Donald J. Trump will spend Monday morning in the courtroom of a New York judge who is expected to soon preside over a criminal trial and potentially end up in prison. And that's not even the legal predicament that worried Trump the most that day.
A hearing before a Manhattan criminal prosecutor accused of covering up a sex scandal to pave the way for the presidency, but trying to avoid a financial crisis stemming from a $454 million verdict in a separate case It was carried out during the struggle. New York Attorney General Letitia James, who filed a civil fraud lawsuit against the former president and his family business, could begin collecting as early as Monday.
To avoid a deadly threat to the Trump Organization, Mr. Trump must persuade another company to post bail on his behalf, and if he loses a pending appeal and fails to pay, a judgment will be issued. You need to promise to compensate. But Trump's lawyers said in court documents that securing the bond would be “practically impossible” because the bond company would have to post about $550 million in cash and liquid investments as collateral. This exposed the former president's confession to the light of day. Financial difficulties.
Unless Mr. Trump reaches an agreement in the 11th hour, Mr. James could have his bank accounts frozen and begin a long and complicated process to seize some of his assets. And unless Trump's lawyers score an unlikely legal victory, the judge in Trump's criminal case could set a trial date as early as next month.
These two threats, on the same day and in the same town, embody two of Mr. Trump's biggest and longest-standing concerns. It's the conviction and the public perception that he doesn't have as much cash as he claims.
For decades, Mr. Trump has employed a wide range of tactics to keep these fears at bay, learning from his well-connected father and his own ruthless lawyer and fixer, Roy M. Cohn. After dodging local and federal investigations, not to mention financial ruin, Mr. Trump came to believe that any problem could be solved with personal connections and lots of money.
Jack O'Donnell, a former casino executive who worked for Trump in the early 1990s and wrote a tell-all about him, said, “If Trump uses anything to decide the game, it's always money.'' “It was,” he says. “If he has more money than someone else, he's winning and everyone else is losing. And if someone has more money than Trump, then he's winning and everyone else is losing. You have a fear that someone will tell you that you are losing to that person.”
Trump himself has spoken four times about the humiliation of being a criminal defendant. Although his advisers used the indictment to great effect to raise money and energize the Republican base, the former president admitted he was troubled by the charges.
“I don't want anyone to be indicted,” Trump told reporters on a plane in June. “I don't care that the poll numbers have gone up significantly. I don't want to be indicted. I've never been indicted. I've been through all my life and now every two months has been indicted.”
This was a huge shock for a man who had previously taken a cautious path throughout his long public life, avoiding the scrutiny of law enforcement.
He was investigated criminally over land acquisitions in the mid-1970s, but escaped unharmed. A special federal prosecutor investigated possible ties between the Trump campaign and Russia in 2016 and his efforts to obstruct the investigation as president, and recommended no charges. He was impeached twice by the Democratic-led House of Representatives, but never convicted by the Senate.
Nothing was stuck until 2023.
“He was really lucky,” said attorney Ty Cobb, who worked in Trump's White House during the special counsel's investigation and became a harsh critic of the former president. No,” he said.
He was lucky, but so was his public relations strategy. Trump has used a combination of bare-handed tactics of attacking prosecutors as “corrupt and guilty of the same acts he is accused of” and his arm-twisting charms. did.
Among Mr. Trump's valuable relationships was his decades-long relationship with Manhattan District Attorney Robert M. Morgenthau.
During his time in office, Mr. Morgenthau privately joked that the only charity Mr. Trump regularly donated to was his own charity, the Police Athletic League. Also, when Trump supported Morgenthau politically, some Trump Organization executives were told they needed to write their own checks to the district attorney's campaign, two people familiar with the matter said. I made it. (People who worked with Mr. Morgenthau, who died in 2019, said there was nothing directly related to Mr. Trump that warranted an investigation.)
The District Attorney's Office, now headed by Alvin L. Bragg, first indicted Trump last year before other prosecutors followed suit. The former president reacted in secret disbelief that his hometown's district attorney had dared to go after him.
In 2021, as authorities ramped up their investigation, Trump told an interviewer that “Bob Morgenthau would not have done this.”
Mr. Bragg's lawsuit concerns a personally embarrassing episode for Mr. Trump. A $130,000 hush-money payment to porn star Stormy Daniels was aimed at burying her story about her sexual encounters with Trump. His fixer at the time, Michael D. Cohen, made the payments. Trump denies having an affair, but is accused of falsifying business records related to repayments to Cohen.
Trump's lawyers are asking for the trial, as well as each of Trump's legal entanglements, to be postponed until after Election Day. If Trump is re-elected, the lawsuits against him are likely to largely cease.
The New York judge in charge of the case, Juan M. Marchan, recently postponed the trial for three weeks until April 15, but a hearing on Monday will decide whether to postpone it further.
Mr. Trump's advisers are least concerned about the indictment, despite the best efforts of Mr. Trump's lawyers to delay or halt the proceedings. They argue that despite the personally humiliating content, it is the least politically damaging for potential Republican candidates.
But the New York attorney general's civil fraud case, which accused Trump of vastly exaggerating his net worth, struck a particularly sensitive nerve with the former president.
Trump's wealth is measured in billions, largely derived from the value of his fortune. Valuing his real estate is more of an art than a science, but the attorney general disputes that some of his own estimates are grossly exaggerated, inflating his net worth by as much as $2 billion. concluded.
And then there's his cash. Trump has claimed to be relatively liquid for a real estate developer, saying in his deposition last year that he had more than $400 million in cash.
Although The New York Times could not confirm exact numbers, records and interviews show that he recently held more than $350 million in cash, as well as stocks and other investments that he could sell quickly. While important, it is not sufficient to secure an appeal bond.
The realization that he may not have that much wealth comes as Trump claims he once sued journalist Timothy O'Brien for limiting his net worth to less than $250 million. Very sensitive. Mr. Trump lost.
On the witness stand at the Attorney General's trial, he declared that his wealth had been rather undervalued and that Mr. James was the real fraudster.
Trump typically refuses to admit anything is wrong, even in the face of huge financial woes, dating back to the early 1990s, when his business nearly collapsed. People who have known him for years say he has a habit of appearing to wait out problems until the situation changes, then hoping for some sort of last-minute relief.
In the 1990s, the bank bailed him out even though he was overextending himself and spending millions on developing the Taj Mahal casino in Atlantic City, New Jersey.
Mr. James is poised to begin enforcing his $454 million fraud judgment, and Mr. Trump appears to be hoping for a similar twist of fate. For example, he could seek financing from private equity firms or hedge funds. He also hopes the appeals court will suspend the sentence.
There's also a windfall he could get from his social media company, whose shares begin trading on the stock market on Monday. His stock is now valued at about $3 billion, but it may be too late. He is prohibited from selling for six months. Mr. Trump could find a way to circumvent that restriction and use his own equity to finance the appeal bond, but such an agreement does not appear imminent.
A post on Friday's Truth social platform captured Trump's anxiety. He claimed (falsely) that he had nearly $500 million in cash and also (falsely) claimed that he intended to use the money to fund his campaign. In fact, the last time he spent money on his own candidacy was in 2016, but the amount was still far from what he claimed he would spend.
But his post was honest about at least one thing. That meant his $454 million judgment was a “shocking number” for him.