Donald Trump's Legal Troubles: A Guide
Donald Trump is no stranger to legal trouble, but it’s never been anything he couldn’t solve with his checkbook. Just after he won the White House, Trump agreed to pay $25 million to settle charges that Trump University swindled thousands of students. He later paid another $2 million for misusing his charitable foundation, which was shuttered after authorities documented a “shocking pattern of illegality” and “repeated and willful self-dealing.”
But Trump isn’t going to be able to buy his way out of criminal charges, which he could soon be facing now that he’s the subject of an array of serious criminal investigations — including over shady business dealings and real-estate tax arrangements, as well as his incitement of the January 6th siege of the Capitol. (Trump has made light of the probes against him, writing: “There is nothing more corrupt than an investigation that is in desperate search of a crime.”)
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Trump also faces myriad civil actions, ranging from allegations he violated the Voting Rights Act and the Ku Klux Klan Act (which prohibits the intimidation of public officials), to multiple claims that he defrauded people, including a family member, an investor that bought into his troubled hotel ventures, and “economically marginalized people” looking to “pursue the American Dream.”
The prosecution of a former president would be unprecedented, and the notion that Trump could face dire consequences is hard to fathom given his ability to elude them. As president, he was shielded from prosecution; this is no longer the case. “This is a significant concern for him because he’s no longer in office,” says Rebecca Roiphe, an NYU law professor and former assistant DA in Manhattan. “If he committed a crime like anyone else, I don’t exactly understand how he could escape it.”
Trump will still be able to cry “witch hunt” as the investigations continue to develop, leading some to believe his legal trouble could actually help him should he decide to run again in 2024. And in case you’re wondering, a federal conviction would not disqualify him from doing so.
Below, we cover the waterfront of Trump’s legal troubles:
Manhattan District Attorney
Manhattan DA Cyrus Vance battled all the way to the Supreme Court to obtain eight years worth of Trump’s tax returns and other records — reportedly comprising millions of pages of documents. Vance now has a team poring over these records, and the two-year investigation that began over hush-money payments to Stormy Daniels and Karen McDougal ahead of the 2016 election now appears to include potential bank and insurance fraud, as well as other potential financial crimes.
In May, a grand jury convened to hear evidence from prosecutors, a signal that the investigation could be entering its final stages. The DA’s office is reportedly zeroing in on longtime Trump Organization CFO Allen Weisselberg, probing whether he failed to pay taxes on fringe benefits he received from Trump — including cars, apartments, and private school tuition for his grandchild. The DA’s office has reportedly seized Weisselberg’s personal financial records, and he could be facing charges as soon as this summer, according to The New York Times.
Prosecutors are also investigating whether Trump Organization COO Matthew Calamari enjoyed similar tax-free benefits, indicating the alleged illicit activity could be a company-wide issue. (Neither Weisselberg nor Calamari have commented on the probes or been formally accused of wrongdoing.)
In late June, the Times reported that the DA’s office informed Trump’s lawyers that the entire Trump Organization could be charged in connection with the fringe benefits allegedly provided to Weisselberg. “If this is the way the entire organization is run, then I think we’re getting into the realm where it’s far more dangerous for Trump himself,” says Roiphe, the former assistant DA. “As long as it’s rogue actors and he can push it off on them, then he’s fine. The more pervasive it is and the more people who have high-level responsibility are included, the more likely it is that he’s in some way involved.”
The question now is whether Weisselberg, Calamari, or anyone else the DA’s office may be probing will flip on Trump. Weisselberg has so far refused to do so, but that could change if he’s indicted. “It’s one thing to be loyal to somebody, up until the point where you’re doing jail time for them,” says Roiphe. “It’s quite another when you’re facing that reality.”
New York Attorney General
The state of New York began investigating a civil fraud case against the Trump Organization for its real estate business practices in 2019. But in May of this year, the office of Attorney General Letitia James announced a serious evolution: “We have informed the Trump Organization that our investigation into the company is no longer purely civil in nature,” said spokesperson Fabien Levy. “We are now actively investigating the Trump Organization in a criminal capacity, along with the Manhattan DA.”
Collaboration between the two offices is unusual, but it makes sense considering the overlap in their probes. According to The New York Times, two assistant AGs from James’ office have joined the DA’s team, and James’ office is not conducting its own independent criminal investigation.
In addition to the Weisselberg issues, James has reportedly been investigating potential financial fraud relating to several Trump Organization properties, including the Seven Springs estate in Westchester County, New York. Trump bought the estate for $7.5 million in 1995, failed to turn it into a golf resort, and later claimed a $21 million tax break for conserving its grounds as open space. Trump is infamous for inflating the paper value of his assets, and he reportedly secured an appraisal that valued the full estate in excess of $56 million. Local authorities, by contrast, believed the entire property, Tudor-style mansion and all, was worth only $20 million, less than the deduction Trump claimed for the protected land.
