Analyst: Trump wanted to buy time in his trial and he did it 3:45

(CNN) --

 Donald Trump faces a liquidity crisis as deadlines to settle the more than $500 million he owes in judgments quickly approach.

On Wednesday, a New York appeals court judge refused to give the former president additional time to satisfy a $454 million judgment in a civil fraud case.

A federal judge is about to decide whether he grants Trump's latest legal effort to delay or release a fraction of an $83.3 million judgment he owes E. Jean Carroll in a defamation case.

Last week's fight reveals the challenges Trump faces in raising the combined sentences by a total of $537 million.

In asking for relief, Trump's lawyers told the judges that posting the bonds could cost him an additional $104 million — their estimate of the fees he would have to pay.

Trump's lawyers said he may have to divest some of his property in “urgent circumstances” to raise cash quickly, tap the capital markets or find another source of cash.

Last month, Trump began selling $399 gold sneakers.

The sneakers that Trump started selling (Credit: Chip Somodevilla/Getty Images)

“It is a really substantial problem.

He really is between a rock and a hard place,” said Adam Kaufmann, a criminal defense attorney.

The liquidity crisis challenges Trump's long-projected image of a successful businessman with deep pockets and a maverick's ability to overcome legal and financial problems.

He leveraged that reputation to reach the White House in 2016.

Now, the leading Republican presidential contender in 2024 could end up deep in debt to a bank, a donor or some other source of capital.

Adding to the uncertainty about Trump's future earnings are the four criminal charges he faces.

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On Thursday, Carroll's lawyers pointed to Trump's growing legal problems in urging the judge to reject Trump's request to delay or reduce the bail amount in his case.

“If Trump is convicted of even a subset of the 91 felony charges brought against him, the implications for his ability to satisfy the sentence here could be significant.

And even before a conviction, Trump's 'brand' (supposedly his most valuable asset, although not one that can easily be used to satisfy a civil judgment) may suffer as a result of the various legal proceedings in which he is embroiled," they said. Carroll's lawyers.

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Trump's reputation for not paying lawyers and others could hurt his ability to raise cash.

Trump can post the cash himself or obtain an appeal bond, which is often backed by cash or easily marketable securities, but the size of the sentences complicates the process, lawyers say.

It's unclear how much cash Trump has on hand.

Last year he testified under oath that he had more than $400 million in cash.

According to the New York attorney general's office, in 2021 Trump's 30% stake in a partnership with Vornado, a real estate investment company, was worth about $200 million, but Trump would need to sell that stake to convert it into cash.

Trump is unlikely to exhaust his entire cash position, as the properties have invoices and payrolls.

Trump offered to post $100 million bail to cover the New York attorney general's case, but the appeals court judge rejected it.

The deadline for sentencing in the Carroll case is in less than two weeks unless that judge grants Trump's request to delay or reduce the payment.

He has until the last week of the month to serve his sentence for civil fraud or face the possibility of the state taking action to seize property.

The magnitude of the sentences raises practical questions about how Trump could get his hands on the cash.

On Wednesday, the appeals court judge lifted a condition at Trump's behest: a ban that prevented him from obtaining loans from regulated financial institutions in New York.

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Big lenders

Many of the world's largest banks stopped lending to Trump decades ago.

Deutsche Bank, which he repeatedly tapped to finance real estate deals, ended its relationship with Trump after January 6, 2021. Signature Bank, another former Trump lender, also stopped doing business with him after the attack on the U.S. Capitol Joined.

Trump turned to Axos Bank, a California lender, in 2022 for a $100 million loan to refinance Trump Tower, but it is unclear whether that bank would lend money to Trump again.

CNN's calls to the bank and its CEO, Greg Garrabrants, were not returned.

Lawyers say Trump could try to take equity out of certain properties, but if there are outstanding mortgages or existing loans that could make it more difficult because a bank wouldn't want to be second in line to collect the money.

Another potential complication: The Trump Organization stopped preparing a personal financial statement for Trump two years ago, so a lender would have to be comfortable with the financials and could request an appraisal of the properties, which also takes time.

Clearance sale

Trump's lawyers said that without postponing sentencing, Trump may have to sell some of his properties in what could amount to a liquidation sale.

"If you were to sell a property, it would be a pretty tough market, but even if it wasn't, potential buyers would smell blood in the water and push for pretty strict terms," ​​Kaufmann said.

Trump has owned most of his properties for years, so if he is forced to sell them, he could incur a large tax bill unless he can offset it with losses.

"There are practical issues" in selling property, said Jeremy Saland, a criminal defense attorney.

“That's a nightmare.

How many properties will you have to offer to achieve that?”

Any sale would have to be reviewed by the Trump Organization's court-appointed monitor, retired Judge Barbara Jones, who will remain in office for three years.

Transfers over US$5 million must also be reported to Jones.

Process to obtain bail

Another possible scenario is to get a bond.

Appeal bonds represent just one percent of the surety business, according to the Surety & Fidelity Association of America.

As rare as appeal bonds are, the need for an individual to obtain such a massive bond is significantly less common.

"It's harder for an individual than it is for a company to get a very large bond," said David Shick, co-founder and president of ProSure Group, a bond surety broker.

Underwriters typically want cash or easy-to-sell assets to back the bond, but if they were to accept property, it could be more expensive.

For example, the bond issuer might want, say, $200 million in assets as collateral for a $100 million bond to cover the time and effort required to sell the property, if the client loses an appeal, he said. he.

Shick said that for large judgments it is possible for several insurance companies to band together.

"It's unusual, but so is the size of the bail," he said, adding that "the court will determine what they will accept and what they will not accept."

In any situation where a company decides to back a large bond, especially if the collateral is illiquid like property, Shick said, "it all comes down to a business decision about who you do business with."

E Jean CarrollInvestigations against Donald Trump