But now, the properties and businesses emblazoned with his name face an unprecedented threat, following a ruling against him in a civil fraud case last month.

On Monday, Trump faces a deadline to post his bond, after Judge Arthur Engoran ordered him to pay a total of $454m for inflating his wealth to fraudulently secure loans and business deals.

If he fails to meet the cut-off date, New York Attorney General Letitia James could start to seize Trump’s assets, including his estates and other properties.

Trump has portrayed the effort as yet another “political witch hunt” meant to derail his 2024 presidential ambitions. James’s office has, in turn, suggested Trump is attempting to evade a public assessment of his much-vaunted personal wealth — with critics long arguing he is only worth a fraction of what he claims.

Earlier this week, Trump’s lawyers even told a New York appellate court that it was “not possible” for the former president to pay the bond in time.

But on Friday, a possible lifeline emerged: Trump Media, which hosts the social media platform Truth Social, entered into a last-minute merger with a wealthy shell company, likely to increase Trump’s wealth.

It remains unclear whether the merger will be enough to head off the looming deadline. Here’s all you need to know about Trump’s present financial woes — and what his outlook is as he prepares to post bond.

What was the civil fraud case about?

Attorney General James had been investigating Trump, his children and key members of his businesses for years, on allegations they had inflated their wealth to fraudulently secure more advantageous deals.

That includes tweaking annual financial statements to increase the value of Trump’s properties and other assets. Those statements, in turn, were presented to banks and other firms he did business with.

James, for instance, pointed to discrepancies in the value of Trump’s sprawling Mar-a-Lago estate in Florida. Trump and his associates had claimed it was worth $739 million on financial statements, but James cited estimates that put its value far lower.

On February 16, Judge Engoran sided with James: He found that Trump, his company, and his sons Eric and Donald Trump Jr had attempted to defraud investors by lying about their wealth. Trump’s legal team has since filed an appeal.

What is a bond?

Basically, Judge Engoran decided in his ruling that Trump must pay back the money he gained from lying in his financial statements.

But Trump does not have to pay it right away. That is where the bond comes in.

The bond requires Trump to put up the money in advance, to ensure that he will pay even if he loses his appeal.

Why hasn’t Trump posted the bond?

In court filings on Monday, Trump’s lawyers said that it was “not possible” for Trump to post the bond, which would require them to gather collateral worth $557m.

They explained they had spent “countless hours” negotiating with insurance companies but were turned down by more than 30 companies. The companies willing to entertain such a massive underwriting would only accept cash collateral, and not assets like property.

James’s office, however, has cast doubt on Trump’s inability to find a company to back the bond. In court papers, James’s team suggested Trump may not be willing to put up his properties as collateral, to avoid revealing that “his holdings are not nearly as valuable” as he claims.

This is not the first time Trump has scrambled to fulfil a multimillion-dollar bond, though.

He previously struggled to find an underwriter for the $91.6m bond he needed earlier this month, as he appealed a ruling against him in a separate civil case.

In that instance, a judge had found Trump liable for defaming writer E Jean Carroll, who had accused the former president of raping her in the 1990s.

Insurance giant Chubb backed Trump’s bond in that case, but it has not stepped in this time around.

What if he does not pay?

Trump has a few options left.

He could attempt to convince an appeals court to intervene before the deadline, granting him an extension or lessening the bond. Or he could also seek cash from elsewhere: Trump’s legal team has fielded questions in recent days about whether he would appeal to foreign funders.

He could also try to quickly sell one or more properties to raise the money, but that is considered unlikely.

If he does not meet the deadline, James said her office is ready to begin seizing Trump’s assets.

“We are prepared to make sure that the judgement is paid to New Yorkers, and yes, I look at 40 Wall Street each and every day,” James told ABC News in February, referring to Trump’s 72-storey skyscraper in the heart of the New York’s Financial District.

Trump also has several other landmark properties across New York City, including his 58-storey Trump Tower condominium building on Fifth Avenue.

On Thursday, James’s office filed a judgement in Westchester, New York, where Trump’s Seven Springs golf course and estate are located.

The move is a first step in the legal manoeuvring that would be needed to seize any property in the area.

So does that mean Trump properties will be seized?

After Monday, James’s office may take actions to start seizing some of Trump’s assets.

But Nikos Passas, a professor of criminology at Northeastern University, told Al Jazeera, “It’s not going to be simple.”

Passas said not to expect any particularly flashy moves by the attorney general’s office if Trump fails to post his bond. Though many properties bear the Trump name, he explained “a lot of these assets do not have direct ownership and clear ownership”.

“You have all kinds of arrangements that are designed and structured in a way to protect the ultimate beneficiaries,” Passas said.

Even attempts to seize properties with direct links to Trump and the civil case will likely result in prolonged court proceedings, he added.

However, there are likely more short-term measures James can take to freeze or impose restrictions on how Trump uses his bank accounts.

Will Trump’s actual worth be revealed?

Passas also explained that James could subpoena for further information about Trump’s personal finances if he fails to make the bond payment.

That could finally reveal the true value of Trump’s assets, something that has been the subject of speculation — and alleged obfuscation — during his entire political career.

“If he does not comply, then we’re talking about contempt of court, which possibly includes additional sanctions all the way to jail time,” Passas said. “So this could all go in that direction.”

The merger of Trump Media and the shell company Digital World Acquisition Corporation on Friday offers a possible 11th-hour lifeline for Trump in the case, but it hardly guarantees he will be able to meet the looming bond deadline.

The current valuation of the deal boosts Trump’s net worth by $3bn, but that amount is currently on paper only and could change drastically when the company begins publicly trading, Passas explained.

Per the agreement, Trump will be unable to sell his shares for six months, meaning the merger will not immediately affect Trump’s cash on hand.

However, the inflation in theoretical wealth could be enough to convince a company to underwrite the $454m bond.

“His negotiating position has improved,” Passas said. “Whether that is enough for the companies remains to be seen.”