James’ office is also said to be scrutinizing the Trump Tower in Chicago. One of Trump’s lenders reportedly forgave a debt of $100 million on the property in 2012, and authorities are looking into whether Trump paid the necessary taxes on the debt forgiveness. The finances of Trump Organization properties in Los Angeles (Trump National Golf Club) and New York City (40 Wall Street) also appear under the AG’s microscope.
It may seem like Trump is a sitting duck, but Roiphe, the former assistant DA, stresses the difficulties prosecutors will face. “There are a lot of these sorts of crimes that go unpunished,” she says. “There are times when you can be convinced 100 percent as a prosecutor that a crime has been committed, you can know who committed that crime, and you are incapable of bringing that case. It’s frustrating, but it’s the way it works.”
The greatest challenge is not demonstrating wrongdoing, but criminal intent. “It is extremely hard and extremely resource intensive to prove,” Roiphe adds. “There is still a chance that even if he did all of this, and orchestrated a company that was corrupt through and through, he might get away with it.”
In his crusade to overturn the results of the 2020 election and promote the Big Lie that Joe Biden’s victory was illegitimate, Trump turned up the pressure on Georgia election authorities. Fulton County DA Fani Willis is now investigating whether Trump pressuring Secretary of State Brad Raffensperger on a recorded phone call to “find” sufficient Trump votes to overturn the election violated state law, specifically: election fraud conspiracy, criminal solicitation of election fraud, and/or interference with elections duties.
Read letters sent by the DA announcing the investigation.
Voting rights activists in Michigan, joined by the NAACP, are suing Trump for conduct alleged to violate the Voting Rights Act. Trump’s Big Lie pressure campaign included lobbying Wayne County Republican officials against certifying the election totals for the jurisdiction that includes Detroit. The Voting Rights Act forbids the intimidation of voting officials. “[B]y exerting pressure on state and local officials,” the complaint reads, “defendants attempted to and did intimidate and or coerce state and local officials from aiding Plaintiffs and other residents of Detroit, Milwaukee, and other major cities with large Black populations from having their votes ‘counted properly and included in the appropriate totals of votes cast.’”
The suit seeks a declaration that Trump violated the Voting Rights Act and a restraining order forcing the former president to obtain court approval “prior to engaging in any activities related to recounts, certifications, or similar post-election activities.”
Read the complaint.
JANUARY 6th INCITEMENT
Washington, D.C., Attorney General (criminal)
The Attorney General for the District of Columbia announced a criminal investigation into the 45th president’s activities on January 6th, and is reportedly looking at bringing charges against Trump under a local statute that makes it “unlawful for a person to incite or provoke violence where there is a likelihood that such violence will ensue.” The charge reportedly carries a sentence of up to six months in jail.
U.S. Capitol Officers (civil)
Two Capitol police officers who were beaten, maced, poked with flag poles, and pinned against the doors of the Capitol have filed a civil suit against Trump for inciting the violence they endured. “As the leader of this violent mob,” their complaint reads, “Trump was in a position of extraordinary influence over his followers, who committed assault and battery“ on the officers. Conspiracy claims added to the suit allege Trump was in cahoots with the Proud Boys and the Oath Keepers, violent groups whose members stormed the Capitol. “Defendant Trump conspired with the Proud Boys and others to, among other things, incite an unlawful riot on January 6 with the goal of disrupting congressional certification of President Biden’s electoral victory,” it reads. The suit seeks compensatory and punitive damages.
Read the complaint.
Members of Congress (civil)
Rep. Bennie Thompson (D-Miss.) and the NAACP have filed a civil suit alleging a “violation of the Ku Klux Klan Act” — passed during Reconstruction after the Civil War to beat back violent white supremacists in the South — which forbids conspiracies “to prevent, by force, intimidation, or threat” U.S. officeholders from discharging their duties or forcing them to leave the location where those duties must be performed. Thompson and the NAACP claim that “Defendants Trump, Giulini, Proud Boys and Oath Keepers plotted, coordinated and executed a common plan to prevent Congress from discharging its official duties in certifying the results of the presidential election.” The suit seeks a declaration that Trump violated the KKK Act and an order enjoining him from future violations.
Read the complaint.
Former presidential candidate Rep. Eric Swalwell (D-Calif.) has also sued Trump for inciting the insurrection. “Trump directly incited the violence at the Capitol that followed and then watched approvingly as the building was overrun,” the complaint reads. (Swalwell also names as defendants Donald Trump Jr., Rudy Giuliani, and GOP colleague Rep. Mo Brooks of Alabama, who spoke at the rally and whom Swalwell alleges “directly incited the violence at the Capitol that followed.”)
Read the complaint.
