Summary List Placement
Former President Donald Trump and his advisors are vacillating between deep concern and cavalier confidence over his potential legal exposure and the ever-present possibility he could end up in the history books as the first president of the United States — current or former — ever to be indicted.
The growing list of criminal investigations and civil lawsuits keep piling up, while Trump remains ensconced in his South Florida oceanside compound Mar-a-Lago.
Alongside a rotating cast of attorneys, Trump has warily watched as local Georgia and New York investigators escalate their inquiries connected to both his slapdash efforts to hold on to the presidency despite losing the 2020 election and his namesake company’s finances.
Notably, the ex-president is also hearing from advisors that he faces little legal risk from the January 6 rioting at the Capitol, according to a dozen advisors, legal experts, and Republicans close to the former president.
In interviews, many of the people around Trump described the Georgia and New York investigations as more “politicized” and dangerous than the threat posed by the Justice Department’s examination of a deadly insurrection carried out by a pro-Trump mob.
“If I were Trump, I’d be most concerned about the business activities in New York,” said Alan Dershowitz, the retired Harvard law professor who represented the president during his first Senate impeachment trial in early 2020.
“Because when you have a prosecutor hell-bent to get you, and you’ve had a long career in business, there’s always a possibility they could come up with some technical violation, more likely with his companies than him personally,” Dershowitz added.
Dershowitz echoed a number of Trump advisors who expressed confidence that the former president would not face prosecution from the Justice Department over what transpired when Congress met to certify the 2020 election results on January 6.
They also took a similar view toward civil lawsuits seeking to hold Trump accountable for his statements leading up to the attack on the US Capitol, saying the former president’s rhetoric fell well within the First Amendment’s free-speech protections.
“He should have no concern,” Dershowitz said. “The idea of him being prosecuted for a speech like that would be rejected 9-0 by the Supreme Court. It’s not even a close case.”
Another Trump associate added: “There’s about a 0% chance of criminal liability on the president based on what he said on January 6, and it’s close to the same thing for any civil liability.”
DOJ ‘looking at everything’
One thing is certain: Trump has not shed his legal woes since departing the White House in January. All indications point to his predicament growing ever more dire.
In New York, investigations into the Trump Organization have gathered steam with favorable court rulings cracking open the former president’s tax returns and a subpoena seeking the bank records of the company’s longtime chief financial officer, according to a New York Times report published Wednesday.
In Georgia, a newly elected district attorney is examining whether Trump made efforts to manipulate election results in the state, including with a phone call first reported by The Washington Post in which the president appeared to pressure the Georgia secretary of state to “find 11,780 votes.” Two grand juries are involved in the closed-door proceedings, The Daily Beast reported.
A recording of Trump’s call to Georgia Secretary of State Brad Raffensperger surfaced in January during the early days of Fani Willis’ tenure as the district attorney of Fulton County, Georgia. Since then, she has assembled a team that includes a nationally renowned expert on racketeering charges as she delves into Trump and his inner circle.
In Washington, DC, a Trump-appointed prosecutor recently said in a CBS “60 Minutes” interview that the former president could indeed face legal jeopardy over remarks that were seen as egging on the crowd that went on to overtake the Capitol.
Federal prosecutors have so far brought cases against more than 300 people on charges varying from unlawfully entering the Capitol to assaulting a police officer. Michael Sherwin, the now former US attorney in Washington who oversaw the initial wave of cases against the people charged in the riot, raised the possibility on “60 Minutes” that the former president might be “culpable” and that investigators were “looking at everything.
“It’s unequivocal that Trump was the magnet that brought the people to DC on the 6th,” Sherwin said. “We have soccer moms from Ohio that were arrested saying, ‘Well, I did this because my president said I had to take back our house.’ That moves the needle towards that direction. Maybe the president is culpable for those actions.”
Trump’s ‘walk-on’ legal team
With Trump’s legal troubles only mounting, the former president’s advisors are concerned about his ability to attract high-powered legal talent should the need arise.
Over the course of his four years as president, Trump garnered a reputation as a difficult client who would often resist — or outright ignore — legal advice. He’s also known from his pre-politics life for not paying his attorneys for their services. Not being president anymore isn’t helping either.
“It’s a reality that the traditional rock-star lawyers you would see in a high-stakes matter involving a president or former president … he doesn’t really have access to those people anymore,” a former Trump administration official told Insider.
“For big firms or small firms with big clients, it doesn’t sell well if you’re associating in any way with Trump,” the former official said. “And it’s much more true as a former president. As a president, you could serve Trump and believe that you were working for the country, but now you’re just serving Trump.”
This person added: “He had a hard enough time attracting good lawyers during his presidency. Attracting them now is virtually impossible.”
Trump has indeed cycled through a long list of respected criminal-defense counsel — including John Dowd, Jay Sekulow, Ty Cobb, Pat Cipollone, and Emmet Flood — either in the White House or as outside personal representation during the special counsel Robert Mueller’s investigation into Russian interference in the 2016 election.
Sekulow and Cipollone had starring roles later on defending Trump in early 2020 during what turned out to be the first of two Senate impeachment trials. They worked alongside two top White House lawyers in Patrick Philbin and Michael Purpura, along with Dershowitz, former Florida Attorney General Pam Bondi, Bill Clinton’s nemesis Ken Starr, and Eric Herschmann, a partner at the law firm Kasowitz Benson Torres who would later become an official presidential legal advisor.
