Donald Trump's bond deadline approaches as New York AG prepares to seize former president's assets

NEW YORK -- Donald Trump's three-day deadline to find nearly half a billion dollars or risk seeing his cherished property empire dismantled building by building is creating one of the most extraordinary twists ever seen in a US presidential election campaign.

Trump's new drama concerns his struggle to come up with a bond to cover $464 million plus interest charges so that he can appeal a civil fraud trial judgment against him, his adult sons and his company. If he can't somehow find the money by Monday, New York Attorney General Letitia James may begin seizing some of Trump's assets to finance his obligation to the state. She has laid the groundwork with court filings that suggest Trump's Seven Springs estate and golf course in Westchester County, New York, could be among her first targets.

"The attorney general is ready to go. They are ready to go after his money to try to fulfill the judgment," Adam Leitman Bailey, a real estate attorney who sued Trump seven times, told CNN's Erin Burnett. "The question is how hard it is going to be to collect."

RELATED: Trump faces 'insurmountable difficulties' in securing $464M bond in civil fraud case

While this is primarily a crisis about Trump's business and personal wealth, it is creating real political implications given his status as the presumptive Republican presidential nominee. No other candidate has ever faced such a distraction in the middle of an election campaign - and that's separate from the former commander-in-chief's parallel constellation of criminal cases that will dominate the run-up to Election Day and potentially add to the tumult of his second presidency if he beats President Joe Biden.

Trump's increasingly alarmed posts on social media on Thursday offered a window into his desperation. And they showed how every one of his cases now has a similar defense. He claims he's not guilty of breaking the law but is the victim of endless political persecution. "ELECTION INTERFERENCE," Trump for instance wrote on his Truth Social network. He complained that putting up money to permit an appeal was "VERY EXPENSIVE." And he sent out a fundraising appeal to supporters titled "Keep your filthy hands off of Trump Tower!"

Even one of his legal cases would have been enough to drive any conventional candidate from the race long ago. But Trump leads many national and swing state polls, a sign that his attempts to spin his flurry of legal duress as persecution are working among many Republican voters. His standing in the race also reflects the daunting problems shadowing Biden's reelection bid as the unpopular president tries to convince Americans that a recovering economy is healthier than they perceive in their daily lives given expensive trips to grocery stores and the high interest rates that make housing and other major purchases so daunting.

While Trump's enemies would relish his property portfolio being gutted by James, the political impact of such a humiliation would be uncertain. The resulting furor might The resulting furor might add fuel to the ex-president's claims he is being unfairly targeted by Democratic prosecutors because of who he is. One of his closest allies, Rep. Elise Stefanik of New York, is already trying to foster such an impression by slamming what she claimed was a "fundamentally un-American"campaign against him. At the same time, however, the latest controversy surrounding Trump may begin to remind moderate Republican and independent voters of the daily chaos that characterized his years in office. The Biden campaign has long maintained this will inevitably shift voters the president's way, even if there is little evidence in the polls so far of that happening.

A long list of legal challenges

The ex-president's struggle to come up with funds, after multiple insurance firms declined to underwrite the bond, is a humiliating spectacle for a former president whose image as a masterful property magnate is central to his public brand. The frenzied search for money raises painful questions about the extent of Trump's liquid wealth about which he has long boasted. It's also an undignified plight for someone who could be occupying the White House in 10 months, and suggests troubling conflicts of interest if he turns to private donors - or overseas sources - to find the money in an 11th-hour dash for cash.

The implications of the rush to finance the bond have caused panic in the ex-president's inner circle, CNN's Kaitlan Collins reported this week. But as grave as it is, the drama around the bond payment is only one of the multiple perils confronting Trump.