SEX AND LIES
E. Jean Carroll (civil)
In 2019, E. Jean Carroll wrote a book claiming Trump sexually assaulted her in the mid-90s in a Bergdorf Goodman department store dressing room. Trump brushed off the accusation, claiming Carroll was “totally lying,” that he didn’t know her, and that the advice columnist and magazine journalist was “not my type.” Carroll sued for defamation. Trump got the Justice Department to stand in as his legal representation, arguing the allegedly defamatory conduct was committed as part of his official duties. Last October, a federal judge ruled the DOJ shouldn’t be standing in for Trump, writing that the president wasn’t a protected “employee” of the government under the statutes in question and that, “Even if he were such an ‘employee,’ President Trump’s allegedly defamatory statements concerning Ms. Carroll would not have been within the scope of his employment.” But the Trump DOJ took the case to federal appeals court. The Biden DOJ is now defending Trump’s claim that the alleged defamation was part of the president’s official conduct.
Carroll’s lawyer Robbie Kaplan tweeted: “The DOJ’s position is not only legally wrong, it is morally wrong since it would give federal officials free license to cover up private sexual misconduct by publicly brutalizing any woman who has the courage to come forward. Calling a woman you sexually assaulted a ‘liar,’ a ‘slut,’ or ‘not my type’ — as Donald Trump did here — is NOT the official act of an American president.” The suit seeks to force Trump “to retract any and all defamatory statements” as well as to pay compensatory and punitive damages.
Read the complaint.
Summer Zervos (civil)
Summer Zervos, a former contestant on The Apprentice, filed a suit alleging Trump defamed her in 2016 when he called her a liar after she accused him of sexual assault in 2007. Zervos was one of several women who publicly accused Trump of sexually predatory behavior prior to the 2016 election, claiming that he kissed and groped her without her consent on multiple occasions. Trump called her story “phony,” prompting the lawsuit. “Donald Trump lied again, and again, and again, and again,” the complaint reads. “In doing so, he used his national and international bully pulpit to make false factual statements to denigrate and verbally attack Ms. Zervos and the other women.”
Trump tried to block the suit, arguing that as president he was immune from legal action. The suit was hung up in the courts for the remainder of Trump’s time in office, but this March the New York State Court of Appeals ruled that it could proceed. The decision could result in Trump being forced to testify under oath. “Now as a private citizen, the defendant has no further excuse to delay justice from Ms. Zervos and we are eager to get back to the trial court and prove her claims,” said Zervos lawyer Beth Wilkinson, according to the Times.
Read the complaint.
FAMILY FORTUNE FIGHT (civil)
Mary Trump, the former president’s niece and author of a tell-all book about her uncle, was an heir to the family fortune when patriarch Fred Trump died. After The New York Times’ 2018 expose about the trajectory of Donald Trump’s fortune and how he routinely manipulated the price of his assets, Mary realized she’d been bought out of her share of the Trump fortune unfavorably. She sued Donald and others in the family, alleging they’d carried out “a complex scheme to siphon funds away from her interests, conceal their grift, and deceive her about the true value of what she had inherited.” Mary, the daughter of Donald’s brother Fred Jr., accused Donald and her other relatives of having “willfully, egregiously, and repeatedly abused their position of trust” to rob her “in order to maximize their own profits.” The suit seeks compensatory and punitive damages.
Read the complaint.
PROFITING FROM HIS OWN INAUGURATION (civil)
The Attorney General of D.C. has sued Trump over diverting 2017 inauguration funds to Trump properties, alleging that the nonprofit inaugural committee “wasted approximately $1 million of charitable funds in overpayment” to Trump businesses that charged exorbitant rates, including $175,000 for a ballroom that usually rented for $5,000. The AG alleges “the Trump Entities … unconscionably benefited from nonprofit funds required to be used for the public good.” The suit seeks to have the ill-gotten gains from the Trump properties donated to public-serving nonprofits.
Read the complaint.
MULTI-LEVEL MARKETING (civil)
In 2018, the Trump family was hit with a class-action lawsuit from a group of anonymous Americans who claimed they were duped by Trump into joining a multi-level marketing scheme — run by a third party called ACN — which Trump was secretly paid to promote. (ACN, itself, is not being sued in this litigation.) The lawsuit alleges that Trump, his company, and his offspring executives Ivanka, Eric, and Don Jr. “operated a large and complex enterprise with a singular goal: to enrich themselves by systematically defrauding economically marginalized people looking to invest in their educations, start their own small businesses, and pursue the American Dream.” The suit asks for class-action status, which would allow others to join the litigation, and for “actual, compensatory, statutory [and] consequential damages.” It also seeks the “disgorgement of all ill gotten gains” by the Trumps.
Read the complaint.
HOTEL DEALS GONE BAD (civil)
The Trump Organization managed a 70-story, sail-shaped high-rise hotel and condo complex in Panama City from 2011 to 2018. In 2019, the investment group Ithaca Capital Partners filed a suit alleging it was fraudulently induced to buy a majority stake in the business by Trump, who’d warranted that the luxury complex was well maintained and successful as a business. In fact, the suit alleges, the Trump Organization was “grossly mismanaging its operations of the former Trump International Hotel & Tower Panama including causing intentional damage to the Hotel Amenities Units and failing to pay income taxes to the Panamanian government.” The suit seeks “not less than” $17 million in damages plus attorney fees.
Read the complaint.
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