Like many on Wall Street, I’ve been left wondering how Donald Trump will be able to afford the more than $450 million penalty, including interest, that Judge Arthur Engoron imposed on him last week as a result of the civil fraud lawsuit brought by New York State Attorney General Letitia James as well as the $83.3 million he owes E. Jean Carroll after he lost two defamation cases she brought against him. Assuming that at some point he loses all his appeals, can he get the cash he needs to pay his debts? Is he liquid enough for the appeal bond in the meantime? Will he be able to find someone to post the bond and take the risk of his credit? And that ignores, for the moment, the increasing possibility that he might also have to pay the I.R.S. $100 million or so in back taxes, as a result of his improper deductions over the years. 

The challenge of forking over $530 million, or so, recalls for me the billions Trump’s various real estate and casino companies failed to repay to creditors back in the 1980s and 1990s, forcing some five or six of those companies to file for bankruptcy protection. As Trump is the first to point out, he himself has never filed for bankruptcy, even if the various corporate entities he once controlled have. Will the current round of legal setbacks force Trump into personal bankruptcy for the first time, as the high-octane investigative reporter and Pulitzer-prize winner David Cay Johnston has suggested?