The article says "What the tax records for Mr. Trump’s businesses show, however, is that he has lost chunks of his fortune even before depreciation is figured in. The three European golf courses, the Washington hotel, Doral and Trump Corporation reported losing a total of $150.3 million from 2010 through 2018, without including depreciation as an expense."
So this is negative cashflow, not counting depreciation.
Reading the detailed breakdown, the only things he's done or invested in that have not lost money are two early properties he was forced out of but left a small stake in, and his reality TV appearances. Everything else has lost money.
To add to this: Trump International Hotel (the one in DC) was put on the market in Oct. 2019 for $500M. There were no buyers before the sale offering was canceled due to coivd-19.
You don't put a marquee property on the market if it is making money. Especially the one in DC. Especially while you are the current US president.
So this is negative cashflow, not counting depreciation.