TRUMP PANICS as Lawyers Admit $464 MILLION Bond Is “Impossible”

Added: 2026-05-18

[00:00:00]And we're following breaking news just coming into CNN right now. Attorneys for former President Donald Trump say they're unable, unable to get a bond to pay the $464 million fraud judgment, calling it, and I'm quoting now, a practical impossibility. CNN's Kara Scannell is joining us from New York right now. Kara, what can you tell us?

[00:00:21]Walk us through what this means.

[00:00:23]So, Trump's lawyers have informed the appeals court today that they are unable to get anybody, an insurance company and underwriter, to help them post this bond, the $454 million for Trump alone, the rest to cover his sons. And what they say is that they've approached 30 of insurance underwriters, some of these big gigantic companies that you know, and they say that none of them are willing to do it. As you said, they're calling it a practical impossibility.

[00:00:49]You know, one of the reasons that they say is an issue here is that some of these insurance companies have internal limits that they won't issue a bond for more than $100 million.

[00:00:58]March 18th, 2024.

[00:01:00]The anchor introduces a filing just received from Trump's legal team directed to the New York Appellate Division. The subject, Trump's attorneys have informed the appeals court that they are unable to post the bond required to stop New York Attorney General Letitia James from seizing his assets while he appeals the Engoron civil fraud judgment. The number in the filing is $464 million, $454 million for Trump himself, the remainder for his sons Don Jr. and Eric. Donald Trump's lawyers say he's been unable to obtain a bond for the $454 million he owes as part of a civil fraud judgment against him, his elder sons, and his company. He's asking a New York state appeals court to pause the judgment against him while he appeals.

[00:01:44]Well, let's cross live now to New York and speak to our North America correspondent Nada Tawfik, who is there for us. Nada, what exactly is this all about?

[00:01:54]Yeah, well, Miriam, when Donald Trump was ordered to pay these massive amounts in two consecutive civil judgments, many questioned if he had the cash to do it.

[00:02:02]Now, earlier this month, he did post a 91.6 million-dollar bond in the E. Jean Carroll defamation case, but as you said there, today his lawyers have said he's been unable to obtain a bond in the much larger civil business fraud judgment against him. The structure of the problem is this.

[00:02:21]On February 16th, 2024, Judge Arthur Engoron issued his final judgment in the New York civil fraud case. 35486868 in disgorgement $6 million in pre-judgment interest totaling more than $453 million for Trump and an additional approximately $10 million for his sons and Allen Weisselberg. When Trump appealed the judgment on February 26th, a 30-day automatic stay of the judgment took effect, during which James could not yet move to seize assets. That stay expires on March 25th, 2024. To keep the stay in effect past March 25th to stop James from beginning the collection process while the appeal plays out, Trump is required by law to post a bond securing the full judgment amount. The bond is not payment. It is a guarantee proof to the court that if the appeal fails, the money will be there. The bonding company, the surety, guarantees the judgment amount, charging Trump a fee for the service. If the appeal is lost, the surety pays the court. If the appeal is won, the judgment is vacated and the surety pays nothing. This is how the appellate bond system works in every civil case in New York. Well, what are we talking about? Where did this start?

[00:03:28]Where does this dollar figure come from?

[00:03:30]>> Yeah, John. So, let's go back to the beginning. This case is the civil lawsuit filed by the New York State Attorney General Letitia James against Donald Trump and his companies alleging and now having proved that they overinflated their assets and then used that in order to get loans from banks.

[00:03:44]Now, the judge returned a verdict for Donald Trump. The verdict was in the amount of $355 million plus interest. You somehow did the math and backed it out is what gets us to that $450 plus million dollar figure.

[00:03:59]Now, the Attorney General can start collecting on that as of Monday unless Donald Trump posts a bond with the court. Now, let's understand exactly what that means. There's sort of a two-step calculation going on here.

[00:04:11]First of all, a bonding company.

[00:04:13]Usually, this is going to be a private company, an insurance company, or a bank. They certify to the court that if Donald Trump does not pay the total amount that he's owed after his appeal, we are good for it. We will cover him.

[00:04:26]Now, in order for them to make that promise, Donald Trump has to post collateral with the bonding company.

