Donald Trump’s Indictments, Lawsuits, and Legal Cases Explained

Nikki McCann Ramirez
·17 min read
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There are plenty of reasons Trump wants to reclaim the White House in 2024, but high on the list is the belief that as president, he will be able to sabotage the myriad criminal and civil investigations hanging over his head.

In barely a year, Trump has been indicted in four criminal cases, lost multiple civil lawsuits, and been ordered to pay hundreds of millions in damages to various parties.

Trump views the legal maelstrom surrounding his hush money payments to porn stars, unauthorized retention of classified documents, efforts to undermine the 2020 election, and allegations of corporate fraud as part of a grand conspiracy to prevent him from retaking what he feels is his rightful place as head of government. The courtroom drama has become a campaign spectacle as the former president attempts to rebrand his legal troubles as a form of “election interference.”

Trump, now the presumptive Republican nominee for president, has fashioned his campaign around the idea that he is being unfairly targeted by a vast Democratic conspiracy. He’s claimed repeatedly that he should be immune from prosecution for anything he did while in office, while suggesting he will weaponize the Justice Department to prosecute President Joe Biden, as well as many of those involved in his legal cases, should he retake the White House.

The list of probes, prosecutors, trials, court rulings and government bodies investigating the former president is long, and takes on a bewildering level of complexity when one factors in the nearly constant stream of subpoenas, letters, lawsuits, and insider reports emerging on a near-daily basis.

In April, the first of Trump’s criminal trials — over his alleged 2016 hush money payments to porn star Stormy Daniels — will kick off in Manhattan, New York. To help make heads or tails of what exactly Trump has been charged with when pending cases are likely to move forward, and what’s already happened, we’ve prepared a guide to the six biggest cases against Trump — and the potential consequences they may bring.

Paying Off a Porn Star

Trump made history last April by becoming the first president to be arrested and charged in a criminal case. He pleaded not guilty to 34 separate felony counts of falsifying business records brought by Manhattan District Attorney Alvin Bragg.

The criminal trial — the first ever for a former president — is set to begin on Monday, April 15, just over a year after the charges were brought.

The charges relate to a 2016 hush-money payment made at Trump’s direction to adult film actress Stormy Daniels. Two weeks before the election, Trump allegedly instructed his former attorney, Michael Cohen, to provide Daniels with $130,000 in order to buy her silence regarding an alleged affair and stave off a scandal in the final days of his campaign. Prosecutors allege the payment — which was made through a personal loan taken out by Cohen and routed through a shell corporation with a promise from the Trump Organization that the funds would be reimbursed — constitutes an unreported campaign expense.

The former president took steps to ensure that his self-surrender in Manhattan could be exploited as a self-serving public spectacle. As previously reported by Rolling Stone, Trump insisted on a high-profile arrest in order to create, as one source put it, his own “Jesus Christ” moment and galvanize his supporters into viewing him as a martyr for their cause. In the days after his booking, Trump raised more than $7 million in a campaign cash grab.

Trump has reacted to the case with characteristic ire. His public attacks against prosecutors and the case itself led Judge Juan Manuel Merchan to issue a not-a-gag-order against Trump in April of last year that, while allowing him to publicly discuss the case, restricts his access to evidence and prevents him from publicly sharing materials disclosed to him or his legal team during the course of the trial.

Last July, Judge Alvin Hellerstein slapped down a bid by the former president to have the trial moved from state to federal court. Hellerstein wrote that “Trump has failed to show that the conduct charged by the Indictment is for or relating to any act performed by or for the President under color of the official acts of a President. Trump also has failed to show that he has a colorable federal defense to the Indictment.”

Trump’s trial was originally scheduled to begin in New York on March 25, 2024, but was delayed to April 15. As the start date for his first criminal trial approached, the former president began lashing out at the family of Judge Merchan. “He hates me!” Trump wrote in March of Merchan, before going after his daughter. “She works for Crooked Joe Biden, Kamala Harris, Adam ‘Shifty’ Schiff, and other Radical Leftists who Campaign on ‘Getting Trump, and fundraise off the ‘Biden Indictments,’” he wrote.

In response, Merchan placed an explicit gag order on the former president barring him from publicly attacking witnesses, prosecutors, court staff, and jurors involved in the case. Needless to say, if he’s trying to make a good impression with the judge who will oversee his trial, it’s not going well.

The trial will be an extremely high-profile affair, featuring some of the most prominent individuals from Trump’s administration and 2016 campaign. Former Trump lawyer and professional fixer Michael Cohen, as well as former White House Communications Director Hope Hicks, will reportedly testify as witnesses. Daniels, the woman at the center of the scandal, has previously stated that she’s “absolutely ready” to take the stand herself. Trump himself is compelled to attend the trial as a defendant, and given his track record one can expect at least a few courtroom antics from the former president.

Election Interference and Jan. 6

On August 1, the Justice Department charged Trump on four counts related to Special Counsel Jack Smith’s investigation into the former president’s efforts to overturn the 2020 election, and the violent riot that took place in the Capitol on Jan. 6.

The charges included conspiracy to defraud the United States, conspiracy to obstruct an official proceeding, obstruction of and attempt to obstruct an official proceeding, and conspiracy against rights. Trump pleaded not guilty to the charges.

In his indictment, Smith wrote that following his election loss, Trump “pursued unlawful means of discounting legitimate votes and subverting the election results.”

