My suspicion is that Trump took dirty money from Russian interests to finance his real estate ventures, after he declared bankruptcy and the Great real-estate crash occurred (ca. 2009ff).
And here is the problem.
Out of over 500 companies that Trump managed, those companies have a combined total of 6 bankruptcies.
3 of them were for the same property, the Taj Mahal. The other 3 were for 2 other casinos in Atlantic City, and the Plaza Hotel in New York.
The Taj Mahal has an interesting history. First started in 1983, the original company was bought out when it was on the brink of bankruptcy in 1988, with the hotel still under construction. It finally opened in 1990, 3 years behind the original scheduled opening. In 1991 the Trump company did a Chapter 11 Bankruptcy to reorganize the debt. The loans on the property had been made by at least 4 different entities, this allowed them to be reconsolidated into a single financing package.
And the Taj was a huge financial drain from before it opened. Most of the debt of his hotel company is all because of that one hotel-casino. The "bankruptcy" of his Resort company was also a pre-planned Chapter 11. The company had already proposed to the bond holders to do a bonds-for-stock swap to cover the standing debt, and negotiations were still ongoing when the bonds became due in November 2004. The proposal was approved in December 2004, the Bankruptcy Court approved, and the bankruptcy was nullified.
The Bankruptcy of the Plaza was very similar. After buying the hotel, over $50 million was invested in repairs and renovations on the 80+ year old building. They were in active negotiations with Citibank to exchange debt for ownership in the building when the debt came due. So like the previous ones, they went into Chapter 11 Bankruptcy until the negotiations were completed.
A lot of people do not understand the difference between Chapter 11 and Chapter 7 Bankruptcy. Chapter 11 is simply a reorganization. And in each of the cases above, the negotiations into the resolution were already underway before it was declared. The Bankruptcy was simply a way to buy more time as the negotiations were completed.
Just because a company "goes bankrupt", that does not mean it is going out of business. That is Chapter 7, and that did not happen in any of the cases that a Trump owned company went "Bankrupt".
And the fact that his creditors in each case had no problem in accepting company stock in exchange for the debt shows they were not worried about making their money back. If they had no faith in the company itself, they would have refused the Chapter 11, and forced any of these into a Chapter 7 situation.