Teflon Don? What is Trump being investigated for and will anything stick?

When FBI agents descended on Donald Trump’s private Florida club and home Mar-a-Lago on August 8, the former president was huddled with his lawyers in New York, watching the raid unfold through CCTV cameras.

Some agents were dressed casually, in polo shirts and khakis, to blend in at the sprawling seaside estate as they carried out 20 boxes of documents, including 11 marked classified – sensitive material they say Trump should never have taken from the White House. That includes information about foreign leaders but also, reportedly, nuclear weapons – some of America’s most closely guarded secrets.

Trump and his backers have lashed the raid as a “witchhunt”, even drawing comparisons to the Nazi Gestapo police as they try to whip up their base. But legal experts say Trump may be in more hot water than he realises.

Even in the shadow of the Watergate wiretapping scandal that brought down president Richard Nixon in the 1970s, Trump’s legal woes are extraordinary. “Trump makes Nixon look like a boy scout,” says national security law expert and former Justice Department official Professor Alan Rozenshtein.

Since Trump took office in 2016, he’s been under near constant investigation, including two impeachments and allegations his election campaign colluded with Russia. Now, along with the documents furore, he faces investigations into his company finances, his personal finances, a defamation suit brought by writer E. Jean Carroll after he denied raping her in the ’90s – and, of course, most extraordinary of all, allegations he incited the deadly Capitol riot and tried to override legal vote certification to steal President Joe Biden’s victory.

Where are the main investigations at now? How likely are criminal charges? And could any of this disrupt another Trump presidential run?

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What is the Mar-a-Lago raid about?

The battle to retrieve official presidential documents and other sensitive material from Trump has been raging since he left office. By law, they belong to the American people. Yet, as president, Trump had a reputation for destroying or holding on to records he shouldn’t, even flushing papers down White House toilets.

For more than a year, the National Archives and Records Administration had been chasing documents taken to Mar-a-Lago in the chaotic final days of Trump’s presidency, including correspondence with foreign leaders such as North Korean dictator Kim Jong-un. In early 2022, his team did hand over 15 boxes, which they said held all the missing documents. But when officials sifted through them, they suspected some were still unaccounted for – others were marked classified or even “torn up”.

The third potential charge has even bigger implications: a possible violation of the Espionage Act.

In the FBI’s search warrant, since unsealed by the Department of Justice (DoJ), obstruction of justice and mishandling of government records were listed as crimes being investigated by authorities. Those are serious enough, but the third potential charge has even bigger implications: a possible violation of the Espionage Act, a World War I-era law that criminalises any unauthorised retention or disclosure of information related to national defence that could harm the US or aid a foreign adversary. Among the inventory seized was information about the president of France and, according to The Washington Post, documents related to nuclear weapons.

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Fears that Trump may pose a national security risk, as a disgruntled former president, are not new. And Mar-a-Lago has long been viewed as a “security nightmare”, often used by Trump while in office to hold court with world leaders as an unofficial “winter White House”. Though it is secured by the Secret Service, Mar-a-Lago also functions as a country club for unvetted guests, and there have been high-profile breaches. That includes a Chinese national who initially breezed into the estate in 2019 carrying phones and other electronics, saying she was headed to the pool; and when guests observed (and live-tweeted) Trump holding sensitive intelligence talks on the club’s patio with then Japanese prime minister Shinzo Abe in 2017.

Given the FBI needed to show probable cause that a crime had been committed to get its warrant, many experts have suggested that the raid indicates the Justice Department is moving closer to criminal charges for Trump. Others say the search may have been just a means of retrieving the documents, an end in itself. But the DoJ has since flagged that an ongoing criminal investigation is underway. Overnight, when a judge ordered the DoJ to redact sections of the affidavit behind the search warrant so it could potentially be unsealed in the public interest, DoJ officials argued that such an unusual move would reveal the “road map” of an investigation still in its “early stages”, exposing sensitive material and witnesses.

Mar-a-Lago means “sea-to-lake” in Spanish, as it extends between the Atlantic Ocean and the former Lake Worth in Palm Beach, Florida.

Mar-a-Lago means “sea-to-lake” in Spanish, as it extends between the Atlantic Ocean and the former Lake Worth in Palm Beach, Florida.Credit:AP

Experts say the initial “politeness” of authorities (meeting with Trump’s team to request and later subpoena the documents before seeking a warrant) may have actually strengthened any upcoming case against him because it suggests that crucial element for prosecutions of this kind: intent. Former federal prosecutor Renato Mariotti has pointed out, “It will be hard for him to claim he didn’t realise that he had classified government records. It looks like [there would be] a strong case against Trump.”

“The DoJ does not execute search warrants just for fun.”

