Donald Trump Should Probably File for Bankruptcy, but Likely Won’t Because He’s Worried It Would Make Him Look Like a Loser: Report

As you’ve probably heard by now, Donald Trump is in an extremely large financial pickle, because he—a man who once uttered the words, “The beauty of me is that I’m very rich” and claimed to be worth nearly $9 billion—does not have enough cash to secure a bond for the $464 million he was ordered to pay the state of New York as he appeals the judgment against him. As a result, on Monday, New York attorney general Letitia James could start the process of seizing his assets. One way to avoid such a scenario would be for the ex-president and de facto GOP nominee to file for bankruptcy, giving him a monthslong, if not yearslong, reprieve from paying the judgement. However, according to The Washington Post, Trump doesn’t want to do that because he fears it would cause his supporters to question his financial success and whether or not he is the business genius he claims to be.

Yes, the Post reports that even though filing for bankruptcy appears to be one of Trump’s best options among a fast-dwindling set of alternatives, he “is not considering that approach, partially out of concern that it could damage his campaign to recapture the White House from President Biden in November,” according to four people familiar with the matter and close to the former president. “He’d rather have Letitia James show up with the sheriff at 40 Wall and make a huge stink about it than say he’s bankrupt,” one of the people said. “He thinks about what is going to play politically well for him. Bankruptcy doesn’t play well for him, but having her try to take his properties might.” While Trump may actually be right about that—it’s not hard to imagine him convincing his supporters that he’s the unjust victim of government tyranny, claiming America has devolved into a communist hellhole, and telling people they’ll be next—he is, of course, no stranger to bankruptcy protection. Between 1991 and 2009, Trump’s companies filed for Chapter 11 bankruptcy six times. (On the 2016 campaign trail, the Queens-born real estate developer insisted this was evidence of his brilliance.)

In a statement to the Post, a spokesman for Trump noted that the ex-president’s legal team had asked an appeals court for a stay of enforcement on the civil penalty (after an emergency appeals judge rejected the plea). “This is a motion to stay the unjust, unconstitutional, un-American judgment from New York judge Arthur Engoron in a political witch hunt brought by a corrupt attorney general. A bond of this size would be an abuse of the law, contradict bedrock principles of our republic, and fundamentally undermine the rule of law in New York,” said Steven Cheung. According to the Post, “Trump’s lawyers have expressed some optimism to him privately that appellate judges could decide to shrink the size of the bond he is required to post to avoid asset seizure.” What options are left if that doesn’t happen and the motion to stay is denied? “His next best bet is to find a liquid billionaire and do a quick buy-and-sell arrangement with him or her,” finance attorney and Republican National Committee member Richard Porter told the Post. “Then, if I’m advising that billionaire, I’m saying the upside is you can make some money and make friends with a guy who is likely to be president. The downside is you will be targeted if he loses.” Another potential downside is that a man famous for reneging on his debts won’t pay that billionaire back.

On Wednesday, The Wall Street Journal reported that Trump could soon receive an on-paper financial windfall of nearly $3.5 billion thanks to supporters driving up the value of Truth Social, which is set to go public as early as next week. But even if he does collect such an amount, it wouldn’t help his current predicament because he cannot sell his shares in the company for at least six months. “This is his worst nightmare from a personal and financial situation,” journalist Timothy O’Brien, who wrote a book about Trump in 2005 declaring that he was worth a fraction of what he claimed, told the Post, predicting the ex-president would start lashing out even more than usual.

Like clockwork, Trump took to Truth Social on Thursday to rage: “This Witch Hunt, between a bad Judge and a Corrupt & Racist Attorney General, is horrible for New York. Businesses are FLEEING, while Violent Crime flourishes. ELECTION INTERFERENCE!”

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