[00:04:32]That can be cash, that can be other assets. Now, Donald Trump has been unable to do that so far and hence, if we get to Monday and he's not posted a bond, Letitia James can start collecting. The problem is size. Trump's total bond obligation, $454 million for his portion, plus the sons' amounts, plus interest accruing at $112,000 per day since the judgment, comes to more than $464 million and growing. By the time of the filing with fees and interest, the insurance broker retained by Trump to find coverage, Gary Giulietti, estimated the total at more than $550 million when shitty fees are included. Giulietti signed an affidavit for the court filing. His core statement after substantial good faith effort over the last several weeks, obtaining an appeal bond for the judgment amount of over $464 million is just not possible under these circumstances. Giulietti said he had been directly or indirectly involved in the issuance of thousands of bonds over his career and had never heard of nor seen an appeal bond of this size for a private company or individual. He said Trump's team had approached approximately 30 surety companies through four separate brokers. What Costello explains from New York is why the 30 NOS's are not surprising to anyone in the insurance industry even though they appear to be a surprise to the Trump legal team. There are two structural barriers. First, scale. Only a small number of bonding companies are approved by the US Treasury Department to underwrite bonds of any size. Among that group, many have internal policies limiting their maximum exposure on a single bond to $100 million.

[00:06:05]A half-billion-dollar bond is simply not a product that most of these companies offer. Gillette's affidavit notes that bonds of this size, when they exist at all, are issued to the largest public companies in the world, not to individuals or privately held businesses. The Trump Organization is privately held. Even under the most favorable circumstances, the pool of underwriters capable of writing a $464 million bond is tiny. Second, collateral. Trump has real estate. He has iconic properties. He has what his campaign spokesman called assets worth more than the judgment.

[00:06:39]What he apparently does not have in sufficient liquid form is the cash, stocks, and bonds that surety companies require as collateral backing a bond of this size.

[00:06:49]Well, in my experience, uh real estate developers tend to be very highly illiquid. They tend to be highly leveraged. They tend to have all sorts of loans. They, you know, they might have a revolving line of credit. They may have uh various loans and personal guarantees out there. Um however, uh what I will say is that, you know, this is not a complete surprise to Donald Trump. It's not like the New York Attorney General's case happened over the course of minutes. It happened over the course of years. Uh and Trump could anticipate a potential judgment. And the fact that he hasn't prepared by refinancing and making selling properties and so on suggests that he may be less wealthy than he has portrayed himself. Costello explains the distinction carefully. Underwriters want liquid assets, cash, publicly traded securities, instruments that can be converted to money quickly and at a known value if the bond is called.

[00:07:43]Real estate is the opposite of liquid.

[00:07:45]It's value is contested. It's sale takes months or years and its valuation is subject to exactly the kind of dispute that produced the underlying fraud judgment in the first place. Insurance companies, Castello notes, also face regulatory constraints. State insurance regulators limit the premiums they can charge for taking on real estate risk, which means they cannot price real estate collateral in a way that makes business sense for half billion dollar bond. Alan Garten, the Trump organization's top legal officer, described the no real estate rule as a major obstacle in his own sworn statement to the court. And some of the biggest names that you can think of in the insurance world also will not underwrite a bond and take property, which is what Trump has to put up. They want cash. They want securities, stocks, bonds, something that is what's a liquid, easy to sell asset. They don't want property. And so that is the problem that Trump has run into in trying to come up with this massive amount of money, half a billion dollars.

[00:08:42]You know, these bond companies, too, they also want uh their own, I guess you could call it, you know, insurance on it. They want extra money than just what the bond is so that they can, you know, cover this as it as it plays out. This bond is to uh stop the New York attorney general's office from seizing the property while the appeal of the judgment and the case goes forward. So, they've been asking the the Trump's team has been asking the appeals court to allow them to not have to post this bond um until the appeal is over. Or they're saying the filing's formal request to the appellate division is that the court allow Trump to forego posting the full bond pending the appeal waving or dramatically reducing the bond requirement on the grounds that Trump's real estate holdings greatly exceed the amount of the judgment, that those properties are impossible to secrete or dispose of surreptitiously, and therefore that James is effectively secured during the pendency of an appeal even without a a bond. This is a legal argument with some surface plausibility.

[00:09:39]If the properties exist, cannot be hidden, and are worth more than the judgment. What is the practical risk to James of allowing the appeal to proceed without a bond? The counter argument which James' office has made consistently is that the bond requirement exists precisely to prevent the asset owner from depleting, encumbering, or transferring assets during an appeal. Actions that are harder to reverse than they are to execute. A building that is remortgaged, transferred to a new corporate entity, or subjected to additional liens during a multi-year appeal process may look different at the end of that process than it did at the beginning. The bond requirement is the legal system's protection against that risk. Waving it for Trump would create a precedent that appellants with high value, but illiquid assets can avoid bond obligations by arguing their properties provide adequate security. A precedent with broad implications for civil judgment enforcement. Before the filing, Trump had already raised the bond issue publicly on Truth Social.

