Former President Donald Trump suffered a bruising two days in the 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 separate courts. Sandwiched between those two events was a stunning civil lawsuit filed against Mr. Trump by Democratic New York Attorney General Letitia James 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 seized by the FBI from Mr. Trump’s Mar-a-Lago estate, mocked the former president’s legal arguments. Judge Dearie repeatedly demanded Mr. Trump’s lawyers back up their claims that the former president 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 unveiled her lawsuit claiming that Mr. Trump’s real estate empire was built on deceiving lenders, insurers, and tax authorities. She alleged Mr. Trump did this to secure more favorable loans, pay lower taxes and reduce his insurance premiums.
Mr. Trump dismissed the lawsuit as a “witch hunt,” but it seriously threatens the Trump Organization’s ability to obtain loans and do business in New York.
Although Ms. James said she couldn’t file criminal charges, she referred evidence to the Justice Department and Internal Revenue Service.
Hours later, a federal appellate court handed the Justice Department a significant victory, 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 Judge Dearie completes his 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. So far, Mr. Trump’s lawyers have sought to delay the process by seeking the appointment of the special master, whose two-month deadline to complete the review would hold up any potential indictment.
They’ve also sought to obfuscate by coyly hinting that Mr. Trump may have declassified sensitive documents, but stopping short of asserting the materials have been declassified. In an interview with Fox News host Sean Hannity that aired Wednesday, the former president claimed he could declassify documents “even by thinking about it,” and that no formal process was needed.
“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 Illya 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 woes 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 the Jan. 6 attack on the U.S. Capitol by his supporters. A grand jury in Atlanta is focused on efforts by Mr. Trump and his allies to reverse President Biden’s election win in Georgia.
There is no sign any of these cases will ease up soon. Even if Mr. Trump were to step away from politics, an unlikely move for someone who loves the spotlight as much as he does, the investigations are too far along to be dialed back at this point.
And each case poses its own 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 has potentially the most significant criminal implications, while the Georgia probe could do the most damage to his 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 unclear how that will impact Mr. Trump’s wallet. A campaign finance report for his “Save America” political action committee revealed Mr. Trump spent over $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 arising this week is whether Mr. Trump’s legal jeopardy will cost him politically.
A New York Times/Siena College poll released Thursday revealed that the number of investigations doesn’t appear to have dented the public’s view of him.
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 primetime hearings.
The poll also found that 51% of voters thought Mr. Trump committed serious federal crimes, compared with 38% of voters who thought he had not.
Some of the probes’ 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 at a “Save America” rally in Youngstown, Ohio, last weekend where he received the savior treatment from the thousands who made the pilgrimage. The crowd was littered with Trump 2024 T-shirts and hats, and was composed of people who had driven hours to see him.
While Ms. James repeatedly insisted 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 where Trump’s legal issues have impacted voters, accusing Democrats of focusing on it to distract from decades-high inflation and spiraling crime rates.
Democratic strategist Antjuan Seawright agreed that Mr. Trump’s supporters won’t be swayed by the mounting investigations. 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 article.