Legal consequences are harsh and painful when they finally arrive in Trump’s orbit

Analysis by Stephen Collinson, CNN

Donald Trump is a master at postponing legal accountability, but two cases targeting the ex-president and his orbit now in the penalty phase show that when the law finally exacts its price, the experience can be harsh and humiliating.

Trump’s lawyers said Monday that he cannot secure a bond to cover a near half billion dollar judgment against him in a New York fraud case while he appeals. The admission is a dent to the mystique of an ex-president who built his brand on the power and size of his “The Art of the Deal” fortune. And it raises the possibility his cash crunch could worsen a growing personal and campaign financial crisis.

And Peter Navarro, Trump’s former trade guru, is headed to prison after failing in his plea for the Supreme Court to spare him jail while he appeals a conviction for ignoring congressional subpoenas for documents and testimony about his boss’ bid to overturn the 2020 election

Both cases offer a lesson in the potential consequences of the culture of rule-breaking and a sense that pervades Trump world that the law is something that applies to other people. They also show that while defiance of laws and customs can be a potent political tool for the ex-president and his advisors, the outcomes of prosecutions designed to enforce more stringent codes of behavior can impose painful legal consequences regardless of politics. In Navarro’s case, his plight as a 74-year-old who is readying himself for the scary prospect of prison highlights the sometime price of loyalty to Trump and the ex-president’s method of turning every legal challenge into a political cause to boost his brand and goals.

Dramas over Trump’s latest legal struggles and his former advisor’s fight to stay out of jail again show how the former president and his associates use every single avenue of potential appeal — protections guaranteed to them by the Constitution and legal system Trump often decries — to postpone legal outcomes. This tactic has helped Trump get closer to one 2024 goal as his frenetic litigation has succeeded in delaying his criminal legal trials to the extent that it’s not certain that he will go before a jury before November’s presidential election. But for all the delays and digressions, the law, in the end, can be relentless. And while it has become a new normal to see a presumptive presidential nominee constantly embroiled in courtroom dramas, another set of legal imbroglios surrounding Trump and a high-profile member of the Make America Great Again movement is also a reminder of the surreal circumstances of the 2024 election.

Trump’s struggles to secure a bond highlight his financial situation

Trump has been trying to find an insurance company to underwrite his bond for at least $464 million dollars plus interest pending the appeals process after he, his adult sons and the Trump Organization were found liable for huge sums in ill-gotten gains in a civil fraud trial brought by the state of New York. Multiple insurance firms have balked at Trump’s attempt to finance the bond based on the value of his real estate assets. His tactics appear to indicate he lacks sufficient cash or shares to guarantee the agreement to cover disgorgement payments and interest payments on his own. The payment is required since an appeal could drag on for years and the state wants certainty that it will be paid if the court rules in its favor.

The former president argues that the value of his properties, including skyscrapers and golf resorts, vastly exceeds the size of the bond and therefore the court should allow him to defray payment until after the appeals process. This argument is richly ironic since it follows a case in which Trump was accused of hyping the value of his buildings to gain preferential rates from banks and insurance firms.

“This is somebody who is in this unenviable position because he has been found guilty of over inflating the values of his properties, so it makes sense insurance companies would not accept the properties and his valuations of them as security on a bond of this size,” former FBI deputy director Andrew McCabe told CNN’s Wolf Blitzer. Judge Arthur Engoron ruled last month that Trump and his co-defendants were liable for fraud, conspiracy and issuing false financial statements and false business records.

Post trial action in this case also hints at the darkening reality of Trump’s position and the way in which his fortune and empire appears to be in grave peril from the case. New York Attorney General Letitia James has said she will seek to seize some of his assets if he can’t pay what he owes. “Yes, I look at 40 Wall Street each and every day,” James told ABC News last month, referring to one of the ex-president’s most cherished Manhattan properties.

In another irony, there are increasing signs that for all his strength in polls, Trump has money problems. He’s already had to post bond of more than $90 million pending an appeal after he lost a second defamation case to the writer E. Jean Carroll. And his multiple cases, including four looming criminal trials, have saddled him with huge legal bills. The use of some of the cash from his political fundraising committees to meet those costs threatens to worsen an emerging cash disadvantage to President Joe Biden and the Democrats in the run-up to November.

