Donald Trump lashes out as clock runs down on his $464m bond payment

The clock is ticking.

On Monday, Donald Trump will face a reckoning with the legal system as he never has before.

Alongside his four criminal cases - totalling 88 charges - the civil fraud case against the former president, his adult sons Don Jr and Eric, the Trump Organization and two of its executives, seems somewhat underplayed.

It does, however, go someway to undoing two of the greatest myths about Mr Trump which helped propel him into the public eye as a real estate mogul, reality TV star, and finally US president: that he is immensely wealthy and a great businessman, skilled in the art of the deal.

These myths were very publicly deflated after he was found liable for fraud in the case brought against him by New York Attorney General Letitia James.

In February, Justice Arthur Engoron ruled that Mr Trump must pay in excess of $464m for grossly inflating his net worth and the value of his assets for more than a decade to obtain favourable conditions on loans.

Mr Trump wants to appeal the ruling but needs to post bond to do so. Therein lies the problem — he doesn’t appear to have the cash, and 30 surety companies were “unwilling” to use his namesake properties as collateral.

The companies said they “will only accept cash or cash equivalents,” such as marketable securities, and typically would “require collateral of approximately 120 per cent of the amount of the judgment”.

That total is nearly $560m - which Mr Trump’s attorneys said in a court filing that he couldn’t come up with. However, Mr Trump has claimed on his social media platform, Truth Social, that he has $500m in cash acquired through “hard work, talent, and luck”.

In reality, he likely is relying on political action committees and the Republican National Committee to pay his mounting legal bills while he campaigns.

Ms James has said that her office is prepared to seize the former president’s assets if necessary to settle the judgment against him. State attorneys have filed the Manhattan court judgment in Westchester, the suburban New York county that is home to Trump National Golf Club and his Seven Springs estate, signalling a first move to do so.

Perhaps understandably, this massive hit to his wealth and image appears to have been getting to the 2024 Republican presidential candidate, currently in the midst of his campaign to return to the White House.

On Sunday, “Don Poorleone” was trending on social media platform X.

In typical fashion, Mr Trump spent the weekend posting about his situation on Truth Social.

He has previously lashed out at the judge, the attorney general, the basic foundations of the case, the clerk of the court (earning him a gag order), and the state and city of New York itself.

Just this weekend, he posted: “​​Leticia [sic] James has a TERRIBLE RECORD ON VIOLENT CRIME AS NEW YORK STATE ATTORNEY GENERAL. BUT AT LEAST SHE GOES AFTER TRUMP FOR DOING ABSOLUTELY NOTHING WRONG!

Shortly after that, he wrote that Judge Engoron had “fraudulently undervalued Mar-a-Lago” to create a “fake narrative”, calling him “grosssly incompetent and corrupt!!!”

He has also accused the Biden administration of orchestrating the case, saying that the “Trump hating attorney general ... takes her orders directly from the White House” adding to his familiar false charge of “election interference at a level never seen before!!!”

Mr Trump dubbed the prospect of the state seizing his property as akin to “communism” and claimed that businesses are either fleeing New York or have terminated plans to relocate there because of his case.

So, what happens next?

As the clock runs down, Mr Trump’s legal team are still trying to pause enforcement of the financial portion of the judgment and has requested oral arguments to make their case. It is likely that Mr Trump is also still trying to source the funds, from either a company or wealthy donor.

Speaking on CNN on Sunday, New York Representative Alexandria Ocasio-Cortez raised the spectre of what the former president might do to obtain money to cover the debt.

“I actually think that there is risk in not seizing these assets and the open window that exists in him trying to secure these funds through other means,” she said.

“We’ve seen a lot of interesting transactions happening with Truth Social and other means. And there’s a very real risk of political corruption.”

In an interview on Fox News, Mr Trump’s lawyer Alina Habba sidestepped answering whether Mr Trump may ask wealthy overseas donors in Russia or Saudi Arabia for help. The lawyer said that “she could not discuss strategy” instead of ruling out the prospect.

Mr Trump has resorted to asking supporters of his presidential campaign to put their hands in their pockets to bail him out and stop the state from seizing his properties.

“Hands off Trump Tower!” read the subject line of one fundraising email.

If Mr Trump does not come up with the money by tomorrow, and Ms James begins to target his assets, she will need a court order to do so. She has said that if Mr Trump doesn’t have the funds “then we will seek judgment enforcement mechanisms in court and we will ask the judge to seize his assets”.

The attorney general has previously said that she looks at Mr Trump’s 40 Wall Street property every day from her office indicating that it could be among the assets targeted. However, there are huge outstanding loans on the building which may indicate that it is low on the list. The same is true of Trump Tower.

Mar-a-Lago is also likely off the table as it is the former president’s legal residence and Florida has a homestead law that prohibits such seizures.

What’s more, the process of seizing property is long and complicated, so locksmiths won’t be at work on any Trump buildings this week.

On the other hand, Ms James could freeze personal and business bank accounts, which would provide direct access to cash to start paying down his debt, which is preferable to having to sell an asset.

It is worth remembering that the attorney general can seize other assets too, from jewellery and artwork to cars and even the former president’s prized plane, Trump Force One.

Ms Ocasio-Cortez commented to CNN: “I think Attorney General James has been handling this case with tremendous skill. It’s ultimately up to her determination, but it is my belief that all people should be treated equally under the law. And if that seizure of assets would be pursued to any other American, then Donald Trump should be treated the same.”

One potential lifeline — though some way off — is the possible merger of Truth Social and publicly-traded shell company Digital World Acquisition Corporation. Mr Trump’s 60 per cent stake is potentially worth billions of dollars but major shareholders of Trump Media cannot sell their shares for six months.

That stipulation – commonly used to prevent newly-public entities from signalling internal collapse or lack of faith in the company’s future – would also applu to the former president.

It is therefore looking like a pretty bleak Monday for the former president. Even as the deadline for his multimillion-dollar payout comes due, he is expected to be sitting in court for a hearing in a different trial — relating to his criminal prosecution over a hush-money payment to cover up the Stormy Daniels sex scandal.