Former President Donald Trump suffered a bruising two days in courts this week, with legal setbacks and mounting lawsuits that increasingly threaten his fortune and political future.
Mr. Trump is facing legal turmoil like no other former president in history, and his team’s strategy of fighting to delay investigations flopped with judges in two courts. Sandwiched between those two events was a civil lawsuit filed against Mr. Trump by New York Attorney General Letitia James, a Democrat, seeking $250 million in what she says are ill-gotten gains. She is also seeking to bar the former president from doing business in New York, where he forged his empire.
“When you have multiple appellate judges reject your arguments soundly, a civil case in New York targeting the president and his sons, it is a dark day, and Trump’s legal team is really going to have to reflect on what their next step is,” said Jared Carter, who teaches appellate law at Vermont Law and Graduate School. “The inevitability of the laws and the courts catching up to them is the reality they are facing.”
On Tuesday, U.S. District Judge Raymond Dearie, the special master tasked with reviewing the materials that the FBI seized from Mr. Trump’s Mar-a-Lago estate, mocked the former president’s legal arguments. Judge Dearie repeatedly demanded that his attorneys back up their claims that Mr. Trump had declassified the highly sensitive materials found at his residence.
Growing increasingly frustrated with Mr. Trump’s legal team’s resistance to his request, Judge Dearie accused them of wanting to “have their cake and eat it.”
The next day, Ms. James announced her lawsuit charging that Mr. Trump built his real estate empire by deceiving lenders, insurers and tax authorities to secure more favorable loans, reduce his insurance premiums and pay lower taxes.
Mr. Trump dismissed the lawsuit as a “witch hunt,” but the case seriously threatens the Trump Organization’s ability to obtain loans and do business in New York.
Hours later, a federal appeals court handed the Justice Department a significant victory by restoring access to the classified documents seized from Mr. Trump’s Mar-a-Lago residence as part of its criminal investigation into whether he mishandled sensitive government materials. A lower-court judge had blocked prosecutors’ access to the documents until the completion of Judge Dearie’s review.
The opinion, an astounding rebuke of Mr. Trump’s arguments, was authored by a three-judge panel that included two judges appointed by Mr. Trump.
The darkening legal storm may force the Trump team to shift its strategy, but legal analysts say there are few alternatives. Mr. Trump’s attorneys have tried to delay the process by pursuing the appointment of the special master, whose two-month deadline to complete the review would hold up any indictment.
They also have sought to obfuscate by coyly hinting that Mr. Trump may have declassified sensitive documents, but they stopped short of asserting that the materials have been declassified. In an interview with Fox News host Sean Hannity that aired Wednesday, the former president said he could declassify documents “even by thinking about it” without any formal process.
“Tactically, Trump is trying to string this out, but the way these legal proceedings have developed really show that Trump doesn’t have a strong hand,” said Ilya Shapiro, a senior fellow at the Manhattan Institute. “In terms of an end goal, I don’t know what he’s trying to achieve. He keeps escalating this at every turn, but earlier on if he just returned the documents, it wouldn’t have reached the point of having the raid.”
Legal observers say Mr. Trump would be better served by having an overarching legal strategy aimed at fending off all of his legal headaches. Other legal problems include a federal probe into Mr. Trump’s efforts to overturn the results of the 2020 election and his actions in the run-up to supporters’ Jan. 6, 2021, attack on the U.S. Capitol. A grand jury in Atlanta is focused on efforts by Mr. Trump and his allies to reverse his loss in Georgia.
There is no sign of a resolution to any of these cases soon. Even if Mr. Trump steps away from politics, an unlikely move for someone who loves the spotlight as much as he does, the investigations have gone too deep to be dialed back.
Each case poses a unique risk to Mr. Trump’s fortunes. The New York lawsuit is perhaps the biggest threat to the Trump Organization and Mr. Trump’s personal empire, the classified materials probe could have the most significant criminal implications, and the Georgia probe could do the most damage to the former president’s political brand.
“It was a bad week, but there might be more bad weeks and more investigations to come,” said Carl Tobias, a professor at the University of Richmond School of Law. “Their response to all of this is ad hoc, they are reacting to things instead of anticipating them. When you have a lot of legal issues like this, you need to have a broader strategy that makes it easier to tell a consistent story and think these things through.”
While the risks are adding up, it’s not clear how the legal cases will affect Mr. Trump’s bank account. A campaign finance report for his Save America political action committee revealed that Mr. Trump spent more than $3.8 million in legal consulting fees in August after the FBI searched his residence. The bulk of those legal payments are going to lawyers representing him in the Mar-a-Lago case, but the PAC also made payments to attorneys in other legal cases involving Mr. Trump, including the Georgia probe.
The biggest question this week is whether Mr. Trump’s legal jeopardy will cost him politically.
A New York Times/Siena College poll released Thursday showed that the number of investigations doesn’t appear to have dented the public’s view of Mr. Trump.
Overall, 44% of voters view Mr. Trump favorably and 54% view him unfavorably, according to the poll, which was taken after the Mar-a-Lago raid but before Ms. James’ lawsuit. That was roughly the same level of support for Mr. Trump as in July, when the House committee investigating the events of Jan. 6 held prime-time televised hearings.
The poll also found that 51% of voters thought Mr. Trump had committed serious federal crimes, compared with 38% of voters who thought he had not.
Some of the impact has been mitigated by Mr. Trump’s ability to depict himself as a victim of liberal persecution.
Mr. Trump showcased his iron grip over his loyal supporters last weekend at a “Save America” rally in Youngstown, Ohio, where he received the savior treatment from the thousands who made the pilgrimage. The crowd of people, some who had driven hours to see him, was littered with Trump 2024 T-shirts and hats.
Although Ms. James repeatedly insisted that her lawsuit was not politically motivated, she gave Mr. Trump a line of attack by publicly campaigning for her job on a pledge to investigate the former president.
“I don’t think the investigation will impact the hard-core Trump supporters because it feeds the narrative that the Justice Department has been weaponized for political purposes. But I think with the majority of voters you need to win an election, their view will depend on the outcome of these cases,” said Dave Carney, a Republican strategist based in New Hampshire.
Mr. Carney said he hasn’t seen a single poll in which Mr. Trump’s legal issues have affected voters. He accused Democrats of focusing on the cases against the former president to distract from decades-high inflation and spiraling crime rates.
Democratic strategist Antjuan Seawright agreed that the mounting investigations won’t sway Mr. Trump’s supporters, but he cautioned Democrats not to make their campaigns about the former president.
“Democrats can’t afford to get distracted and make this a conversation about Trump when we’ve accomplished so much since Biden took office,” he said.
• Seth McLaughlin contributed to this report.
• Jeff Mordock can be reached at email@example.com.
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