- On Thursday, CNN reported that Fani Willis, the district attorney of Fulton County, Georgia, plans to push hard for a trial before November's election in a bid to thwart Trump's delaying tactics - despite narrowly escaping being thrown off her election interference case following an intimate relationship with a fellow prosecutor. Given the complexity of the racketeering case, which includes an array of former Trump associates as co-defendants, any such timeline feels wildly optimistic. "I really think this is mostly just posturing by the DA's office," Michael Moore, a former US attorney, told CNN on Thursday. And while Willis wants a trial date soon, she is still not completely secure. The judge who allowed her to continue on the case despite rebuking her conduct, has granted the defendants the right to appeal his decision.

- Elsewhere in Trump's multi-city legal quagmire, Judge Arthur Engoron, who oversaw the New York civil fraud case that Trump lost, imposed new constraints on the the Trump Organization by expanding the reach of the monitor who is providing court-ordered oversight. The move means the firm will not for instance be able to move large amounts of money or take any significant business steps without scrutiny - a departure for a company that has always played by its own set of rules.

- Also in New York, the Manhattan district attorney's office called on a judge to impose no further delay in the trial over Trump's payment of hush money to the adult film actress Stormy Daniels during the 2016 election campaign. The trial had been set to start on Monday but was postponed after new documents surfaced and the former president is now asking for a 90-day delay. Judge Juan Merchan has postponed the case at least until April 15 and is due to hold a hearing on discovery issues on Monday that could also produce a firm trial date.

- All of this is unfolding as other Trump trials - including federal prosecutions on election interference and the alleged mishandling of classified documents - are on hold as he tries to run out the clock ahead of November's election with frenzied litigation and the filing of appeals. The Supreme Court is due to hear his sweeping claim of presidential immunity for acts committed in office next month and a ruling is not expected until late June. The decision could have important implications for the criminal cases that Trump is facing as he seeks a second term.

- Yet, in one ray of light for the ex-president this week, his net worth could soon be set to soar with the merger of his media properties including the Truth Social network and Digital World Acquisition Corp., a blank-check firm. The move would make Trump by far the largest shareholder of the merged, publicly traded company and would on paper add billions of dollars to his net worth. In theory, this is the kind of windfall that could help Trump at a moment of extreme financial distress and at a moment when his campaign fundraising is falling well short of Biden's. In practice, however, conditions of a deal mean that the ex-president could not liquidate his shares to ease his cash crunch immediately. And if he were to sell, the price of the company's stock would likely tumble.

How James plans to extract the state's due from Trump

State lawyers filed judgments in Westchester County, north of Manhattan, on March 6 - a week after Engoron's civil fraud judgment finding that Trump, his adult sons and the Trump Organization had committed massive fraud, largely through overvaluations of property to secure favorable loans from banks and better rates from insurance companies.

The former president's lawyers disclosed this week that he had failed to find an insurance company to underwrite a bond that would guarantee the state's financial stake in the case while the appeal process plays out. Trump has already filed a nearly $100 million bond in another case, after losing a defamation claim to the writer E. Jean Carroll, which he also plans to appeal.

Trump's attorneys have warned that any attempt to sell off properties to meet the judgment would cause him permanent financial damage since buyers would demand "fire sale" prices."

There's also another reason why an attempt by James to seize his assets could be problematic for the ex-president - and is a far more complicated proposition for the attorney general than it might first appear.

Some of Trump's buildings and properties are sure to be financed by mortgages and other financial arrangements that will be difficult to unravel. In the event of a sale, the proceeds would go first to make good the lenders, meaning that a substantial chunk of the Trump empire may need to be sold off to reach the near half billion dollar figure owed to the state.

One option that Trump might be forced to consider is bankruptcy - a route he has used several times in his flamboyant and checkered business career and that may allow him to dispose of assets in an organized way. But Collins reported this week that he has privately expressed opposition to that path, and it remains the least likely way out for now.

Ultimately, the stigma of enduring such a process so close to a general election might be too much for the ex-president to bear. And it would add to concerns that the former president isn't fit for a return to the Oval Office.

Whatever the resolution, the multiple dramas again strike at the question at the heart of this election: Do Americans really want four more years of the mayhem, scandal and challenges to the law that rage around the former president week after week?

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