[00:10:35]He wrote that the bond requirement was unconstitutional, un-American, unprecedented, and practically impossible for any company, including one as successful as mine.

[00:10:46]The capitalized any company is a rhetorical claim that the financial problem he faces is not specific to him, but inherent to the size of the judgment. The implicit argument being that if the judgment is so large, no one can post bond for it. The judgment itself must be excessive. This framing aligns with his lawyers' separate argument that the $454 million penalty violates the Eighth Amendment's prohibition on excessive fines. The argument that eventually succeeds at the Appellate Division in August 2025, when the court throws out the entire financial penalty. Trump's lawyers had previously asked for the bond to be reduced to $100 million, a request James' office opposed. The March 18th filing escalated. They are now asking for no bond at all. The Appellate Division must decide by March 25th, when the automatic stay expires, whether to grant that request, reduce the bond, or deny it entirely and allow James to begin collection. If James begins collection, the tools available to her are significant. She has said publicly, including in a direct interview with ABC News, that she is prepared to move immediately. She has looked at 40 Wall Street from her Manhattan office window and said so publicly. The enforcement tools she can deploy include seeking court orders to freeze Trump's bank accounts, imposing restraining notices on the tenants of Trump-owned buildings, redirecting their rent payments to the New York County Sheriff rather than to the Trump Organization, subpoenaing Trump's personal financial records, and ultimately requesting that the Sheriff auction Trump's properties. The auction process, particularly for trophy commercial real estate, would take months and involve additional court proceedings. Trump's lawyers would file objections, delay motions, interlocutory appeals, but the process could begin within days of the March 25th deadline if the Appellate Division does not act.

[00:12:34]The $91.66 million reference in the filing is the bond Trump had successfully posted 2 weeks earlier on March 7th, 2024, through Chubb Insurance covering the separate E. Jean Carroll defamation judgment. That $91.6 million bond was difficult to arrange, but ultimately possible with Chubb agreeing to take the risk. The Carroll bond succeeded because $91 million, while large, is within the range that major underwriters can handle. The Engeron bond at $464 million is more than five times larger. Chubb, according to Alan Garten's sworn statement, explicitly told the Trump Organization that it could not write the Engeron bond. It was beyond their capacity. The Carroll bond was the ceiling, not a template for what was possible at higher amounts. The structural paradox at the center of the filing is one that Costello's reporting frames precisely. Trump has real estate assets he claims are worth billions of dollars. He has told courts, banks, and insurers for decades that his properties are worth enormous sums. And yet, in the moment when he most needs those asset valuations to function as financial instruments, as collateral for a bond, as security for a half-billion-dollar judgment, they cannot be converted to cash or accepted as security by the insurance market. The man who spent years inflating his asset values on financial statements is now in a situation where those inflated assets, even if accepted at face value, cannot serve the financial function he needs them to serve. The judgment he is trying to appeal was the consequence of using inflated valuations to obtain favorable financial treatment. The bond crisis is, in a structural sense, the consequence of the same underlying illiquidity that made the fraud possible. If Trump had genuinely liquid assets matching his stated net worth, he would not be in this position.

[00:14:20]Letitia James, in her ABC News interview, was precise and direct. "We are prepared to make sure that the judgment is paid to New Yorkers. And yes, I look at 40 Wall Street each and every day. The image is deliberate." 40 Wall Street, Trump's lower Manhattan office tower, a building he has owned since 1995 and used as a flagship of his New York real estate portfolio, sits within sight of the New York Attorney General's office. James is saying, "I can see it. I know where it is. I am watching." The choreography of the civil fraud case, from Engoron's ruling to Trump's response to Scandals Live calculation to this bond filing to James's window view of 40 Wall Street, has been conducted in the most public possible way. A legal process about a public man's financial statements played out in public in New York, where the buildings are visible and the courtrooms are accessible and the filings are public record.

[00:15:10]What happens next from the March 18th filing?

[00:15:13]On March 25th, 2024, the Appellate Division, a five-judge panel of the First Department, issues an order. They grant Trump a bond reduction, cutting the required amount from 464 million to 175 million. No written opinion is issued at the time explaining the reasoning. Trump has 10 days to post the 175 million bond. He posted on April 5th, 2024 through a relatively obscure California-based surety company called Knight Specialty Insurance. The 175 million-dollar bond secures the stay.

