I have a feeling it works something like this:
I bought a building in 1980 valued at $1 million.
Reappraisal in 2000 after renovations valued it at $151 million
Revaluing in 2020, with 20 years of written off depreciation, has the building value as $100 million
Conclusion: TRUMP IS $50 MILLION IN DEBT
They seemed like legitimate debts. Some seem left over from developing the property itself, some of them are loans taken out with the buildings as collateral. Some of the debt is mortgages; the Doral golf course has 2 mortgages taken out on it. Trump hasn't paid principle on some of them in years, he may just be cycling them into new debt as they come due.
The value of the properties has
taken a major dive, especially since Wu Flu, and double especially for the assets in the New York real estate market, which has crashed hard. That doesn't affect the debt load, just the assets available to pay them off.
While Trump will get a pension, his post-Presidency prospects are up in the air as far as what he can or can't do.
Trump basically burnt his bridges and then some within Hollywood and the media running for President, so a return to the Apprentice is out of the question. Or getting cameos on TV shows and movies. He's also going to be living under the constant threat of retaliation prosecution (the NY State Prosecutors have outright stated they intend to go after him out of spite and malice once he leaves the White House and I don't even thing Biden/Harris saying "don't you dare!" as far as agreeing to squash all retaliation prosecutions against Trump in exchange for getting Trump to leave quietly will stop those fucks and their TDS. Especially since these are people who are still pissy that Obama gave Bush II and his crew a pass/banned retaliation prosecutions against them.
Trump MIGHT use his fortune/resources to finally start his own TV network or alternatively, join Fox News or OAN. The later is more likely, since OAN would probably pay Trump a lot more money than Fox News might be willing to spend, let alone Fox New not wanting to risk Biden and the DNC retaliating to them hiring Trump by doing what they've been wanting to do since Bush got elected: use the power of the federal government to purge Fox News from the airwaves by any means necessary.
Trump has clearly been losing tons of money since he became President. In fact, I'd go so far as to say if he's in financial trouble now, it's largely because of being forced away from business for 4 years. His empire seemed to require constant new developments to keep rolling.
I went through his current positions in a
follow-up post. If you gave me that starting position, and I didn't worry about my current living standard or keeping up appearances, I could easily survive the next 5 years of $450 million of debt coming due, without selling a large number of assets. You'd just need to keep operating income steady, bank it all, and use some bridge loans or lines of credit to smooth out the timing of the cash flows.
That may actually be Trump's post-Presidency retirement plan: live in an already-owned property, use the federal pension for living expenses, use the Secret Service budget for travel, and let his holdings coast through the debt payoffs while his kids stabilize the business empire.
As far as growing his wealth, though, I think you're right, he's done there. In fact, picking up a 2nd term may screw him over, if it prevents him and his kids from stabilizing the empire's finances for another 4 years. I don't think he gets out of it all without selling some of the underwater properties.
And I don't see him having the spare cash to start up a news network. Maybe a % stake in one, in exchange for constant on-air gigs. But his cash flow is going to be tight until he's approaching his 80s.