For Trump, Friday’s verdict is not just business. It’s personal.

9 months ago

Donald Trump has faced no shortage of legal peril since leaving office.

But few cases have mattered more to him on a personal level than the civil fraud trial over his business practices in New York, according to those who know the former president. Trump has publicly fumed over the low valuation of his oceanfront Palm Beach club, Mar-a-Lago, and made a point to show up in person to defend himself in court. And few verdicts could affect his carefully cultivated reputation as a businessperson more than the one issued in that trial on Friday, in which the former president was hit with over $350 million in penalties by a judge for falsely inflating his net worth to get more favorable rates from banks and insurers.

“This was a namesake company that he built from the ground up when he was starting his career, and that came to define his life before he even became president and before he even became a television star,” a person close to Trump, who has discussed the case with him, said. “This is what he's always wanted to do. It's the family business. He’s trying to defend all of that.”

The judge also imposed a three year ban on Trump serving any roles in his New York-based company, and put similar two-year bans on his sons, Eric Trump and Donald Trump Jr., both senior executives in the Trump Organization, from running the company and fined them each $4 million.

But the harm from that verdict cannot be measured solely in dollar signs and business transactions.

For decades, Trump has cast himself as a successful businessperson, even as he sometimes struggled to keep his company afloat. From his NBC show, “The Apprentice,” to his series of books on getting rich, cutting deals and thinking “like a billionaire,” Trump marketed himself as the savviest of tycoons to the American masses.

Trump is worth billions, according to estimates from Forbes and Bloomberg, with much of his wealth wrapped up in his New York City real estate portfolio, hotels, golf resorts and clubs. While there’s been endless speculation about the validity of those estimates, experts still believe he will be able to afford the damages and fines, although has pledged to appeal it and is likely to delay any payment until he has exhausted all legal options.

But the verdict itself is a reputational hit, denting the perception that the Trump Organization is anything but a shining success. And it matters on a personal level to Trump, too. Not only does he see this as part of a “witch hunt” that wants to destroy his political future, but he also is invested in handing off a solid company to his children, who now run it.

“He views these judgments as a kind of existential threat to his entire brand,” said Tim O’Brien, a Trump biographer turned critic. “It will wear at him psychologically.”

A Trump ally declined to engage in the psychological effect the verdict might have on him. While they have no doubts Trump — who has worn his aggravation about the case on his sleeve during court appearances — will be angry about the outcome, the person described it as “obviously political” and unlikely to shift public opinion.

“I don’t think this will have any effect on anything moving forward. It will just reinforce the feelings of those who already hate him, and for the people who love him it will reinforce that the system is corrupt and out to get him,” the person said, who spoke on the condition of anonymity, and only addressed the political impact the ruling would have.

The last time Trump found himself facing serious financial losses was in the early 1990s, when his entire real estate empire was at risk of falling apart under over $3 billion in debt.

“It was the most devastating experience of his life. He was going through divorces, everything was falling around him. He became sullen, combative, pouty and I think it was not an era he's ever wanted to revisit, though circumstances creep up on him again because he’s a debt monster and can’t help himself,” O’Brien said, “Judgments like this are scary because they bring back echoes of the early 1990s.”

But Trump, ever the marketer, turned those early '90s setbacks around, recasting himself as a television personality and reestablishing his brand as a business savant.

He then branched out further, entering politics. And, as a politician, he used those marketing skills to turn the legal judgments against him into campaign rallying cries. Trump has claimed that the justice system is rigged and his supporters have, largely, been convinced.

“He’s frustrated for being a target, and he’s frustrated for what it means. This is an escalation we've never gone through in this country, where we weaponize the courts to go to an extreme after somebody,” said Bryan Lanza, who worked on Trump’s 2016 campaign and remains close to his current team.

Even though Trump sees a spike in polling and fundraising after major legal moments, his advisers do not view any of these court cases as entirely helpful. They pull Trump off the campaign trail and distract from their political message.

But, increasingly, Trump’s legal problems and campaign have become one and the same. And as the former president emerged from Friday’s verdict, it was clear that there were personal elements intertwined too.

“I helped New York City during its worst of times,” read part of Trump’s statement, “and now, while it is overrun with Violent Biden Migrant Crime, the Radicals are doing all they can to kick me out.”

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