NEW YORK – Former US president Donald Trump is expected to spend the morning of March 25 in the courtroom of a New York judge who might soon preside over his criminal trial and, ultimately, throw him behind bars. And that is not even the legal predicament that worries Trump most that day.

The hearing for his Manhattan criminal prosecution – in which he is accused of covering up a sex scandal to pave his way to the presidency – comes as he races to fend off a financial crisis arising from a US$454 million (S$613 million) judgment in another case. New York Attorney-General Letitia James, who brought that civil fraud suit against the former president and his family business, might begin to collect as soon as March 25.

To avoid a mortal threat to the Trump Organisation, Trump must persuade another company to post a bond on his behalf, promising that it will cover the judgment if he loses a pending appeal and fails to pay. Yet, Trump’s lawyers said in court papers that securing the bond would be a “practical impossibility” because he would need to pledge about US$550 million in cash and liquid investments as collateral to the bond company – an admission that laid bare Trump’s cash crunch.

Unless Trump strikes an eleventh-hour deal, Ms James could freeze his bank accounts, and begin the long and complicated process of seizing some of his properties. And barring Trump’s lawyers achieving an improbable legal triumph, the judge in his criminal case could set a trial date for as soon as in April.

The twin threats – on the same day, in the same city – crystallise two of Trump’s greatest and longest-held fears: a criminal conviction and a public perception that he does not have as much cash as he claims.

For decades, Trump employed a broad array of tactics to keep those fears at bay, learning from his well-connected father and his own ruthless lawyer and fixer Roy Cohn. After fending off local and federal investigations, not to mention financial ruin, Trump came to believe that any problems could be solved by personal connections – and a whole lot of money.

“If Trump uses one thing to score the game, it has always been money,” said Mr Jack O’Donnell, a former casino executive who worked for Trump in the early 1990s and wrote a tell-all book about him. “If he has more money than someone, he is winning and the other person is losing. And if someone has more money than Trump, he has the fear that someone will say he is losing to that person.”

Trump has also described the shame of becoming a criminal defendant four times over. Even as his advisers used the indictments to great effect in fund raising and galvanising his Republican base, Trump has conceded that the charges pained him.

“Nobody wants to be indicted,” Trump told reporters aboard his airplane last June. “I don’t care that my poll numbers went up by a lot. I don’t want to be indicted. I’ve never been indicted. I went through my whole life, now I get indicted every two months.”

It was a massive shock for a man who, until then, had navigated a wary path around law enforcement scrutiny throughout his long public life.

He was investigated criminally over a land acquisition in the mid-1970s, yet escaped unscathed. A federal special counsel examined possible ties between the Trump 2016 campaign and Russia, as well as his effort to obstruct the investigation as president, and recommended no charges. He was twice impeached by a Democrat-led House, but twice the Senate did not convict him.

Before 2023, nothing stuck.

“He’s been so lucky, and nobody’s ever had worse adversaries than this guy,” said Mr Ty Cobb, a lawyer who worked in the Trump White House during the special counsel investigation and has become sharply critical of the former president.

Some of it was luck, but his public relations strategy paid off as well. Trump deployed a mix of bare-knuckle tactics – attacking prosecutors as “corrupt” and guilty of the same conduct of which he was suspected – and arm-twisting charm.

Among Trump’s prized relationships was with Mr Robert Morgenthau, the Manhattan district attorney for decades.

While Mr Morgenthau was in office, he would joke privately that his pet charity, the Police Athletic League, was the only one to which Trump routinely donated. And when Trump supported Mr Morgenthau politically, some Trump Organisation officials were told they needed to write cheques of their own to the district attorney’s campaign, according to two people familiar with what took place. (People who worked with Mr Morgenthau, who died in 2019, said there was nothing directly involving Trump that crossed their desks that would have required investigation.)

The district attorney’s office, now held by Mr Alvin Bragg, was the first to indict Trump in 2023 before other prosecutors followed suit. The former president privately reacted with disbelief that his hometown district attorney had dared to come after him.

In 2021, when the office was intensifying its investigation, Trump told an interviewer that “Bob Morgenthau would not have stood for this”.

Mr Bragg’s case concerns a personally embarrassing episode for Trump: a $130,000 hush-money payment to porn actress Stormy Daniels, meant to bury her story of a sexual encounter with Trump. His fixer at the time, Mr Michael Cohen, made the payment. Trump, who has denied the affair, is accused of falsifying business records on his reimbursement of Mr Cohen.

Trump’s lawyers, as they do in each of his legal entanglements, are seeking to delay the trial past Election Day. If Trump is re-elected, the cases against him would probably grind to a halt.

The New York judge presiding over the case, Mr Juan Merchan, recently delayed the trial for three weeks, until April 15, and the hearing on March 25 will determine whether he postpones it further.

Despite the best efforts of Trump’s lawyers to delay or scuttle the case, it is the indictment that his advisers are the least concerned. They argue it is the least politically damaging to the presumptive Republican nominee, despite the personally mortifying details.

However, the New York Attorney-General’s civil fraud case, which accuses Trump of wildly exaggerating his net worth, has struck a particularly sensitive nerve with the former president.

Trump measures his wealth in the billions, a sum that largely stems from the value of his properties. Although valuing real estate is more of an art than a science, the Attorney-General disputed some of Trump’s purported estimates as wildly exaggerated, concluding that he inflated his net worth by as much as US$2 billion.

And then there’s his cash. Trump argues that he is relatively liquid for a real estate developer, stating in a deposition in 2023 that he had more than US$400 million in cash.

Although The New York Times was unable to verify the precise number, records and interviews show he recently had more than US$350 million in cash as well as stocks and other investments he can sell in a hurry. While significant, it is not enough to secure the appeal bond.

Typically, when facing outsize financial troubles, Trump has refused to concede that anything is wrong, dating back to when his business nearly collapsed in the early 1990s. People who have known him for many years say he has become accustomed to believing he can give the appearance of waiting out problems until circumstances change, banking on some sort of rescue at the last minute.

In the 1990s, banks bailed him out, even though he had massively overextended himself with a costly development of the Taj Mahal casino in Atlantic City, New Jersey.

With Ms James poised to begin enforcing the US$454 million fraud judgment, Trump appeared to be hoping for similar twists of fate. He could, for example, try to secure a loan from a private equity firm or a hedge fund. He is also hoping an appeals court will pause the judgment.

And then there is the windfall he could reap from his social media company, whose shares start trading on the stock market as early as on March 25. His stake is currently valued at roughly US$3 billion, but it might come too late: He is prohibited from selling for six months. Although Trump could find ways around that restriction that enable him to use his stake to raise cash for the appeal bond, no such deal appears imminent.

A post on Trump’s Truth Social platform on March 22 captured his insecurities. He claimed (falsely) that he had almost US$500 million in cash, and also claimed (falsely) that he had been planning to use that money to fund his own campaign; in reality, he last spent money on his own candidacy in 2016, and the amount was still nowhere near what he had claimed he would spend.

But his post was honest about at least one thing: To him, the US$454 million judgment was a “shocking number”. NYTIMES