Forget about Super Tuesday, for Trump it’s going to be March Madness in court

In March, the first of four criminal trials Trump faces is set to begin. He also must resolve the looming question of securing the more than half a billion dollars in bonds he needs in order to appeal two crushing civil cases he lost earlier this year.

Trump’s legal travails have done little so far in denting his chances at being nominated for a third straight time to run as the Republican candidate for president — he has so far sailed through all the early primaries and is expected to cruise through the 16 primary states that vote on Tuesday.

But his battles in court this month are likely to be much more contentious and could put him a precarious position, at least financially. Instead of focusing on the campaign trail, Trump has spent increasing amounts of time huddled with lawyers. He has also been reallocating an inordinate share of campaign donations to pay for his legal defense.

Even after, on Monday, securing a notable win when the Supreme Court unanimously decided Colorado (and Maine and Illinois) could not unilaterally rule Trump ineligible for state ballot, it will be March Madness in the courts for the former president as he attempt to deal with all the issues stemming from his litany of legal challenges.

The bills are coming due

Perhaps Trump’s most pressing legal problem is actually a financial one. By the end of March, the real-estate tycoon and former reality-TV host must figure out how to post two enormous bonds worth over a half-billion dollars in order to pursue appeals in two civil cases lost in recent months.

In mid-February, Trump and his eldest sons were found liable in Manhattan for lying about the value of the family’s real-estate assets for years in order to get favorable rates from lenders in a case brought by New York Attorney General Letitia James. The trial judge in the case ordered Trump to pay $454 million in penalties and barred him from having any involvement in the company for three years, placing the business under the guidance of a court-appointed monitor. The Trump Organization was also blocked from borrowing money from any financial institution registered in New York state. 

Trump has claimed that the case and the verdict are politically motivated. 

That verdict came on the tail of Trump’s loss in a defamation case brought by writer E. Jean Carroll, who had accused the former president of raping her in a high-end Manhattan department store’s dressing room in the 1990s. In that case, Trump was ordered to pay Carroll, a former magazine columnist, $83.3 million in damages. Trump denied raping Carroll and says the defamation case and verdict, too, are politically motivated. 

Both cases require Trump to post all the money — either in cash or in the form of a bond — in order to proceed with his appeals. That has proved to be a gargantuan task. On Wednesday, Trump asked the appellate court to allow him to post just $100 million in the corporate fraud case as securing a bond for the full $454 million was proving impossible. His lawyers said he might have to sell some property, which he wouldn’t be able to get back even if his appeal were to be successful.

An appellate judge rejected the motion but did grant an interim stay on the bars against Trump and his sons running the company and getting loans from New York–registered financial institutions, which should provide him some leeway. A five-judge appeals panel has agreed to review the matter later this month. In the meantime, Trump has until March 25 to post the bond or the attorney general’s office could begin seizing his property. 

Stormy Daniels

While Trump seeks to resolve his financial quandaries, he also must prepare for the first criminal case to be brought to trial against him. That case, brought by Manhattan District Attorney Alvin Bragg, alleges that Trump falsified business records in attempting to obscure hush-money payments to adult-film star Stormy Daniels and onetime Playboy bunny Karen McDougal to bury their claims of having had affairs with him.

A trial date has been set for March 25.

The case revolves around an alleged arrangement Trump and his then-lawyer Michael Cohen had with the National Enquirer to identify potentially damaging stories about Trump as he was running for president the first time in 2015–16, and make them go away. The dark-arts tabloid practice is known as catch-and-kill.

Court documents laid out three instances in which Trump, Cohen and the Enquirer’s publisher, David Pecker, arranged for payouts to people shopping damaging stories about Trump, including Daniels, who was paid $130,000, and McDougal, who received $150,000.

The case primarily focuses on the payment to Daniels, which was made directly by Cohen through a shell company he had created. Trump is accused of falsifying business records by directing Cohen to be reimbursed through phony invoices for “legal services.” 

Trump has also dismissed the case as being politically motivated.

Bragg has emphasized that it is more accurately characterized as a case about election interference — seeking to get damaging personal information from becoming part of the public discourse ahead of a national election — than about hush money per se.

Some breathing room

Trump received a bit of breathing room on Wednesday in a case alleging he attempted to illegally overturn the 2020 election when the Supreme Court agreed to hear oral arguments over his claim to blanket immunity for his actions while president.

The case, brought in Washington, D.C., by special counsel Jack Smith, was initially slated to go to trial at the end of March but has now been pushed back as Trump has pursued his appeal in a bid to have the charges dismissed.

The Supreme Court scheduled oral arguments for April 22 and is expected to rule before the end of its session in June. Barring any other holdups, that would put the earliest  possible start date for the trial in September or October, with the general election coming Nov. 5.

More storm clouds

These pressing legal matters aren’t the only ones Trump faces. More distantly, he will have to defend himself against charges in Florida federal court accusing him of illegally keeping classified documents after he left the White House and refusing to return them when asked and, allegedly, willfully obstructing efforts by the federal government to achieve them. He also must deal with charges in a racketeering case in Georgia that accuses him and many of his advisers — several of whom have admitted guilt — of attempting to illegally subvert the 2020 presidential election there. 

From the archives (December 2023): Apology letters by Sidney Powell and Kenneth Chesebro in Georgia election case are one sentence long

Also see (February 2023): Fulton County, Ga., grand jury suspected some witnesses in Trump election case lied under oath, newly released report indicates

A preliminary trial date in the Florida documents case has been set for May 20, although the judge in that case, a late-term Trump appointee, has signaled that will be pushed back. Prosecutors in Georgia have sought an Aug. 5 trial date in the election case, but the judge has not yet set the calendar. That case has been plunged, at least temporarily, into disarray as the defendants have sought to have Fulton County District Attorney Fani Willis dismissed, alleging that her personal relationship with a special prosecutor she hired to handle the case created a conflict.  

The latest:

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Trump wins North Dakota Republican caucuses ahead of Super Tuesday contests

Trump Organization finance chief Weisselberg admits to perjury in civil fraud case