[00:15:46]James cannot proceed with collection while the appeal continues. The Appellate Division appeal itself grinds on through 2024 and into 2025. In August 2025, the court issues its ruling on the merits. The financial penalty is thrown out as an unconstitutional excessive fine under the Eighth Amendment, though the underlying fraud finding is upheld.

[00:16:06]James appeals that ruling to New York's highest court, the Court of Appeals. The case, as of early 2026, is not over, but on March 18th, 2024, none of that is known. What is known is this: Trump's lawyers filed papers saying they cannot post a bond for half a billion dollars, calling it a practical impossibility.

[00:16:25]Carol Costello in New York explains why the insurance market cannot accommodate the request. The clock says 1 week, and Letitia James is looking at 40 Wall Street. This is Daily News Minutes. Stay with it. Gary Giuletti, the insurance broker whose affidavit forms the backbone of the practical impossibility filing, is not a neutral industry expert retained for this purpose alone. He testified as an expert witness for Trump during the civil fraud trial itself. He is, according to Judge Engoron's own finding in the trial record, a close personal friend of Trump's who has a financial interest in the outcome of the case. The trial judge specifically noted this in his ruling as a reason to view Giuletti's expert testimony with skepticism. Now, the same broker who gave expert testimony for Trump at trial is providing a sworn affidavit for the bond filing. The same man with the same established personal relationship making the same kind of argument about the impossibility of Trump's financial situation. This is not automatically disqualifying. A broker who knows Trump's financial situation in detail is in one sense precisely the right person to testify about the market's response to a bond request, but the circularity is notable. The expert saying no one will write the bond is the person Trump brought in to try to get the bond written, who also happens to be a close personal friend of Trump's with a financial interest in the appeal succeeding. The regulatory structure of the shy bond market, which Costello's report touches on, and which explains the $100 million cap problem, is worth laying out in full because it illuminates why the crisis is structural rather than a function of Trump's particular unpopularity with insurers.

[00:18:01]The US Treasury Department maintains a list of approved corporate sureties, companies authorized to write bonds for federal proceedings. States have their own approval processes. For a civil judgment as large as Engoron, the bond would need to go through the highest tier of Treasury-approved companies.

[00:18:18]Among those companies, the practical limit on a single bond exposure is typically set by internal risk management policies. Companies that will write bonds up to a certain size as a matter of standard practice and decline beyond that because the concentration of risk in a single obligation creates regulatory and solvency concerns.

[00:18:36]Insurance regulators require companies to maintain sufficient reserves to cover their obligations. A $500 million single bond exposure requires an enormous reserve commitment. And for most surety companies, the economics simply don't work. For publicly traded corporations, the Fortune 500 companies that Giulietti references, very large appeal bonds can occasionally be written because those companies have transparent public financials, liquid publicly traded stock that can serve as collateral, and ratings agencies that certify their creditworthiness. The collateral problem is solved by stock. A publicly traded company can post shares as security for a bond because shares are liquid and their value is established by market trading every business day. Trump's business is privately held. Its assets are real estate. Real estate as a bond collateral type fails on both dimensions. It is illiquid, cannot be sold quickly at a certain price, and its value is contested. The anger in judgment was literally about the fact that Trump's real estate values had been fraudulently inflated. An underwriter being asked to accept Trump's real estate as collateral for a $464 million bond is being asked to accept a security the exact assets whose valuation was the subject of the lawsuit. Assets that a court has just found were systematically overvalued in financial statements. The conflict is almost poetic. The assets that generated the fraud judgment cannot serve as collateral for the bond that would stay enforcement of that judgment because their value is precisely what is in dispute.

[00:20:07]The Trump Organization's corporate structure adds a further layer of complexity to any collection or enforcement scenario. Trump's real estate holdings are owned through an intricate network of limited liability companies, separate LLCs for each property, with holding companies above them, managed entities, partnership interests, and leasehold structures. 40 Wall Street, for instance, is a leasehold arrangement. Trump holds a long-term lease on the building rather than owning it outright, which means any sheriff's enforcement action would need to deal with the leasehold interest rather than the fee simple ownership.