As always with Trump, there is a legal front and a political one. It does not seem likely that signs he’s not as rich as he claims could undermine his business legend, which many supporters at his rallies still cite as qualification for the Oval Office. Nothing has weakened the ex-president among the hardest core of his support, and his effort to portray the multiple criminal and civil prosecutions that he’s facing as examples of political persecution have been a great success, helping him dominate the GOP primary race by consolidating base voters around his narrative. Trump argues that he’s protecting millions of Americans who would otherwise face victimization from the government. His claims are inaccurate but appear to be politically effective among his supporters who revile political and legal elites in Washington. Recently, he’s even drawn analogies between his legal situation and unfair treatment of minorities by the criminal justice system as he seeks to drive down Biden’s support among Black voters who form a critical part of the Democratic coalition in swing states.

Given the sensitivities of an election year, an attempt by James, who Trump has already complained is biased against him, to seize his properties would cause an extraordinary political furor. The process of seizing assets is legally complex at the best of times. It would likely be even more so given the labyrinthine financing used by Trump in his business. And the former president would certainly highlight his treatment to super charge his claims he’s a victim of a political witch hunt to keep him out of the White House. Therefore, there are good reasons why James – a Democrat –may seek other legal remedies to secure the judgment.

Trump is already trying to weaponize his latest legal liabilities. The presumptive Republican nominee said on Truth Social that a bond of this size is “unConstitutional, un-American, unprecedented, and practically impossible for ANY Company, including one as successful as mine.” “We will fight and defeat this Hoax, and all of the other Crooked Joe-directed Hoaxes, once and for all. If I wasn’t running for President of the United States, and leading by a lot, this kind of Witch Hunt would never have happened,” Trump said, seeking to highlight a question that has long surrounded this case – whether another businessman would have had the same treatment if he lacked the ex-president’s profile.

Trump does have some other options – for example, he could refinance or sell some of his diverse portfolio to put up the money. In court papers Monday, Trump’s lawyers accused James of being inflexible and argued that posting a full bond for a judgment of this size was a “practical impossibility.” They also warned that if he was forced to divest his properties, Trump would become victim to a “fire sale” that would cause massive lossesThe ex-president says the court has the authority to stay the judgment until after the appeal plays out.

While Trump was fighting on multiple fronts, Navarro Monday was contemplating the nightmare of jail time as soon as Tuesday after Chief Justice John Roberts rejected his last-ditch effort to stay free.

Navarro had argued that a federal judge’s refusal to let him raise an executive privilege defense at trial was wrong and that since an appeals court could reverse the decision he should remain out of prison. But Roberts wrote in a brief order that he had no basis to disagree with the lower court finding that Navarro had forfeited any argument that he could avoid appearing before Congress even if he was entitled to the privilege.

Peter Navarro, a former advisor to former US President Donald Trump, speaks to reporters as he departs the E. Barrett Prettyman Courthouse on January 25, 2024, in Washington, DC.

Navarro is expected to report to the minimum-security federal Bureau of Prisons satellite camp in Miami and become the first former White House official ever jailed for contempt of Congress. “He’s nervous,” Navarro’s prison consultant Sam Mangel told CNN. “Anybody, regardless of the length of their sentence, is going into an unknown world.” Navarro was sentenced to around four months in prison but is expected to be eligible for early release.

Although his case is historic, Navarro is far from the only ex-Trump associate to serve time in jail. For one of the most famous, there is apparently the possibility of an unlikely comeback.

Trump’s team is considering bringing back his former 2016 campaign chairman Paul Manafort to help with the Republican National Convention in Milwaukee this summer, CNN’s Kristen Holmes reported. The possibility of his return was first reported by the Washington Post.

Manafort was released from jail to home confinement during the Covid-19 pandemic in 2020 after serving about a third of a 7.5 year termHe was convicted of financial crimes in a case arising from special counsel Robert Mueller’s Russia probe and was eventually pardoned by Trump.

Meanwhile, legal controversies continue to swirl around a host of lesser-known Trump operatives due to the former president’s reckless behavior. In a Michigan-related case, Stefanie Lambert, a pro-Trump lawyer who tried to overturn the 2020 election, was arrested in a dramatic courtroom scene on Monday following a court hearing about her recent leak of internal emails belonging to Dominion Voting Systems.

This story has been updated with additional details.

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