The Complete Guide to All the Ways Donald Trump Is Legally Screwed

Bess Levin / Vanity Fair
The Complete Guide to All the Ways Donald Trump Is Legally Screwed Donald Trump. (photo: Quinton McMillan/Getty Images/Shutterstock)

Every single criminal investigation and civil lawsuit the ex-president is currently facing, including the ones you’ve probably never heard about.

After Donald Trump’s private residence at his Palm Beach club was raided by the FBI, his defenders immediately jumped to point out how unprecedented it was for the feds to search the home of a former U.S. president. And it’s true—it definitely was unprecedented! Though not because, as Trump’s stooges claimed, the whole thing was some kind of politically motivated witch hunt. Rather, no president in history has been as corrupt as Donald Trump—including the one who was forced to resign in disgrace. Even before the FBI came a-knocking, the 45th president was up to his neck in legal woes; in fact, it’s likely gotten to the point where you can’t even keep track of all the criminal investigations, civil lawsuits, and other reasons Trump’s lawyers should just move into Mar-a-Lago so that they can brief him daily over breakfast re: all the ways he’s f--ked.

Unfortunately, for the rest of the public, it’s not as easy to keep track, and you might find yourself confused between, say, the New York attorney general’s investigation into the Trump Organization and the Manhattan district attorney’s criminal probe, the latter of which is expected to lead to a guilty plea from the company’s longtime CFO, Allen Weisselberg. You might also struggle to keep straight the subjects of the various federal investigations, which range from Trump’s plot to overturn the election to Trump’s decision to take classified government documents to his home.

Which is why, as a public service, we’ve put together this handy-dandy guide.

The Classified-Documents Investigation

Though you presumably don’t need reminding, on August 8, 2022, the FBI executed a search warrant at Trump’s residence at his for-profit Florida club, where they removed 11 boxes of classified documents, including some marked top secret. Trump’s defenders lost their minds over this, insisting that the government should have simply subpoenaed him or just asked him nicely to return what wasn’t his to keep. Of course, that’s exactly what the feds had initially tried to do. Back in January, the National Archives had removed 15 boxes of documents from Mar-a-Lago, which also included those of the top secret variety. Several months later, the Justice Department, believing that Trump hadn’t actually turned over everything he was supposed to, issued a subpoena for the additional documents. In June, a lawyer for the former president said in a written statement that all classified material had been returned to the government. Which, of course, turned out to be a lie, hence the need for the raid.

Then, after a judge unsealed the search warrant, we learned that the government wasn’t looking for West Wing tchotchkes and pilfered office supplies, but rather had probable cause to believe that the 45th president had engaged in obstruction of justice, mishandled government records, and violated the Espionage Act. The night before the warrant was unsealed, The Washington Post reported that “classified documents relating to nuclear weapons were among the items FBI agents sought in a search of former president Donald Trump’s Florida residence.” The New York Times revealed this week that the FBI had interviewed Trump’s White House counsel and deputy counsel concerning the documents. While it’s not clear what will happen next, an indictment is obviously a strong possibility. If found guilty of violating the statutes cited in the warrant, Trump could go to prison for decades.

Naturally, he’s insisted he did nothing wrong and that people take classified documents all the time.

The Justice Department’s Criminal Investigation of January 6 and the Plot to Overturn the Election

With all the hubbub surrounding the raid on Trump’s home and the revelation that he refused to return top secret documents related to grave matters of national security, it’s easy to forget that Trump tried extremely hard to overturn the results of the 2020 presidential election and, when that didn’t go his way, incited a violent insurrection that left multiple people dead. But he did! In July, we learned that, according to The Washington Post, the Justice Department was investigating Trump’s actions as part of its criminal probe and that prosecutors interviewing witnesses before a grand jury had asked “hours of detailed questions about meetings Trump led in December 2020 and January 2021; his pressure campaign on [Mike] Pence to overturn the election; and what instructions Trump gave his lawyers and advisers about fake electors and sending electors back to the states.”

