Former President Donald Trump is facing one of the biggest financial hurdles of his life: coming up with a $464 million bond to appeal the massive judgment against him in New York’s civil fraud case. But according to his lawyers, finding an insurance company willing to underwrite that bond has been nearly impossible.
No One Wants to Back Trump’s Bond
Trump’s legal team has reportedly approached at least 30 different underwriting companies, and not a single one has agreed to back a bond of that size. The main issue? Most bonding companies are simply unwilling to cover an amount that enormous—especially without hard cash to secure it.
According to court documents, insurance broker Gary Giulietti, who testified in Trump’s defense during his civil fraud trial, stated that securing a bond of this size is “a practical impossibility.” The problem is that insurance companies are looking for liquid assets—cash or stock—not real estate. And while Trump has repeatedly insisted that his properties are worth far more than the judgment against him, that’s not enough to satisfy potential underwriters.
This means that unless Trump finds a way to post the bond, the New York attorney general’s office could start seizing his assets, including some of his most prized real estate holdings.
Trump’s Lawyers Push for More Time
In response to the situation, Trump’s attorneys have asked the appeals court to delay the bond requirement until his case is fully resolved. They argue that since Trump’s real estate empire is worth billions, there’s no real risk of him not being able to pay if he ultimately loses his appeal.
If that request is denied, Trump’s lawyers are asking for an additional delay—this time until the New York Court of Appeals, the highest court in the state, hears his case. If they don’t get that extension either, Trump could be in serious trouble.
Trump Calls the Bond “Unconstitutional”
Trump himself has been vocal about his frustration with the situation. Taking to his social media platform, Truth Social, he called the bond requirement “unconstitutional, un-American, unprecedented, and practically impossible for ANY company.”
“The bonding companies have never heard of such a bond, of this size, before,” he wrote, “nor do they have the ability to post such a bond, even if they wanted to.”
It’s not the first time Trump has claimed legal rulings against him are politically motivated, but the reality is that this is a standard legal requirement for appealing a civil judgment of this magnitude. Without the bond, New York Attorney General Letitia James has the legal authority to start collecting the money Trump owes.
The Origin of the $464 Million Judgment
The massive financial penalty stems from a civil fraud case brought by Letitia James, who accused Trump of inflating his net worth to secure better loan and insurance terms. Judge Arthur Engoron ruled against Trump last month, ordering him to pay $355 million in “ill-gotten gains.” After interest and additional penalties, the total amount ballooned to over $464 million.
The court found that Trump and his co-defendants—including his adult sons, Donald Trump Jr. and Eric Trump—engaged in fraudulent business practices for years. They allegedly exaggerated the value of Trump Organization properties to mislead banks and insurance companies, gaining access to better financial deals than they otherwise would have received.
Engoron’s ruling was clear: Trump and his company manipulated financial records to create the illusion of greater wealth. The result? A hefty penalty designed to strip Trump of the financial benefits he allegedly obtained through deception.
Why Posting a Bond is Crucial
Trump is appealing the decision, but here’s the catch—New York law requires him to post a bond for the full amount of the judgment if he wants to delay enforcement while he fights the ruling. This means that, even if he ultimately wins on appeal, he still has to put up the money now.
If he doesn’t post the bond, the state can move forward with collection efforts. That could include freezing his bank accounts, placing liens on his properties, and even initiating asset seizures.
Trump’s Other Legal Woes Add to the Pressure
This is just one of many legal and financial problems Trump is currently facing. Earlier this month, he managed to post a $91.6 million bond in his defamation case involving writer E. Jean Carroll. That case alone required significant financial maneuvering, and it was backed by insurance giant Chubb. However, Chubb reportedly won’t touch the civil fraud case bond, further complicating Trump’s efforts.
Insurance broker Gary Giulietti explained that most major underwriters simply won’t issue bonds exceeding $100 million—let alone nearly half a billion. “Even the largest insurance companies in the world aren’t comfortable securing a bond of this size,” he said, adding that Trump would likely need to come up with over $550 million in cash to cover the bond, including fees and interest.
Can Trump Come Up With the Money?
Trump’s financial situation is notoriously difficult to assess. He frequently claims to be a billionaire, but much of his wealth is tied up in real estate. Selling off properties quickly isn’t easy, especially with a deadline looming at the end of the month.
Some legal experts believe Trump may need to sell off key assets or take out massive loans to come up with the money. Others speculate that he could try to negotiate a deal with the attorney general’s office—though James has shown no indication that she’s willing to back down.
Trump’s Camp Calls It Political Persecution
Predictably, Trump’s campaign is framing the judgment and the bond requirement as a politically motivated attack. His spokesperson, Steven Cheung, slammed the ruling as an “abuse of the law” and part of a broader effort by President Joe Biden’s administration to take down Trump ahead of the 2024 election.
“President Trump will continue fighting and beating all of these Crooked Joe Biden-directed hoaxes and will Make America Great Again,” Cheung said in a statement.
While Trump’s supporters may buy that argument, the reality is that this is a civil fraud case brought by the state of New York—not the federal government. And despite Trump’s repeated attacks on Judge Engoron, the case has been playing out in a state courtroom, far removed from Biden’s Justice Department.
What Happens Next?
The clock is ticking. If Trump can’t secure the bond before the deadline, the New York attorney general could start seizing assets—potentially putting some of Trump’s most iconic properties at risk.
Will Trump find a way to come up with the money? Will the appeals court grant him more time? Or will we soon see the state of New York taking action to collect what’s owed?
One thing is certain—this legal battle is far from over. Trump’s financial empire, political future, and personal brand are all on the line. And as the deadline approaches, the pressure is mounting.
Stay tuned, because this saga is only getting started.
