We tend to flag, or at least strongly resist speculation here, especially when one speculates as to facts that might support a theory. But, with respect to key aspects of Trump’s business status, and the potential conflicts with the Office of the President, we must speculate, because he simply won’t provide the facts to questions that must get asked.

So, I’m going to speculate, thus;

Trump is not only, “not a billionaire,” he carries so much debt that, relative to his hard assets, he’s poor, especially with respect to cash flow through cash intensive investments such as resorts, etc, where one has to pay large monthly bills to keep the lights on and the greens, well — green. In any given quarter, Trump faces situations where he doesn’t have the cash to keep up “appearances” and must borrow cash, at whatever rate, to maintain the cloak of worth, I mean wealth ...I mean, the wealth that makes up his self-worth.

I’m not a CPA. I’m a lawyer, but not one with any business experience. This is truly a layman’s “speculation” and experts here can tell me that I’m wildly wrong - which would be good. I look forward to learning. But, let’s start putting some real easy facts all in one place, ones we all agree don’t even need citation at this point.

1. We know that he promised to “self-fund” his campaign, and yet not only did he not “self-fund” it, he charged HUGE fees to his campaign to use Trump property. We also know that he never had anywhere near enough campaign money. From the beginning, the “Billionaire” had the “poorest” campaign.

2. He promised to donate all that money made in one evening to veterans groups, and had not done so when checked-in on, months later. (This is part of the larger pattern, a “Foundation” that he never paid money into, and hadn’t paid a lot of real money out of, one under criminal investigation. Most true billionaires have real foundations with real people who really help various causes because it helps business. It’s more polite to be worth billions if one can point to the appearance of “doing good” and yet Trump can’t even do that).

3. Upon winning the presidency, one of the first things he did was set up cash cow, meet/greets with his sons and various other tawdry behavior.

4. Even as President-Fucking-Elect he sells tickets to his New Years Eve party. Yet another potential conflict boil-up.

4. We know he took risks that could get a guy thrown in jail — paying off the Florida Attorney General $20,000 to drop the investigation into his Trump U and when he did it, he did so in yet another way that could get a guy thrown in jail — having his "charity" pay for it.

5. By the way, just what the fuck is a “billionaire international real estate developer” doing even setting up something as stupid as a “U” to begin with? Never mind “Trump Steaks" - Unless one simply needs easy cash?

My point is, at every single point where he could have simply made his life easier by “not charging” or “avoiding a conflict” or “staying out of jail,” he’s gone with the move that carried the most risk but picked up five figures, over and over. No, I don’t think it all can be blamed on being short-fingered.

Which leads to two relevant questions. Speculation. What if, the real reason that Trump can’t “divest” himself of his business interests is because “divestment” would leave bare that he still owes more money than he has? He’s insolvent.  What if he’s willing to put up with dancing the “Presidents can’t have conflicts” line because the alternative is “My debts outweigh my assets. I’m not rich, once one has stripped away the 757 and gold toilet, and I’m not willing to do that.”

Of course, I’m speculating, and I’m not a CPA or CFP. And, of course, you can simply read what people who are, actually, CPAs and valuation experts, people at Bloomberg, and see what they think (they still think he's rich, but note his debt doubled). But, Bloomberg basis its findings on something I’m not willing to trust — Trump’s reports, and specifically, they trust he’s accurately reported his debts. I find my lying eyes far more trustworthy. I scan the landscape and cannot escape one fact. Trump takes ruinous risks, monthly, to pick up $10K here or $20K there.

He has to. He’s poor.

And Putin knows it, and can prove it.

I’m speculating. Our President-Elect is free to “prove” me wrong.