The Monetary Minefield Awaiting an Ex-President Trump

And while Mr Trump has a large and dedicated following among the working class, for the most part they are not the future clientele of the resorts that have become magnets for suitors who want to rub their shoulders from a seated president or win favors.

Even if he lost, Mr Trump has raised more than $ 250 million in political donations since the election. While some of that money could be spent in a way that artfully or aggressively blends political work expenses with personal and business expenses, campaign funding laws would not allow Mr. Trump to use all of that to support his business.

Following previous challenges, Mr. Trump presented himself as a comeback kid, someone who independently rose above financial hardship by closing fabulous new deals. What he was hiding from view was the extent to which his father’s fortune and a second fortune in entertainment money – the current equivalent of nearly $ 1 billion – provided a reservoir of cash that could cover repeated failures.

In the late 1980s, when his Hodgepodge empire of casinos, hotels, an airline, and a soccer team collapsed under the weight of excessive debt and high costs, Trump’s father secretly stepped in and covered an interest payment of $ 3 million from a $ 15 million loss for a new home there.

Later, after the financial crisis that began in 2008, Mr. Trump defaulted on large loans on his Chicago Tower, much of his commercial space went vacant, and his casinos neared yet another bankruptcy. Although disaster loomed for the companies he led, Mr. Trump raised more than $ 154 million on The Apprentice from 2008 to 2011 and licensed his name for use on projects carried out by others.

About two years ago he received the last million dollar share of his inheritance. And the source of entertainment by the time he got into politics had nearly dried up, falling from winnings of more than $ 50 million in peak years to under $ 3 million in 2018. (Of course, defaulting his debts played into both of them, too Cases play a significant role in turnarounds.)

The Times received tax return data for Mr. Trump spanning more than two decades, including information from his personal returns through 2017 and his business returns through 2018. The records show that many of his companies have rarely, if ever, been told about their own.

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