Crucial witnesses whom we know about have thus far included Pence’s former chief of staff Marc Short and his former chief legal counsel Greg Jacob, both of whom have significant insight into Trump’s plot to overturn the election. (Earlier this month, in what ABC News called a “dramatic escalation in the Justice Department’s investigation” of the plot to overturn the 2020 election and the riot that followed, the department subpoenaed Pat Cipollone, Trump’s former White House counsel, who attended several meetings in the run-up to January 6 in which the ex-president and his goons discussed how to keep Trump in power. Cipollone also knew of Trump’s desire to seize voting machines, which he described as “a terrible idea for the country,” “not how we do things in the United States,” and something the administration had “no legal authority” to do.)

While Trump has—you guessed it—claimed he did nothing wrong, his lawyers are reportedly “planning for criminal charges.” According to Rolling Stone, the fear of prosecution ramped up after former White House aide Cassidy Hutchinson testified publicly before the January 6 committee, at which point she told the panel that Trump had been informed that some of his supporters who’d gathered in DC on the day of the riot were armed, but demanded they be allowed in to hear his “Stop the Steal” speech anyway; that Trump assaulted a Secret Service agent after being told he couldn’t march to the Capitol himself; and that the 45th president apparently believed VP Pence “deserved” the chants calling for his hanging.

The Georgia Criminal Investigation

Remember when, as part of his plot to overturn the election, Trump made a call to Georgia secretary of state Brad Raffensperger and demanded that Raffensperger “find” him the number of votes necessary to beat Joe Biden, saying, “I just want to find 11,780 votes,” before threatening the local official over refusing his request? Fulton County district attorney Fani Willis has been investigating that and more, impaneling a special grand jury to hear evidence and potentially issue indictments. On Monday, a lawyer for Rudy Giuliani said that he’d been informed that the former mayor turned Trump attorney was a target of the investigation, while longtime Trump defender Lindsey Graham, who called Raffensperger in November 2020 to ask if he had the power to throw out mail-in ballots in certain counties, was ordered by a judge to testify before the grand jury. Speaking to The New York Times, attorney Norman Eisen, who served as special counsel to the House Judiciary Committee for Trump’s first impeachment, said he believed the Giuliani news was extremely bad for Trump. “There is no way Giuliani is a target of the DA’s investigation and Trump does not end up as one,” Eisen said.

We probably don’t have to tell you that Trump swears he did nothing wrong here, having described his Raffensperger call as absolutely “PERFECT” in May.

The Manhattan District Attorney’s Criminal Case Against the Trump Organization, Etc.

In February, Trump got a rare bit of good news on the legal front when the veteran prosecutors leading the Manhattan district attorney’s investigation of the former president’s business practices abruptly resigned, reportedly because their new boss, Alvin Bragg, had doubts about taking the case to court. Of course, according to one of those attorneys, Mark Pomerantz, that shouldn’t be taken as a sign that Trump didn’t engage in criminal activity, as Pomerantz believes he most certainly did, writing in his resignation letter that the former president was “guilty of numerous felony violations” and that it was a major “failure of justice” not to hold him accountable. (In his letter addressed to Bragg, Pomerantz added that “no case is perfect,” saying that a fear of losing a trial is not a valid reason to forgo indicting a criminal.)

Still, while the DA’s case against Trump has seemingly been put on the back burner, that doesn’t mean the guy should rest easy. In July 2021, both the Trump Organization and its longtime CFO, Allen Weisselberg, were charged with numerous crimes related to alleged tax evasion. On Monday, we learned that Weisselberg is expected to plead guilty. According to The New York Times, the Trump Organization “will not join Mr. Weisselberg in pleading guilty.”

Meanwhile, Bragg says his investigation into Trump—who swears he’s totally innocent—is still active. The Trump Organization has, like its namesake, claimed it is innocent of any wrongdoing.

The New York Attorney General’s Civil Investigation Into the Trump Organization

Last week, when Trump announced that he would be taking the Fifth as part of a previously planned, under-oath deposition, you might have wondered which investigation it involved, given that there are a comical number of them. In this civil investigation, Trump invoked his Fifth Amendment right to not answer questions being posed to him by the New York attorney general’s office, which has been investigating the Trump Organization for several years. Attorney General Letitia James said earlier this year that she’d uncovered “significant evidence” of fraud during the process. (In court filings, James’s office has alleged that the Trump Organization inflated the value of its assets when seeking loans and trying to impress people, only to deflate them when it came time to pay taxes.) Unlike in a criminal case, in a civil case a jury could use the fact that Trump pleaded the Fifth against him and infer that he has something to hide. While James’s case would not result in jail time, it could mean “steep financial penalties” for the business. James has also signaled, according to Insider, that she will “seek the dissolution of the business itself under New York’s so-called corporate death penalty—a law that allows the AG to seek to dissolve businesses that operate ‘in a persistently fraudulent or illegal manner.’”