Trump’s challenge in retaining lawyers was also on full display during his second Senate impeachment trial earlier this year over his role in the January 6 riot at the Capitol. The entire defense team that represented the president during that first trial in January and February 2020 stayed far away from the counsel table when they were needed again.
Several new lawyers who Trump had lined up also abruptly pulled out of the proceedings just before the trial got started. The Trump team ultimately went on to face widespread ridicule for meeting the House Democratic managers’ emotional presentation with arguments that were considered dry and oftentimes dispirited.
“I wouldn’t even put them on JV,” the former Trump administration official said of the lawyers the president ended up using for his Senate trial, which ended like the first did — with an acquittal. “I think they would be dismissed walk-ons. You just wouldn’t see them on a crack high-stakes legal team.”
In Trump’s small circle since leaving the White House, his former deputy campaign manager Justin Clark has kept his spot as one of the top legal coordinators, according to Trump advisors who spoke with Insider.
Clark was responsible for coordinating Trump’s legal efforts to find evidence of voter fraud and help overturn the 2020 election results. But Trump’s post-election efforts came up empty, and multiple Trump advisors privately pinned the blame on Clark for his handling of legal efforts across battleground states.
In New York, Trump has held on to a defense team of respected lawyers, including Jane Raskin, Marc Mukasey, Alan Futerfas, and Sekulow, who’s argued on Trump’s behalf before the US Supreme Court. Lawrence Rosen, a defense attorney who advised Trump on legal issues tied to a hush-money payment to the adult-film star known as Stormy Daniels, is also helping the former president in the New York attorney general’s investigation.
Sekulow declined to comment, citing his ethical obligations as a lawyer. But within Trump’s orbit, past advisors took note that he Sekulow not involved in the former president’s second impeachment trial after prominently defending him during the first one.
In an interview, the former Trump administration official said Sekulow had been “stiff-arming” the president even as he’s remained in his good graces.
“He didn’t participate in the impeachment. He didn’t do a lot of things I know the president would have preferred to have him in — some things that he skillfully avoided,” the former administration official said.
In the wave of unsuccessful election lawsuits, Sekulow limited his role to challenging the Pennsylvania Supreme Court’s decision to grant three extra days for the receipt of mail-in votes in the November election. The US Supreme Court declined to hear the case, in which Sekulow was seen as advocating a legitimate constitutional question, while stopping short of buying into Trump’s voter-fraud claims.
Sekulow was joined in that case by William Consovoy, a conservative litigator and former clerk for Justice Clarence Thomas who represented Trump in efforts to prevent House Democrats from obtaining his financial records.
Not just a criminal matter
This week, more legal exposure came Trump’s way. On Tuesday, a pair of Capitol Police officers sued the former president over injuries they suffered on January 6. The lawsuit alleged Trump “inflamed, encouraged, incited, directed, and aided and abetted” the insurrectionist mob.
In the weeks since January 6, House Democrats have also brought civil lawsuits accusing Trump, his son Donald Trump Jr., and former New York City Mayor Rudy Giuliani of inciting the deadly insurrection that also stalled for hours the ceremonial congressional certification of the 2020 presidential-election winner.
Trump has turned in those cases to Jesse Binnall, a little-known lawyer in Alexandria, Virginia, who joined in the then-president’s push last year to contest the electoral results in multiple states. Binnall’s case in Nevada was rejected by the state Supreme court, and similar efforts by the Trump campaign failed in courtrooms across the country.
Binnall previously defended former Trump national security advisor Michael Flynn as he sought to pull out of a plea deal in which he twice admitted to lying to investigators about his past communications with the Russian ambassador. The Justice Department eventually moved to drop the case, and Trump pardoned Flynn in the final weeks of his presidency.
In the election fights and the Flynn case, Binnall worked alongside Sidney Powell, a lawyer who joined Giuliani in making baseless claims of election fraud. Powell came under criticism even within Trump’s orbit over her handling of the election litigation, and the then-president himself described her many misspellings in court filings as “very embarrassing.”
Powell is now an outcast as she faces a defamation lawsuit from the election-infrastructure company Dominion Voting Systems over her claims of widespread fraud. In the litigation, she recently said “reasonable people would not accept” her claims of election fraud “as fact but view them only as claims that await testing by the courts through the adversary process.”
Giuliani, at once both Trump’s most influential legal advisor and the cause of many of his headaches, has similarly drifted out of the former president’s orbit since the January 6 attacks, Trump advisors told Insider.
Some Trump advisors said they saw that as a function of Giuliani’s concern for his own possibly extensive legal jeopardy, from his efforts to overturn the 2020 presidential election results to his extensive dealings in Ukraine with his former associates Lev Parnas and Igor Fruman that caught the eye of federal prosecutors who filed campaign-finance charges against the two men in 2019. Parnas and Fruman have both pleaded not guilty, and their trial has been delayed until October over COVID-19 restrictions.
Others close to the president said it was highly unlikely Giuliani had totally fallen out of Trump’s orbit. The two men have known each other for decades, and the former New York mayor is likely just keeping a lower profile than usual.