Donald Trump’s tumultuous life has been rocked by bankruptcies, personal scandals, impeachments and election wins and losses, but nothing quite compares to the personal and financial crisis facing the once-and-possibly future president this week.

Trump is struggling to post a bond worth around half a billion dollars on Monday to stop the state of New York from targeting his assets following a huge fraud judgment. The situation he finds himself in threatens the empire that conjured the tycoon’s aura and assumptions of massive wealth that are critical to his self-identity and political brand.

But exemplifying the roller-coaster nature of his public career, Trump is also soon poised for a massive financial windfall. A deal to take his media company public promises to add about $3 billion to his net wealth – even if it won’t ease his cash crunch in the short term.

That’s not all. Trump may find out Monday when he will become the first ex-president to go on trial, as the judge hearing a Manhattan hush money case holds a critical hearing. The case, related to payment to an adult film star ahead of the 2016 election, could lead to Trump being a convicted felon by November’s election.

All of this is unfolding as he battles on multiple fronts to delay and discredit three other criminal trials, all in which he’s pleaded not guilty. He nonetheless has cemented his dominance over the Republican Party and leads President Joe Biden in some swing-state polls as he attempts the most stunning comeback in political history after he left office in disgrace after trying to steal the 2020 election.

It’s an extraordinary collision between Trump’s personal, legal and political controversies, all of which reflect the contradictions of a unique figure who has repeatedly flirted with financial ruin and tested the law but who has an uncanny capacity to dodge, or at least delay, accountability.

Since Trump swept aside all opposition in his triumphant sprint to his third-straight Republican nomination and has a strong chance of being the 47th president, his fortunes and fate are yet again inextricably entangled with the nation’s in a turbulent political era.

The ex-president’s most immediate threat lies in the need to post bond worth $464 million, including interest, after he, his adult sons and the Trump Organization were found to have committed massive fraud by a judge after a civil trial. The payment is needed to allow Trump time to appeal and to head off a threat by New York Attorney General Letitia James to start going after his assets and property empire if he cannot pay up.

The saga has been a humiliating one for the ex-president since it raises questions about his claims to a huge fortune. Trump’s lawyers have asked the appeals court judges to reduce or delay the judgment for ill-gotten gains, but they are yet to rule. His legal team said last week the bond amount was a “practical impossibility” for Trump, whose wealth is tied up in skyscrapers and golf resorts. And more than 30 insurance firms declined to underwrite the bond.

Trump’s legal team has also said he shouldn’t be required to sell assets to meet the deadline since doing so would create a fire sale devastating to his business. Trump has already been forced to come up with a bond guaranteed by an insurance firm for more than $90 million as he appeals a defamation verdict delivered by a jury hearing a case against him by the writer E. Jean Carroll.

It’s possible that Trump could find a private donor or donors to help him post the payment at the eleventh hour. And it’s not inevitable that his failure to do so would prompt James to move immediately. She could begin her asset search, for instance, by subpoenaing Trump for full details of his financial situation. But the New York attorney general has already lodged court paperwork that suggests Trump’s Seven Springs estate and golf course in Westchester County, New York, outside Manhattan, could be among her first targets.

As with his other outstanding legal cases, the ex-president has substituted a political defense for a legal one, claiming that he is the victim of persecution designed to keep him out of power. (There’s no evidence the cases, which proceeded through proper legal channels, are connected or that there is interference by the Biden White House.) Over the weekend, Trump prepared the groundwork for a new political assault, sending out a stream of frenzied fundraising appeals – including one titled “Maniacs want to seize Trump Tower” – and claimed he was standing in the way of the government coming after his millions of grassroots supporters.

The consequences of an asset seizure could be devastating for Trump and distract from his general election campaign.

“If he can’t deliver the security, and the court doesn’t give him dispensation from having to deliver the security, then starting on Tuesday, New York Attorney General Letitia James can start trying to execute against his property, which would be broken down into three categories,” white-collar litigator Mitchell Epner said on CNN on Saturday. One category could cover cash and bank and securities accounts. A second would encompass personal property ranging from clothing to vehicles and planes. The third contains real estate.

