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Former president Donald Trump has always had a pile of litigation trailing behind him.
He built his political persona on a narrative of self-made success before he descended his beloved golden escalators to launch his campaign for the presidency, suing and settling his way into office and through decades of “deals” on which he built a brand.
But a months-long trial and a devastating ruling against him on 16 February have pierced the long-running story he tells himself and others, one used to boost his national profile and seduce millions of voters.
A three-year investigation ended with a crushing verdict dealing more than $355m in penalties against him and his entities, an immense figure that, with interest, explodes to $454m, which will only keep growing every day until it’s paid.
The judgment threatens to drain his cash on hand, his ability to keep doing business in his home state, and the future of the company and his real estate portfolio that he has wrapped his fortunes and family into.
Judge Arthur Engoron’s ruling also comes just days after a federal jury’s $83m verdict for his repeated defamation of E Jean Carroll, on top of $5.5m he already owes her for lying about sexually abusing her. Last year, two Trump Organization subsidiaries were also fined more than $1.6m after a jury found the company guilty of more than a dozen charges stemming from what prosecutors described as a 15-year fraud scheme.
The former president has a small army of attorneys across the country, fighting even more lawsuits and dozens of criminal charges in New York, Florida, Georgia and Washington DC, with Trump-connected political action committees dumping out tens of millions of dollars on his attorneys and legal fees.
His net worth is largely tied up in his brand name, assets and real estate, but he is estimated to have roughly $425m in cash and liquid assets. If he doesn’t exhaust whatever cash he has to pay the latest penalties against him, his legal jeopardy could make it difficult to find a company willing to secure his bond to appeal it. He could be forced to get rid of his other assets, stripping the Trump name from his properties and airplanes.
An appeal could take months, or years, to get through, potentially overlapping with his second term in the White House, if elected.
The judgments against him aren’t lethal to his company, but he could soon watch his fortunes begin to dissolve, without his family members at the helm, as he visits courtrooms across the east coast for trials connected to his attempts to bury compromising stories of his affair with an adult film star, his possession of classified documents, and his attempts to overturn the results of the 2020 election.
Last year, Judge Engoron accused Mr Trump’s attorneys of elevating “fantasy world” arguments. In Friday’s ruling, he admonished the former president’s apparent inability to admit he has ever done anything wrong, and wouldn’t do anything differently. Mr Trump and his co-defendants’ “complete lack of contrition and remorse borders on pathological,” he wrote.
The chain of events has underscored his reliance on his growing legal battles for his own campaign for the presidency, using his criminal charges and the New York case to paint himself as a victim of political persecution, while telling his supporters that what he claims is a conspiracy against him will come for them, too, unless he stops them.
But Friday’s verdict is as personal as it gets, dealing a legal and reputational blow that threatens to collapse the business he wants to protect and enrich if elected.
A message from his campaign sent while he was in court on the trial’s final day lamented that he wasn’t still campaigning in Iowa before the state’s caucuses. He claimed Democratic officials want him “silenced”. Minutes later, he spoke from the defence table in New York in an uninterrupted, rapid string of grievances and attacks against the judge and attorney general who sued him.
He owes nothing, according to the former president. In fact, he says the state should be paying him, “for what I’ve gone through.”
Throughout the trial, he specifically, publicly railed against the court’s undermining valuations of his Mar-a-Lago resort, his prized refuge. After Friday’s ruling, he fumed in front of cameras from outside its gate.
