100,000 in the second. If you have losses in a big business, here's how you can game the system:
You can afford to hire tax specialist lawyers. They will interpret the tax laws to your favor and threaten to take the IRS (USA) or Revenue Canada (Canada) to court. The tax men fear getting an unfavorable ruling in court. When that ruling is made, other wealthy people can use that case as precedent. So rather than getting laws more or less struck down by a precedent---and losing a whole bunch more tax revenue---the tax men often makes a deal with the wealthy person just before the case gets to the courthouse steps.
Small business people really can't use that technique. They just don't have enough cash to force litigation.
Let me explain this in another way. Honest accountants deem $10m should be paid in tax. The business person pays the tax lawyer $1m to find interpretations in the tax code--and the tax bill gets tossed into the legal system for a decade. The business person is still $9m ahead.
Methinks Mr. Trump did not make the deal with the tax man. Not surprising!