Trump legal threats set to coincide
Criminal case, civil suit both in play Monday
NEW YORK — Donald Trump is expected to spend his Monday morning in the courtroom of a New York judge who might soon preside over his criminal trial and, ultimately, throw him behind bars. And that’s not even the legal predicament that worries Trump most this day.
The hearing in 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 $454 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 Monday.
To avoid a mortal threat to the Trump Organization, 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 in court papers said that securing the bond would be a “practical impossibility,” because he would need to pledge about $550 million in cash and liquid investments as collateral to the bond company.
Unless Trump strikes an eleventh-hour deal, 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 next month.
The twin threats — on the same day, in the same city — crystallize two of Trump’s 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 lawyer and fixer, Roy Cohn. To do so, he used personal connections, and a whole lot of money.
“If Trump uses one thing to score the game, it has always been money,” said Jack O’Donnell, a former casino executive who worked for Trump in the early 1990s and wrote a tell-all book about him. “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 galvanizing his Republican base, Trump has conceded that the charges pained him.
“Nobody wants to be indicted,” Trump told reporters aboard his airplane in 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 major 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 and recommended no charges. Before 2023, nothing stuck. “He’s been so lucky, and nobody’s ever had worse adversaries than this guy,” said Ty Cobb, a lawyer who worked in the Trump White House during the special counsel investigation.
Some of it was luck, but his public relations strategy paid off as well. Trump deployed a mix of bare-knuckle tactics and arm-twisting charm.
Among Trump’s prized relationships was with Robert Morgenthau, the Manhattan district attorney for decades.
While 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 Morgenthau politically, some Trump Organization officials were told they needed to write checks of their own to the district attorney’s campaign, according to two people familiar with what took place. (People who worked with 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 Alvin Bragg, was the first to indict Trump last year before other prosecutors followed suit. The former president privately reacted with disbelief that his hometown district attorney had dared to come after him.
Bragg’s case concerns a personally embarrassing episode for Trump: a $130,000 nondisclosure agreement to a pornographic film actress named Stormy Daniels that was meant to bury her story of a sexual encounter with Trump.
Trump’s fixer at the time, Michael Cohen, made the payment. Trump, who has denied the affair, is accused of falsifying business records about his reimbursement of Cohen.
LEGAL WOES
Donald Trump must post bond in his civil fraud suit on the same day of a hearing in a nondisclosure agreement case.