Following Friday's decision in former Donald Trump's New York civil fraud trial, in which he was fined $354 million plus interest, the former president faces what could be $540 million in potential damages and fines resulting from his civil trials over the last year.
Late week, the judge overseeing E. Jean Carroll's defamation case against Trump ordered Trump to pay the former Elle magazine columnist $83.3 million in damages on top of the $5 million he owes her from an earlier sexual assault trial. This week, the judge overseeing Trump's civil fraud trial fined the president $354 plus interest of around $100 million for what the judge determined was a decade of fraudulent business deals.
The costly cases shine a renewed light on the former president's finances and could call into question Trump's liquidity, as he runs headlong into multiple criminal trials and an historic presidential election this year.
MORE: Trump civil fraud trial updatesWhile Trump's donors have largely footed the bill for his campaign expenses -- with Trump's political committee spending more than $50 million on his campaign in 2023 -- the legal cases present a stickier challenge for Trump, who has built a reputation around his wealth. Courts allow defendants multiple mechanisms to collect damages, including liens and wage garnishments, and the fines are not dischargeable through traditional protections like bankruptcy.
Multiple legal experts who ABC News spoke with suggested that Trump is unlikely to front the fines immediately, and will instead opt to delay any payment using a bond secured by his assets until after he exhausts his appeal options.
"You can post the full amount yourself or you can get a bond posted by a third party," according to former federal prosecutor Josh Naftalis. "You can kind of think of it as insurance, with a third party on the hook and you pay a portion."
Here's how Trump might deal with his civil obligations.
When a jury first awarded Carroll $5 million in damages last year, Trump opted to cover the bill by moving cash into an escrow account.
Last year when Trump was deposed in the civil fraud case, the former president claimed his company had more than $400 million in cash.
"We have, I believe, 400 plus, and going up very substantially every month," Trump said.
Trump's 2021 statement of financial condition -- the last year available from his trial -- represented that the former president had $293,800,000 in cash and cash equivalents. However, the New York attorney general alleges that the number was falsely inflated, including $93.1 million which Trump should not have listed as a cash equivalent.
The Trump Organization has scored multiple profitable deals since Trump left the White House, while also slowing their acquisitions. In 2021, Trump and Vornado Realty Trust -- the former president's partner in a San Francisco skyscraper -- received $617 million from a $1.2 billion bond sale. Trump owns a minority stake in the property, and it's unclear how much Trump directly netted from the deal.
In the following year, Trump sold his Washington, D.C., hotel for $139,408,146 which netted him a profit of $126,828,600 according to the attorney general. Last year's sale of a New York golf course also resulted in nearly $60 million in profit.
It's unclear how much of those profits Trump held onto as cash, rather than using the profits to service other debts or fund projects. Based on his 2023 personal financial disclosure, Trump paid off multiple loans and reduced his Deutsche Bank loan down to $45 million, while also taking out new loans from Axos Bank. Listing over 100 sources of income -- and doubling his number of business holdings since leaving the White House -- Trump reported having over a billion dollars in earnings.
But even with hundreds of millions in cash and equivalents, Trump is more likely to cover his legal obligations using what's called a "supersedeas bond," secured using some of his other assets, according to Stuart Levine, a Baltimore-based business attorney.
"He's in a rarefied world -- it's quite different from the one that you and I inhabit," Levine said.
If Trump opts to secure his bond using one of his properties as collateral, a bond company would likely want the asset to cover roughly 125% to 150% of total amount, according to Ryan Saba, a civil litigation and trial attorney.
"The problem is nobody knows what Trump's collateral is or what collateral he has," Saba said. "Think of a bond as like a mortgage -- a bank is not going to give you a mortgage unless the value of the property exceeds the mortgage."
In fact, if Trump ultimately loses his fraud case appeal or loses the right to do business in New York, he might consider rapidly liquidating his New York-based assets, Levine said.
Trump owns multiple properties in New York, including his eponymous Trump Tower on Fifth Avenue, an adjoining retail space called Niketown, Trump International Hotel and Tower, 40 Wall Street, a partial stake in 1290 Avenue of the Americas, two upstate golf courses, and an estate called Seven Springs.
Appraised in 2016 by Cushman and Wakefield at approximately $56.6 million, the 230-acre Seven Springs estate is used as a "retreat" for the Trump family, according to Trump International Realty. However, a unique and historical property like Seven Springs has a high upkeep and maintenance cost that eliminates many buyers, according to expert appraiser Ronald McInerney Jr.
"This type of estate does take a special type of person," McInerney Jr. said.
Trump also owns golf courses in New York's Hudson Valley and Westchester regions, but the sale of those properties is unlikely to make a serious dent in Trump's legal obligations. A review of golf course sales in New York over the last five years conducted by golf course appraiser Robert Gorman found that the average course sold for roughly $2.5 million.
With high overhead costs and low overall revenue, the courses often attract a limited array of buyers, according to Gorman.
MORE: Trump's $370M civil fraud trial is nearing an end. Here's what to knowTrump's 2021 financial statement valued his New York City properties as roughly $2.2 billion, but quickly selling those properties in a period when New York has a historically high commercial vacancy rate could be difficult, according to multiple appraisers who spoke with ABC News. Adding to the difficulty of selling the properties is Trump's mixed reputation in New York.
"It's really difficult when you're talking about properties like this, which are owned by a controversial president who is now involved in this major fraud case," said Michael Vargas of Vanderbilt Appraisal Company. "The regular measures of value I don't think really apply to properties that are involved with his ownership."
Even Trump's famous penthouse in Trump Tower -- which competes in size and location with other high-end residences -- might be a challenge to sell, according to expert appraiser Michael Maloney.
"It's a great size apartment, so it truly is a trophy property sitting on top of Trump Tower," Maloney said. "But he's got a lot of people -- 50 percent of America -- who don't like the man."
However unlikely, Trump could consider having some of his companies declare bankruptcy based on the decision, according to Cardozo Law School professor Pamela Foohey. Chapter 11 bankruptcy could allow some of the companies involved in the case to reorganize, could keep the businesses afloat, and would set a long-term plan to pay off debts.
Trump's businesses -- such as the Taj Mahal in Atlantic City and the Plaza Hotel in New York -- filed for Chapter 11 bankruptcy protection in the 1990s, which the former president defended as smart business moves.
"I've done it four times out of hundreds, and I'm glad I did it. I used the laws of the country to my benefit," Trump said in a 2015 debate.
But bankruptcy is unlikely to be an effective long-term solution for Trump, according to both Foohey and Illinois College of Law professor Robert Lawless. Filing bankruptcy to avoid legal fines and penalties might invite a lawsuit, and legal fines are generally not dischargeable through bankruptcy, according to Lawless.
And as Trump approaches the 2024 election, filing for bankruptcy could be a political liability.
"Donald Trump has made a big deal about how he never personally filed bankruptcy," Foohey said. If Trump does go down that path, said Foohey, "I don't think they will file until the election is over."