“On that spectrum, the cash can get grabbed the most quickly; personal property will take a little bit longer. And the real estate takes the longest period of time, but that process will start on Tuesday. And once that starts, he really can’t do anything in order to stop it from happening,” Epner told Fredricka Whitfield.

The spectacle of a presumptive nominee enduring such an ordeal would be explosive and could have unpredictable political consequences. This may explain why there is no sign yet that James is targeting Trump Tower – one of the citadels of his empire – despite the ex-president’s claims over the weekend. While Trump has successfully used his four criminal indictments to solidify his support base among Republican primary voters, the country is entering unprecedented territory with a presumptive nominee facing severe financial duress as a result of a fraud judgement. The staggering array of legal threats bearing down on Trump would be oppressive for any defendant, let alone a potential president, and raises the possibility that he could further alienate the moderate Republican, independent and suburban voters who helped Biden oust him after a single term in 2020.

Trump and his supporters have argued that the verdict against him in the case is massively inflated and have accused James, a Democrat, of bias. But Judge Arthur Engoron found that the ex-president, his adult sons and the firm had for years inflated the value of their assets to get better treatment from insurance firms and banks in a way that threatened the integrity of the financial system.

On Sunday, Trump used Truth Social to lash out at the prosecutor and judge, once again conflating his legal defense with his campaign. “THESE ARE NOT THE PEOPLE THAT MADE AMERICA GREAT, THESE ARE THE PEOPLE THAT ARE DESTROYING AMERICA!” Trump wrote.

The White House has done its best not to comment on the case, to avoid giving Trump more political ammunition. But some leading Democrats argue he’s now finding out that the law does not favor the rich and famous. “It is my belief that all people should be treated equally under the law,” Rep. Alexandria Ocasio-Cortez said on CNN’s “State of the Union” on Sunday. The New York Democrat added: “And if that seizure of assets would be pursued to any other American, then Donald Trump should be treated the same.”

Despite his money woes in New York, Trump could get a massive boost as early as Tuesday when a merger closes between Trump Media and Technology Group and Digital World Acquisition Corp., a shell company.

The former president will not be able to turn around and use his new wealth on paper to finance his bond, however, since he’s restricted from selling his shares for six months – and if he does so eventually, the value of the securities could plummet. There are also long-term concerns about the prospects of the firm, which is minuscule compared with social media giants such as X or Facebook.

Still, the merger agreement calls for Trump to own roughly 79 million shares of the new public company – and potentially tens of millions more if certain goals are hit. At times last week, Digital World was trading at around $43, although it eventually fell back. But Trump’s stake could be in the region of $3 billion, at least initially.

Only Trump could face a potentially existential threat to his financial security and his firm while at the same time getting a potential $3 billion windfall.

Monday could have been far worse for Trump, as it was the original date set for the debut of the hush money trial. But Judge Juan Merchan delayed proceedings until at least the middle of next month after more than 100,000 documents were turned over by the US attorney for the Southern District of New York related to the prosecution of Michael Cohen, Trump’s former lawyer, who is a key witness in the case.

The former president’s attorneys are now calling for a delay of 90 days or even a dismissal of the 34 counts of falsifying business records. Merchan could indicate on Monday whether the delay he has already put in place is sufficient to allow the trial to move ahead.

Trump has portrayed the case in the same way as all the others – as an attempt to keep him out of the White House. The former president has also pleaded not guilty in three other criminal cases – two over his attempt to overturn the 2020 election and one concerning the classified documents found at his Mar-a-Lago resort after he left the White House.

Some legal analysts, meanwhile, argue the Manhattan trial is the least threatening criminal case to Trump since it is unlikely to lead to jail time, even if he is found guilty. And since the alleged criminality in question dates to before the 2016 election, there’s also an argument that its impact on a general election eight years later could be limited.

But America has never seen an ex-president go on trial for anything – let alone months from the date when he will ask voters for a second term.

The only certainty about Trump is that he never stops shattering precedent.

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