[00:20:41]Mar-a-Lago operates under deed restrictions that limit its use and assailable value. Trump Tower's commercial floors are held through structures that separate the retail from the residential from the management company. Any collection process, even after an appellate court affirms the judgment, would require navigation of this corporate maze. You can't just say, "It's Trump Tower, so I'm going to take it." One New York judgment enforcement attorney told ABC News, "The legal architecture that Trump used for decades to manage assets and limit liability is in this moment both an obstacle to collection and a partial explanation for why he cannot produce liquid assets adequate to a $464 million bond."

[00:21:22]Trump's public claim throughout this period stated in truth, social posts, in statements from his campaign, and in statements from his lawyers, is that he has hundreds of millions of dollars in cash. Specifically in the period of the trial and the judgment, Trump repeatedly asserted he was sitting on $400 million or more in liquid assets. If this is true, if Trump genuinely had $400 million in cash or cash equivalents, the bond crisis should not have existed. A man with $400 million in cash can post a $454 million bond through a shy company that takes the cash as collateral or can simply pay the judgment directly. The fact that he is filing papers saying a $464 million bond is a practical impossibility is at minimum intention with his stated cash position. His lawyers' explanation that the cash exists, but that no underwriter will take his real estate sidesteps the obvious question of why the cash itself, if it exists, cannot serve as collateral for the bond. The answer apparently is that his $400 million in claimed cash would not cover the full $464 million plus the Shays' fees and reserve requirements, which Giuliani estimated would push the total past $550 million.

[00:22:34]The gap between $400 million and $550 million is real, but it also raises the question of whether the $400 million cash claim was itself accurate. A question that goes to the heart of the underlying fraud case, which was about the accuracy of Trump's representations about his financial position. The Carroll comparison is relevant and the filing itself invokes it. The $91.66 million bond Trump posted through Chubb to stay the E. Jean Carroll defamation judgment was the largest bond Chubb was willing to write for Trump in that period. Alan Garten's sworn statement in the Engoron bond filing confirms that Chubb explicitly told the Trump organization it could not write the Engoron bond. The Carroll bond had exhausted Chubb's appetite for Trump exposure.

[00:23:18]This detail matters because it reveals the ceiling. Even Trump's most successful recent bonding relationship had a limit that the Engoron judgment blew past immediately. The Carroll judgment at 83.3 million was on its own a historically large defamation award.

[00:23:33]Engoron is more than five times larger.

[00:23:36]The insurance market, which accommodated the Carroll judgment at the outer edge of what it could manage, simply cannot scale to Engoron. The broader story of what the bond crisis means for Trump's claim to be a successful billionaire is a story the legal proceedings have been telling in detail since 2022 and that this filing crystallizes. Trump has spent his entire public career projecting wealth towers with his name in gold properties described in his own financial statements as worth hundreds of millions or billions. A brand built on financial success as evidence of leadership competence. The civil fraud case was specifically about the gap between that projected wealth and the actual numbers on financial statements submitted to banks.

[00:24:16]The bond crisis is a live demonstration of that gap. Whatever Trump's nominal asset values are, the liquid financial capacity that actual billionaires have access to, the ability to write a 500 million dollar check or to pledge 500 million dollars in publicly traded securities or to arrange a bond against a 500 million dollar cash position is apparently not available to him.

[00:24:39]The insurance market, which is in the business of assessing real financial capacity rather than nominal valuations, has responded with 30 consecutive rejections. The outcome that eventually resolves the crisis, the appellate division reducing the bond to 175 million dollars and Trump posting that amount through Knight Specialty Insurance is a temporary solution to a structural problem. Knight Specialty is not one of the major insurance companies Gillette he was approaching. It is a smaller California-based specialty insurer. It's willingness to write the 175 million bond on terms that have not been fully made public is either a testament to Knight's risk appetite or as some insurance industry analysts noted at the time, a reflection of the reduced amount making the risk manageable where the full amount was not. The 175 million-dollar reduction, cutting the required bond by more than 280 million with no written explanation from the court, was itself legally unusual. Courts reducing bond requirements by that magnitude in high-profile cases typically issue written opinions explaining the basis for the reduction. The first department's order was silent on its reasoning. The practical effect, Trump's asset seizure was avoided. The appeal could proceed and the clock continue to run. Carol Costello reporting from New York on March 18th, 2024, is standing at the beginning of a week that will determine whether the most significant civil fraud judgment ever entered against an American politician can actually be collected. She explains the bond market, the collateral problem, the 30 rejections, and the March 25 deadline. The filing is a legal document, but it is also a financial portrait of a man who has always claimed to have more money than anyone could count, facing a bill he says he cannot pay. This is Daily News Minutes. Stay with it.