Donald Trump’s ability to wriggle out of trouble is so well known that it’s basically become a meme. But over the next few weeks, the former president will face his most difficult legal test yet.
Trump is set to testify this month under oath in two separate court cases, each of which could destroy his family company. He may even face a third deposition in a case that accuses him of abusing the power of the presidency by misusing the Justice Department to punish his former lawyer.
In the weeks between these two precarious depositions, the Trump Organization is also scheduled to appear in a civil trial for beating up protesters on Manhattan’s Fifth Avenue. Meanwhile, criminal charges for dodging taxes are hanging over Trump, and his longtime money man—ex-chief financial officer Allen Weisselberg—could be on trial for dodging taxes, too.
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On top of all that, two law enforcement investigations in Georgia and New York are heating up, targeting Trump’s associates and business partners just as the Jan. 6 Committee lays the groundwork for a criminal referral to the Justice Department for crimes that could disqualify him from running for president again in 2024.
“I don’t suspect that he’s going to have the free time he has had in the past to play any 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 the office of New York Attorney General Letitia James. Trump, Don Jr. and Ivanka will be asked about the roles they had in personally overseeing the way the family company vastly inflated the monetary value of its properties to land inappropriate bank loans and minimize tax payments.
The New York AG’s lawyers have been aggressively pursuing the final stages of their investigation into the way the Trump Organization overstated the size and value of buildings to more easily obtain funding and maximize a tax write-off by amplifying the value of a forested estate that was repurposed as a nature conservation area.
Then, the very next week, the Trump Organization faces trial for the way Trump appears to have directed his security guards to attack protesters who were calling him out for his infamously racist rant about Mexicans when he launched his presidential run in 2015. His deposition in that relatively minor case proved to be a treasure trove of embarrassing details over the way Trump is deathly afraid of getting hit with a pie to the face, his anxiety over flying fruit, and his awkward insistence that he personally oversaw the compensation of an executive whose corporate benefits have come under criminal scrutiny.
At the start of August, attorneys representing angry investors will grill Don Jr., Ivanka, and Eric Trump in a case seeking to prove that the family knew a crappy business phone was a dud but still hawked it as a business opportunity on their Celebrity Apprentice television show. The former president is the final deposition scheduled in the case, which will drag him into a closed-door interview on Aug. 31.
New York lawyer Roberta Kaplan’s team, having recently obtained access to never-before-seen show outtakes that could prove damning, is expected to question the former president in an interview that could paint him as a grifter.
But the end of August also marks the end of a pivotal stage in the ongoing grand jury proceedings going on in Atlanta, where the local prosecutor is building a case that then-President Trump broke state laws when he tried to overturn the 2020 election results there. (Trump was caught on a recorded phone call supposedly trying to intimidate the state’s top election official by instructing him to “find 11,780 votes” to steal Georgia’s 16 electoral votes from Joe Biden.)
Fulton County District Attorney Fani Willis has at least eight subpoenas to Trump lieutenants who were, as her investigators put it, “involved in the multi-state, coordinated efforts to influence the results of the November 2020 election,” a hint that prosecutors may be looking at a mob-like criminal conspiracy case against Team Trump.
The subpoenas also target Trump lawyers who took part in that call to Secretary of State Brad Raffensperger. By Aug. 31, grand jurors at these secretive judicial proceedings are expected to hear the testimony of these eight people in Trump’s orbit—and could play a key role in whether they decide to criminally indict the former president.
The investigation out of Atlanta is where Trump could face the most peril, said former Manhattan prosecutor Adam S. Kauffman.
“The Georgia grand jury is a real threat to him,” he told The Daily Beast. “It’s hard to dispute the conduct. The conduct is on tape. ‘Go find me 11,000 votes and I’ll take care of the rest.’”
As the summer moves into its final weeks, the Select Committee to Investigate the January 6th Attack on the United States Capitol will likely wrap up its televised hearings closely examining Trump’s role in sparking the insurrection—and knowingly allowing armed protesters to march on Congress seeking to kill the vice president.
The committee’s vice chairwoman, Rep. Liz Cheney (R-WY), has already signaled that the nine-person panel could formally ask the Justice Department to pursue criminal charges against Trump—a historic case that could tarnish his aspirations for a political comeback and even bar him from running for office again.
As she told ABC’s This Week in an interview last Sunday, “What kind of man knows that a mob is armed and sends the mob to attack the Capitol and further incites that mob when his own vice president is under threat? When the Congress is under threat? It’s just—it’s very chilling.”
Of course, it’s entirely possible “ol’ Donny Trump” gets out of all these jams once again. Trump has an incredible record when it comes to avoiding legal and political culpability. He has managed to avoid getting prosecuted for obstruction of justice by the DOJ Special Counsel Robert Mueller. He was never charged with election fraud for spending 2016 election funds as hush money payments to a porn star and a former Playboy playmate. And both impeachments by the House of Representatives ended without convictions in the Senate. He has well earned the nickname “The Teflon Don.”
But the convergence of so many cases against Trump during the next few weeks means any one of these issues could become a real problem for the former president. And just when things couldn’t seem to get any worse, the Manhattan District Attorney’s Office is expected to take the Trump Organization and its former CFO to trial for dodging city, state, and federal taxes by coming up with a payment scheme that included off-the-books luxury apartments, a flashy car, and tuition at an exclusive school for his grandkids.
All of these perks weren’t reflected as income, investigators allege, so both the company and the executive were able to avoid taxes.
At the moment, there are signs that Manhattan prosecutors are indeed preparing to bring their case to a conclusion. Jennifer Weisselberg, a key witness in the case who was once married to the former CFO’s son, has been called in by the DA’s office to go over documents and prepare her to testify at trial.
“Things seem to be wrapping up,” said her attorney, Duncan Levin, who previously investigated money laundering at the same DA’s office.
“They’re looking for somebody who can illustrate these documents for the jury and breathe some life into [them],” he said. “She was intricately involved in these issues: What was it like to renovate the apartment? Who paid the bills? Tuition payments to the school… who signed the check?”
Need a hint? It was Donald Trump.