The Westchester Criminal Investigation of the Trump Organization

The Trump Organization is also facing a criminal investigation by the Westchester County district attorney’s office, which is reportedly focused in part on whether Trump’s family business misled local officials about the Trump National Golf Club’s value with the express purpose of lowering its tax bill. (The Trump Organization has said that any suggestion it acted inappropriately is “completely false and incredibly irresponsible.”)

The DC Attorney General’s Criminal Investigation of January 6

DC AG Karl Racine is currently conducting a criminal investigation into the events surrounding the January 6 attack. In January, he said in an interview: “I think the story is clear. Donald Trump was the ringleader.”

The E. Jean Carroll Defamation Suit

Author E. Jean Carroll sued Trump for defamation in 2019 after he accused her of lying when she alleged he raped her in a New York City department store dressing room in the ’90s. Trump has shamelessly claimed that when he called Carroll a liar, he was doing so in his official capacity as president, thus making him immune from the suit.

The Mary Trump Lawsuit

Trump’s niece, Mary Trump, is currently suing him (and his sister Maryanne, and the estate of their late brother Robert) for allegedly defrauding her out of millions of dollars. Lawyers for Trump and company have claimed that, basically, she should have sued them earlier, and in September 2021, the ex-president sued his niece and The New York Times—which had previously exposed him for committing “outright fraud”—alleging they were “engaged in an insidious plot” as part of a “personal vendetta” against him. Mary responded by calling the suit an act of “desperation,” adding, of her uncle: “I think he is a fucking loser, and he is going to throw anything against the wall he can.”

The House of Representatives’ January 6 Lawsuit

Represented by the NAACP, 10 House lawmakers are suing Trump, Giuliani, and two right-wing militia groups for attempting to prevent Congress from certifying the Electoral College votes on January 6.

The Eric Swalwell Suit

The California representative is suing Trump, Giuliani, Donald Trump Jr., and Rep. Mo Brooks over the January 6 insurrection, alleging that the group violated a federal civil rights law in attempting to block the Electoral College count. Swalwell also wants the defendants held liable for encouraging violent conduct and inflicting emotional distress on the lawmakers present.

The Capitol Police January 6 lawsuits

Three separate suits by Capitol police officers have been filed against Trump for the emotional and physical injuries the officers sustained during the January 6 attack.

The Metropolitan Police January 6 lawsuit

Two members of the Metropolitan police have also sued Trump for injuries they suffered as a result of the insurrection, alleging—reasonably!—that Trump incited the riot.

The Michael Cohen lawsuit

Trump’s former “fixer,” Michael Cohen, is suing Trump (as well as the US government and various other officials) for allegedly retaliating against him after he said he was writing a tell-all about his years working for Trump.

The Class Action Lawsuit Against the Trump Biz and the Trumps

In October 2018, the Trump Organization, Donald Trump, Ivanka Trump, Don Jr., and Eric Trump were sued as part of a class action suit that alleged, per Just Security, “that the defendants used their brand name to defraud thousands of working-class individuals by promoting numerous businesses in exchange for ’secret payments.’” The suit also alleged that the defendants were “liable for a ‘pattern of racketeering activity’ violating the RICO Act,” in addition to violating “numerous state consumer protection laws concerning fair business practices and competition.”

The NAACP Legal Defense Fund Voting Rights Lawsuit

The Legal Defense Fund is currently suing Trump, the Trump campaign, and the RNC for their attempt to overturn the 2020 election, alleging that in doing so, they violated the Voting Rights Act and the Ku Klux Klan Act.

The Trump Tower Assault Lawsuit

Five individuals are suing Trump and others over the allegation that the Trump Organization’s then chief of security, Keith Schiller, hit one of them on the head when they were protesting outside of the company’s Manhattan headquarters in 2015. Last October, Trump was deposed under oath about the incident, and it was during this deposition that we learned he’s terrified of being killed by a piece of fruit.

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