Donald Trump’s Summer of Legal Hell

Donald Trump’s ability to wriggle out of trouble is so prolific that it’s essentially become a meme. But the next few weeks are secretly among the former president’s most legally dangerous.

Trump will testify under oath in two separate trials this month, both of which could destroy his family business. He may even face a third hearing in a case alleging he abused the powers of the presidency by using the Justice Department to punish his former attorney.

In the weeks between those two precarious statements, the Trump Organization is also said to be in a civil trial for beating up protesters on Manhattan’s Fifth Avenue. Meanwhile, Trump faces tax evasion charges, and his longtime financier — ex-CFO Allen Weisselberg — could also face trial for tax evasion.

To make matters worse, two law enforcement investigations are ongoing in Georgia and New York targeting Trump’s associates and business associates, just as the Jan. 6 committee is laying the groundwork for a Jan. 6 criminal referral to the Justice Department for crimes that could bar him from 2024 run again for the presidency.

“I don’t think he’ll have the free time he’s had in the past to play golf,” said Michael Cohen, Trump’s longtime consigliere, who has since turned on his former boss.

During the week of July 18, Trump and two of his adult children will face tough questions from New York Attorney General Letitia James. Trump, Don Jr. and Ivanka are asked about their role in personally overseeing the way the family business grossly inflated the monetary value of its properties to improperly land bank loans and minimize tax payments.

Lawyers for New York AG have been aggressively pursuing the final stages of their investigation into how the Trump Organization overstated the size and value of buildings to more easily obtain financing and maximize a tax write-off by increasing the value of a wooded property increased has been repurposed as a conservation area.

Then, as early as next week, the Trump Organization faces a trial over what appears to be Trump’s ordering of his security forces to attack protesters who called him out about his notorious racist tirade about Mexicans when he launched his 2015 presidential bid. His testimony in this relatively minor case turned out to be a treasure trove of embarrassing details about the way Trump is scared to death of being hit in the face with a cake, his fear of flying fruit and his awkward insistence that he personally receive the compensation of an executive whose corporate benefits were being prosecuted.

In early August, attorneys representing disgruntled investors will spy on Don Jr., Ivanka and Eric Trump in a case designed to prove the family knew a crappy business phone was a dud but still sold it as a business opportunity on their ‘celebrity’ praised apprentice” TV show. The former president is the latest testimony scheduled in the case, which will draw him into a behind-closed-doors interview on August 31.

New York attorney Roberta Kaplan’s team, who recently gained access to never-before-seen show outtakes that could prove scathing, are expected to question the former president in an interview that could frame him as a crook.

But late August also marks the end of a crucial phase in the ongoing grand jury trial in Atlanta, where the local prosecutor is building a case that then-President Trump broke state statutes when he tried to overturn the 2020 election results there. (Trump was caught on a taped phone call allegedly trying to intimidate the state’s top election official by instructing him to “find 11,780 votes” to steal Joe Biden Georgia’s 16 electoral votes.)

Fulton County District Attorney Fani Willis has at least eight subpoenas on Trump lieutenants who, as her investigators put it, “were involved in coordinated efforts by multiple states to influence the results of the November 2020 election,” an indication that prosecutors could be looking at a mob-style criminal conspiracy case against Team Trump.

The subpoenas also target Trump attorneys who participated in that call to Secretary of State Brad Raffensperger. By August 31, the grand jury in this secret trial is expected to hear the testimonies of these eight people in Trump’s orbit — and could play a key role in whether they decide to criminally indict the former president.

Trump may face the most danger in the investigations outside of Atlanta, said former Manhattan District Attorney Adam S. Kauffman.

“The Georgia grand jury is a real threat to him,” he told The Daily Beast. “It’s hard to challenge the behavior. The behavior is on tape. ‘Find me 11,000 votes and I’ll take care of the rest.’”

As summer enters its final weeks, the special committee investigating the Jan. 6 attack on the United States Capitol is likely to conclude its televised hearings, during which it will scrutinize — and deliberately arm — Trump’s role in instigating the insurgency Allowed protesters to march into Congress to do so kills the Vice President.

The committee’s vice chair, Rep. Liz Cheney (R-WY), has already signaled that the nine-member panel could formally ask the Justice Department to file criminal charges against Trump — a historic case that could cloud his aspirations to make a political comeback on him even prevent them from running for office again.

As she said in an interview with ABC’s This Week last Sunday, “What man knows a mob is armed and sends the mob to attack the Capitol and further incites that mob when his own VP is threatened ? When Congress is threatened? It’s just – it’s very frightening.”

Of course, it’s entirely possible that “old Donny Trump” will emerge from all these jams again. Trump has an incredible record at avoiding legal and political guilt. He managed to avoid prosecution for obstruction of justice by Justice Department Special Counsel Robert Mueller. He was never charged with voter fraud for using 2016 election funds as hush money payments to a porn star and former Playboy playmate. And both impeachment trials in the House of Representatives ended without convictions in the Senate. He has honestly earned the nickname “The Teflon Don”.

But the convergence of so many cases against Trump over the next few weeks means any of these issues could become a real problem for the former president. And just when things couldn’t get any worse, the Manhattan Attorney’s Office is expected to take the Trump Organization and its former CFO to court for evading city, state and federal taxes by implementing a payment system that includes an exemption – the-books luxury apartments, a flashy car and lessons at an exclusive school for his grandchildren.

All of those perks weren’t reflected as income, investigators claim, allowing both the company and the executive to avoid taxes.

For now, there are signs that Manhattan prosecutors are indeed preparing to complete their case. Jennifer Weisselberg, a key witness in the case who was once married to the former CFO’s son, was brought in by prosecutors to review the documents and prepare them for her testimony in court.

“Things seem to be coming to an end,” said her attorney Duncan Levin, who previously investigated money laundering at the same prosecutor’s office.

“They are looking for someone who can illustrate these documents for the jury and bring them to life [them],” he said. “She was intensely involved with these questions: What was it like renovating the apartment? Who paid the bills? Tuition to the school … who signed the check?”

Need a hint? It was Donald Trump. Donald Trump’s Summer of Legal Hell


Hung is a Interreviewed U.S. News Reporter based in London. His focus is on U.S. politics and the environment. He has covered climate change extensively, as well as healthcare and crime. Hung joined Interreviewed in 2023 from the Daily Express and previously worked for Chemist and Druggist and the Jewish Chronicle. He is a graduate of Cambridge University. Languages: English. You can get in touch with me by emailing:

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