Attorney-General Merrick Garland made a rare public statement to defend the FBI against public backlash following the search, saying he had personally authorised the decision, which he did not take lightly. “Upholding the rule of law means applying the law evenly without fear or favour,” said Garland, a former federal court judge. (That same day, police shot and killed an armed man who tried to storm an FBI office in Cincinnati, after apparently posting a “call to arms” on social media.)

“The DoJ does not execute search warrants just for fun,” says Rozenshtein.

Trump insists that he had already declassified everything he took home – sitting presidents have broad power to declassify information – but many experts have countered that such orders still need a paper trail to be legitimate.

Either way, in the warrant, Rozenshtein says, the laws raised apply regardless of classification. The DoJ has said it’s highly classified information at stake “and they don’t put in adverbs for no reason … But it’s not actually a defence for Trump to say, no no, I declassified the nuclear codes [or whatever it is].”

The Capitol riot lasted hours and forced lawmakers to hide before the vote certification could continue.Credit:Nine News

What are the inquiries into January 6 and into ‘fake electors’?

Even before the documents raid, speculation was building that charges might be brought against Trump for his role in the deadly January 6 riot, in which his supporters stormed the Capitol to try to stop the 2020 election results (and Biden’s win) being certified.

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More evidence has also emerged, during primetime hearings of a congressional committee investigating, that Trump was part of an elaborate plot to install fake electors in key states – and so overturn the result through a unique quirk of the US electoral college. A criminal probe into the Georgia arm of the plot by district attorney Fani Willis is gathering momentum too, with key figures such as Trump lawyer Rudy Giuliani likely to be charged. Some police injured in the riot are also suing Trump personally.

Rozenshtein says he was once among experts who thought Trump’s First Amendment right to free speech would shield from him any prosecution over the riot (even as some rioters were convicted of seditious conspiracy or other offences). Though Trump is said to have “called up the mob” that day by instructing them to march on the Capitol and again railing against the lawful vote certification underway there, political speech enjoys some of the strongest protections in the US Constitution.

But experts say key elements of intent and conspiracy are beginning to crystallise. Multiple officials and advisers have recounted how they told Trump that investigations had found no election fraud and that Biden’s victory was legitimate, including the country’s then attorney-general Bill Barr. But Trump repeated false claims of a stolen election anyway, even using those lies to fundraise more than $US250 million, according to the congressional committee.

He pressured vice-president Mike Pence to install fake electors and stop the certification, which Pence refused to do and, as the mob that Trump had told to “march on the Capitol” began attacking the building, he watched and did nothing for 187 minutes. Trump aides testified that when they urged him to call off the violence by posting online, he instead tweeted against Pence again. Within moments, rioters were chanting “Hang Mike Pence” as Pence sheltered nearby.

Trump’s speech to supporters before the Capitol riot.

Trump’s speech to supporters before the Capitol riot. Credit:The New York Times

But, for Rozenshtein and many other legal minds, the testimony that “changed the game” and tipped the scales closer to prosecution was the revelation that Trump knew protesters gathering at his rally that day were armed, and even ordered away metal detectors. “They’re not here to hurt me,” Trump said, according to the testimony, under oath, of former White House aide Cassidy Hutchinson. “Let my people in. They can march to the Capitol from here.” Trump himself fought with the Secret Service to be allowed to join them, lunging for the steering wheel of his presidential car, according to Hutchinson’s testimony.

Experts say the charge of obstructing a government proceeding (in this case, the vote count) seems the most likely of those now being whispered about in the halls of power, though Trump could also be charged with defrauding the United States, seditious conspiracy, incitement to riot and insurrection itself. Some would be easier to prosecute than others.

“Was it a conspiracy just to be a jerk or was it conspiracy to commit sedition?”

It would be hard to demonstrate clear links between Trump’s team and rioters in a “seditious conspiracy”, for example, although questions are being asked as to why some rioters seemed to know beforehand that Trump would “spontaneously” call people to march on the Capitol. Still, Rozenshtein says the conspiracy could have been among Trump’s team itself – but “was it a conspiracy just to be a jerk or was it conspiracy to commit sedition?”

Fraud on the government too, would be plausible, he says, but limited by previously narrow Supreme Court interpretations of how it applies to politics. “What does that mean for this case? For the president, no one has any idea.”

Insurrection would be a very appropriate charge “given the gravity of the situation,” he adds. But that civil-war era statue has barely been used. Trump actually has already been impeached (charged by Congress) for inciting insurrection shortly after the Capitol riot, although Republicans blocked his conviction in the Senate.

