A Make-or-Break Legal Week for Trump?

Donald Trump is staring down a fraud settlement that could bring him to financial ruin, a judicial opinion that could undermine his defense against criminal charges related to election interference and a Supreme Court case that could keep him off the ballot come November.

And there’s a good chance that all three legal dramas see major movement next week.

Judge Arthur Engoron, who is presiding over Trump’s civil fraud trial, allowed a self-imposed Jan. 31 deadline to slip, though a ruling is expected imminently that would finalize damages incurred when Trump committed fraud by inflating his net worth to obtain favorable treatment from banks and insurers. But with the delay, Engoron has pushed his ruling into the same week the high court considers Trump’s ballot status and anticipation heightens for what was promised to be an expedited ruling on presidential immunity that could upend Trump’s several criminal cases.

While the reason for Engoron’s delay is unknown, the stakes are high. New York Attorney General Letitia James is seeking a staggering $370 million penalty from Trump. The ruling will also determine whether Trump is barred from participating in New York’s real estate industry or running any company in the state – a potentially blistering decision that could effectively eviscerate the business empire he built over decades, which ultimately propelled the real estate mogul to the world’s most powerful political position.

The long-running civil fraud case has been a source of intense frustration for the likely Republican presidential nominee, who is certain to appeal Engoron’s decision.

Notably, the pending judgment comes in the wake of a jury ordering Trump to pay $83.3 million in damages for defaming writer E. Jean Caroll. Combined with the forthcoming damages assessed for fraud, the total could near half a billion dollars and call into question the ability of Trump to pay such sums – or worse for him, strain his finances 10 months ahead of the 2024 presidential election.

Trump is already siphoning a portion of his political donations to pay legal fees associated with the 91 criminal charges filed against him in four indictments. In 2023 alone, The New York Times reported, Trump spent roughly $50 million in donor money on legal bills and investigation-related expenses.

Meanwhile, the Supreme Court will hear oral arguments in Washington on Feb. 8 in a blockbuster case that could prevent Trump’s name from appearing on ballots come November.

In December, the Colorado Supreme Court found Trump ineligible to hold office under the 14th Amendment of the Constitution. Specifically, they sided with a lawsuit brought on behalf of a group of Republicans and independents who argued that Section 3 of the amendment prohibits an “officer of the United States” who took an oath to support the Constitution and then “engaged in insurrection” from holding office again.

Amicus briefs flooded the high court leading up to next’s week’s arguments, parsing every detail of the amendment, including, for example, whether the article in question is “self-executing” or needs an act of Congress to be enforced, or whether the attack on the Capitol amounts to an insurrection and whether Trump actively participated in it.

The decision – put before a 6-3 conservative majority of which Trump installed three justices himself – is set to have major implications for American democracy and is notably just one of at least three cases the justices are poised to hear that could impact the 2024 presidential election.

But in addition to the New York civil fraud judgment and the high court arguments on the “insurrection clause,” Trump is also awaiting a decision from the U.S. Court of Appeals for the D.C. Circuit, where a panel of three judges is poised to issue a decision about whether the former president and his defense team can claim presidential immunity as a defense against criminal charges that accuse him of inciting a violent insurrection at the Capitol and attempting to overturn the results of the 2020 presidential election.

At a hearing last month, where Trump’s attorney and Justice Department prosecutors squared off over the issue, the panel of three judges seemed deeply skeptical over Trump’s reliance on immunity.

Among other things, the judges took issue with the underlying assumption from Trump’s lawyer that the Senate must convict a president first through impeachment in order for prosecutors to be able to file criminal charges against him. They pointed out that many Senate Republicans, including Minority Leader Mitch McConnell, voted against impeaching Trump based on the assumption any criminal activity would be handled by the criminal justice system. They also questioned the limits of presidential immunity – at one point asking Trump’s lawyer whether the same logic would apply, for example, to a president who used the military to assassinate a political rival.

While many legal experts ventured that the judges might deliver a decision within days of the hearing, given that they seemed in lock-step with one another. Their silence thus far benefits Trump, whose legal strategy for the 91 criminal charges lodged against him in four indictments is rooted in delaying proceedings. And while most continue to assume the judges will ultimately reject Trump’s immunity claim, the former president is certain to appeal such a ruling to the Supreme Court.