“Whoever Owns Trump’s Enormous Debts Could Be Running the Country” - Washington Monthly:

Many rich tax cheats will tell the IRS they are broke while hiding their true wealth elsewhere.  But Donald Trump isn’t just a tax cheat pretending to be broke for the feds. He appears to actually be broke. He inherited money from his father, squandered it on failed casino investments, offloaded the losses onto creditors, and then remade himself as a personal brand machine selling the rights to his name. He played a fake billionaire on TV and made significant money from doing that. Remarkably, adopting a fake reality TV show persona for public entertainment value may be the closest thing to honest work Trump has ever done.  But rather than being content to invest those proceeds wisely, he went on another foolish real estate spending spree. His properties old and new are losing ridiculous amounts of money–he has lost a shocking $315 million dollars in the last 20 years at his golf courses alone.

One fact stands out far above all the others in its staggering implications: Donald Trump is personally responsible for $421 million worth of loans coming due in the next few years. Not his business. Him. Personally. He has no means of repaying them. He already refinanced his few profitable properties, and sold off most of his stocks to stay afloat. He appears short on liquidity. And we still don’t know to whom he owes the money.

I have generally been skeptical of the more grandiose Trump-is-a-puppet theories. However, this idea that he is on the hook to a bunch of different creditors—any of whom might come calling at any moment—seems much more credible to me.