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As for the Georgia criminal investigation, Trump has hired Drew Findling, known as #BillionDollarLawyer for his history of representing rappers, and Giuliani has been informed he is a criminal target. “And did Rudy Giuliani do something so much worse than what Trump did?” Rozenshtein muses. Remember that now-infamous recording of Trump instructing Georgia’s Republican Secretary of State, Brad Raffensperger, to “find” him enough votes to overturn Biden’s win? “And does Giuliani settle, does he flip?” Rozenshtein wonders. “Georgia is not great for Trump. I gotta say, up until this Mar-a-Lago search warrant, Georgia was Trump’s biggest problem.”

Former president Donald Trump outside Trump Tower on his way to a deposition in a civil investigation by the New York attorney general’s office.

Former president Donald Trump outside Trump Tower on his way to a deposition in a civil investigation by the New York attorney general’s office.Credit:AP

Why are Trump’s taxes and Trump Towers being investigated?

While Trump was raging about the Mar-a-Lago raid and the ongoing January 6 investigations, he chose to keep mum before a New York grand jury. Letitia James, the attorney general there, is probing his company’s affairs in a civil case, including whether the Trump Organisation fraudulently inflated the value of its hotels and other assets by hundreds of millions of dollars.

Trump had fought the deposition for months (and it was then delayed by the death of his first wife, Ivana). When he did finally appear, just two days after the FBI raid, he “plead the Fifth” (invoking his Fifth Amendment right to silence to avoid self-incrimination) some 400 times. His children Ivanka and Donald jnr recently sat for depositions but their brother Eric also plead the Fifth when interviewed in 2020 as part of the inquiry.

If prosecutors win a trial due to begin in October, the company could face hefty fines and restrictions on its operations in New York.

Staying silent was a wise move strategically, Rozenshtein says, given “the criminal exposure is, frankly, scarier than the civil”. It will make launching a criminal case against Trump harder now, he says, for district-attorney Alvin Bragg, who has already been criticised for not yet bringing charges. In February 2021, the Supreme Court ordered Trump to hand over his tax returns and other financial records to prosecutors as part of their inquiry.

And, in a separate criminal case, a top executive at Trump Organisation, Allen Weisselberg, pleaded guilty on Thursday to evading taxes – part of a deal with prosecutors that could make him a star witness against the company. Trump Organisation is accused of helping Weisselberg and other executives avoid taxes on corporate perks such as free apartments and luxury cars. Trump himself is not charged. If prosecutors win a trial due to begin in October, the company could face hefty fines and restrictions on its operations in New York. Bragg said Weisselberg’s plea deal “directly implicates” the Trump Organisation in a “wide range of criminal activity”.

Meanwhile, there are civil investigations into whether Trump’s company profited from his presidency, and a defamation trial brought by E. Jean Carroll against Trump is due to begin early next year.

Former New York Mayor Rudy Giuliani was a key lawyer for Trump during efforts to overturn the 2020 election results.

Former New York Mayor Rudy Giuliani was a key lawyer for Trump during efforts to overturn the 2020 election results.Credit:AP

Why is it so hard to prosecute Trump? Are charges likely?

In office, Trump was protected by an internal rule within the Justice Department not to indict a sitting president. It’s considered untenable for “the nation’s chief law enforcement officer” to face charges from his own department, Rozenshtein explains. “That’s why we have an impeachment process.”

Presidential candidates, meanwhile, can be charged. But the DoJ has another rule: not to take any public steps to disrupt the outcome of an election close to the day. That’s why there was so much controversy over then FBI director James Comey’s decision to announce he was reopening an investigation into Democrat Hillary Clinton’s use of a private email server for official business 11 days out from the 2016 election. (It was closed again just days later without finding any mishandling of classified information.)

Andrew Goldstein, one of the lead investigators who examined whether Trump tried to obstruct the Mueller investigation into Russian collusion in Trump’s 2016 election campaign, told The New York Times that bringing charges won’t be easy. Prosecutors will need to believe the evidence can satisfy the high criminal standards of “beyond reasonable doubt”, and survive appeals. And the DoJ will have to seriously consider whether such charges, against a potential candidate for president, are in the country’s interest.

But they’ll have to look at the ramifications of not prosecuting too, said Goldstein (who ultimately declined to make a decision on prosecuting Trump given Trump was still president at the time). If there was clear, straightforward evidence of a crime “but the Department of Justice walked away, there is a real risk of the American people thinking that there are two systems of justice,” he said. “And that would be devastating.”

“I’m a law professor and…as insane as you think it is, it’s 10 times more insane.”

