With Monday fast approaching, it seems unlikely that the former president will be able to meet this deadline unless an appeals court intervenes or he can post a bond for the full amount.

Last month, New York Attorney General Letitia James secured the judgment against Trump and his co-defendants after a months-long trial. Judge Arthur Engoron determined that they had committed "persistent" fraud over a span of years, resulting in a judgment of over $350 million. With pre-judgment interest, the amount has now inflated to $464 million, with Trump being liable for the vast majority at approximately $454 million.

The judgment carries an annual interest rate of 9 percent until it is paid, which means that the amount Trump owes is increasing daily by over $111,000. Although an automatic stay was granted for 30 days after the judgment was entered, this stay will expire on Monday, making it essential for Trump to take action.

To secure a stay while he appeals, New York courts require Trump to guarantee the entire amount, plus additional cash or security equal to 120 percent of the award. Trump's attorneys have acknowledged the difficulty of obtaining a bond large enough to cover the judgment, stating that it is a "practical impossibility." They have explored options such as taking out a large loan, selling off properties, or even declaring bankruptcy.

Trump has sought permission from the state Appellate Division to appeal while posting a reduced bond or no security at all. His attorneys argue that he possesses valuable assets and has the capacity to pay the entire judgment if necessary. They also emphasize the impossibility of secretly selling assets like Trump Tower. The appeals court may rule on Trump's request at any time, even after the deadline has passed. If the court rules against him, his attorneys have requested time to present their case to the state's highest court, the Court of Appeals.

The New York Attorney General's office has urged the appeals court to reject Trump's request, describing it as "extraordinary." They argue that Trump's difficulty in coming up with the cash raises concerns that he may attempt to evade or complicate the enforcement of the judgment. The office has pointed out that even billion-dollar judgments are typically fully bonded on appeal.

An appeals bond functions similarly to a bail bond in criminal court, requiring the person or company to put up cash and securities as collateral for the entire judgment. This collateral ensures that the judgment holder can collect if the appeal is unsuccessful, as legal challenges can be lengthy. Fees paid to the bond company may be lost if the person appealing is successful.

Trump's financial position primarily consists of real estate assets rather than liquid cash or stock. While his brand and a 2021 financial statement indicate considerable worth, the bulk of his assets are tied up in real estate. Trump claimed to have significant cash reserves during his deposition in the case last year, but it is likely that the amount has decreased, partly due to posting a $91 million bond in another defamation case recently.

Trump's attorneys have approached multiple surety companies for a bond but have encountered significant challenges in finding one willing to cover the massive amount required. Very few bonding companies are willing to consider such a magnitude, and those that do insist on cash or cash equivalents rather than accepting hard assets like real estate as collateral.

In response, the AG's office suggested that Trump could have used his properties as collateral even without a bond. They also accused Trump and his co-defendants of prolonging the process, noting that these issues could have been raised earlier.

One option for Trump to temporarily halt the deadline is to file for bankruptcy protection. However, this move could damage his image as a savvy businessman and potentially trigger defaults on existing bank loans. Legal experts have suggested that Trump could use smaller individual companies found liable to declare bankruptcy and trigger an automatic stay, but this would only apply to those companies, not to Trump personally.

As Monday approaches, the clock is ticking for Trump to take action. If he fails to do so, the New York Attorney General will be free to proceed with asset seizures without requiring further court orders. Trump's properties, such as Trump Tower and 40 Wall Street, are among the assets estimated to be worth hundreds of millions of dollars that could potentially be targeted.

The outcome of this high-stakes legal battle remains uncertain, and the decisions made in the coming days will significantly impact Trump's financial standing and future prospects.

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