Still, there’s no precedent. While other countries have prosecuted former leaders, no president (former or sitting) has ever been convicted of a crime in the US, and prosecutors are often wary to be the first to test new legal terrain. “As insane as you think it is, it’s 10 times more insane,” Rozenshtein says of the situation. “The US, the world’s hyper power, is considering for the first time indicting a former president who is [de facto] head of the opposing party, for a crime against democracy. I’m a law professor, paid to sit and think these thoughts, but we’d be kidding ourselves if we think we can know how the statues will apply to a president. I think the last time a [sitting] president was charged with a ‘crime’ was when Ulysses S. Grant was pulled over for speeding in his carriage.” (The misdemeanour case against Grant was dismissed.)

Still, Rozenshtein’s gut feeling is that Trump will be charged with something. “Between Mar-a-Lago and January 6 with the fake elector scheme, there’s just so much there.” The documents case seems the furthest advanced. “I also think that, legally, it’s the most straightforward case. It doesn’t raise any tricky First Amendment issues … and [while Trump was still president during the riot], he was holding on to the documents as a private citizen.”

It would be ironic if the thing that gets him, in the end, are 20 boxes of documents, especially given he used the controversy over the emails of Democratic rival Hillary Clinton to campaign against her. But Rozenshtein is among experts who don’t think that would hold Trump properly to account. As two law professors argue in The Washington Post, “it’s not like prosecuting Al Capone, the notorious gangster who was charged with tax evasion … it is critical for public perception, for history – for the preservation of democracy – that if [Trump] is charged, it is first and foremost with the crimes that best reflect the gravity of the danger he posed to the country.”

Rozenshtein says that gravity could “make it worth taking the risk” with a less tested charge such as insurrection. On the other hand, losing such a high-profile case? “That’s gonna be a mess. There’s a famous phrase: if you strike at the king, you better strike to kill. [Politically] the only thing worse perhaps, than not trying Trump, is trying Trump and him being acquitted … This is why I don’t envy Garland.”

Any such case would likely begin in the District of Columbia, where Washington is, and then find its way up to the Supreme Court. Trump might have stacked its bench with conservative justices (who have recently expanded gun rights and struck down the constitutional right to abortion) but they shot down Trump’s legal campaign to overturn votes in the frantic days after election night so it’s unclear how they would react.

In such complicated cases, Rozenshtein says it takes time for the wheels of justice to turn. Trump hasn’t even been out of office two years. “I think it’s just too early to know if he really is Teflon Don.”

The Trump rally is considered to have ignited the Capitol riot on January 6.

The Trump rally is considered to have ignited the Capitol riot on January 6.Credit:AP

Could Trump be disqualified from another presidency?

Trump is expected to announce another tilt at the top job. But even if he were to be convicted of a federal crime such as insurrection or mishandling official records, it would be unlikely to stop him running.

Here’s why: Although many of the potential charges facing Trump bar people from holding public office if convicted, experts say the Constitution still trumps such statues, and it lists only three qualifications for president: being a US citizen, at least 35 years old, and having lived in the US for 14 years.

“It’s never been a problem,” says Rozenshtein. “Until now.”

There are just two ways to get banned from the Oval Office, he says. If you are impeached and convicted by the Senate, it can also bar you from holding office again. So far, both times that Trump was impeached as president, Republicans blocked his conviction – first in 2019 for abuse of power (by soliciting foreign interference to help him win re-election, as well as trying to obstruct an inquiry into it) and then in 2021 (for inciting insurrection over the January 6 riot).

Lawmakers behind the Capitol riot hearings are looking at ways to shore up the republic against future insurrection and attempted election steals.

But technically, there’s an argument that Trump could be impeached again, though he’s no longer president. Many Republicans voted not to convict Trump in his second impeachment because by the time it came before the Senate he was no longer in office. But Rozenshtein says that’s their interpretation. The question has not been resolved. “Theoretically, I think the house could impeach Trump again, and then the Senate could – if they could get two-thirds – bar him from office. The problem is, you’re not gonna get two-thirds of the Senate to vote yes.”

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Lawmakers behind the Capitol riot hearings, meanwhile, are looking at ways to shore up the republic against future insurrection and attempted election steals and that’s thrown light back on that little-known insurrection statue. Democrat Jamie Raskin, who serves on the committee, has pointed to Section 3 of the 14th Amendment: it stops people, including presidents, who have engaged in insurrection and rebellion after previously swearing an oath to defend the constitution from serving in office again.

But even that would be fraught to enforce, Rozenshtein says. “I don’t think that DoJ is thinking about which charges to pursue, based on disqualifying Trump from running for president.”

Still, Rozenshtein expects the department will clear up the question of charges before the next election arrives (and, potentially, put Trump back under presidential immunity). “This is gonna happen much faster than that.”

Whatever happens, to some extent, he thinks it’s a shame that “the law has to come in and deal with what is fundamentally a political problem”. “At some point, the law just cannot solve that problem for America.”

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