Alongside Trump, the indictment referenced six unindicted co-conspirators, later identified as Rudy Giuliani, Trump attorneys John Eastman and Sidney Powell, former Justice Department Acting Assistant Attorney General Jeffrey Clark, and Ken Chesebro.

Smith’s investigation extended well beyond Trump. The special counsel has subpoenaed everyone from former Vice President Mike Pence to ex-Trump adviser Steve Bannon, with Mark Meadows also reportedly serving a key role in both of Smith’s investigations. The former Trump chief of staff was present at a now-infamous Dec. 2020 Oval Office gathering that has been reported to be a focus of the investigation. Former White House Counsel Pat Cipollone, Trump attorneys Rudy Giuliani and Sidney Powell, and former National Security Adviser Michael Flynn also attended the meeting, during which participants allegedly discussed desperate, last ditch efforts to ensure Trump would remain in power, including seizing voting machines and invoking martial law. In a press conference announcing the charges against Trump, Smith indicated that the “investigation of other individuals continues,” and further charges may be pending.

Prosecutors are also probing allegations that the former president and his allies defrauded donors by touting false claims of election fraud. Smith issued dozens of wide-ranging subpoenas for records of fundraising emails — including drafts, and suggested edits from campaign staff — as well as records of any discussions about fundraising communications and campaign messaging strategy. The investigation has also dug into Trump’s efforts to meddle with election results in individual states, including Georgia, Arizona, Michigan, Nevada, New Mexico, and Pennsylvania.

Trump has challenged the indictment on grounds that he has immunity from any crimes he may or may not have committed while in office. Trump’s legal team has sought court ruling affirming their immunity argument, and in January, claimed before the D.C. Federal Court of Appeals that — under their interpretation of the law — the president would “have to be speedily impeached and convicted” before a criminal prosecution could occur — even if the crime in question was something like using S.E.A.L. Team Six to assassinate a political rival.

The argument was rejected by the D.C. Appeals Court and kicked up to the Supreme Court, which will hear oral arguments on the case in late April. In preparation, Trump’s allies filed an amicus brief with the court last month arguing that the justices should not consider hypothetical scenarios in which the president orders the execution of his rivals when making their decision.

The original March 4 trial date for the case has been indefinitely postponed pending the resolution of the immunity question. “The court will set a new schedule if and when the mandate is returned,” Judge Tanya Chutkan wrote in her February order.

Classified Documents at Mar-a-Lago

Last August, FBI agents executed a search warrant at Trump’s Mar-a-Lago residence in Palm Beach, Florida. Authorities seized hundreds of classified documents retained by the former president following his departure from the White House. The raid was the culmination of a monthslong effort by the National Archives and federal authorities to recover the missing materials. The effort included a subpoena and the DOJ visiting Mar-a-Lago to recover the documents — to no avail, precipitating the raid.

Trump and his legal team went to great pains — even petitioning, unsuccessfully, to the Supreme Court — to prevent investigators from actually seeing what was in the documents he was hoarding in his home.

On June 8, Smith leveled a 37 count indictment against Trump. His longtime aide Walt Nauta was charged alongside him on six criminal counts. Authorities alleged that Trump had not only unlawfully retained highly classified documents after leaving office, but also showed some of these documents to individuals who lacked the security clearance to view them. Furthermore, Trump is accused of having conspired to hide or destroy the documents to avoid handing them over to federal authorities. Trump pleaded not guilty on all counts at a Miami federal courthouse the following week.

In the last days of July, Smith threw Trump another curveball, issuing a superseding indictment that leveled additional charges against Trump and Nauta, as well as charging a second Mar-a-Lago employee, Carlos de Oliveira. The DOJ alleges that the three men conspired to destroy Mar-a-Lago security footage that had been subpoenaed by investigators.

Much like in his federal election interference case, Trump has claimed prosecutorial immunity as the reason he should skirt charges — alongside several other implausible legal arguments. These include that he could declassify documents telepathically, that the classified materials were actually his personal property, and his scrap paper.

The case was originally expected to go to trial in May 2024 — months before the presidential election — but the former president has repeatedly submitted unsuccessful motions to indefinitely delay the trial, and there’s no clear start date in sight.

Judge Eileen Cannon, whom Trump appointed to the U.S. District Court for the Southern District of Florida in 2020, has been criticized for her apparent indecision and slow-walking of major decisions in the case. On April 3, Smith went toe-to-toe with Cannon over her requests for jury instructions, arguing that her request that the prosecution and defense entertain the idea that Trump was allowed to retain classified documents as personal material under the Presidential Records Acts blatantly contradicted established law.

Assaulting and Defaming E. Jean Carroll

Trump made history last May when he became the first president to be found liable for sexual battery in a civil court case brought by author E. Jean Carroll, who alleged that the former president had raped her in the ‘90s.

While Trump will not serve any jail time in this case, a Manhattan jury ruled in May that Trump was liable for sexual battery and defamation against Carroll, ordering him to pay $5 million in damages. Trump was once again found liable for defaming Carroll in September, and in January a Manhattan jury ruled that the former president owed Carroll $83.3 million in total damages after deliberating for less than three hours.

Why such a hefty sum? Well, the day after the ruling last May, Trump appeared on CNN for a town hall event, during which he repeated many of the attacks against Carroll that had originally motivated her to sue him for defamation. The former president mocked Carroll and bragged that he was too famous to have been publicly shopping at the department store where the alleged assault took place.

In response, Carroll filed for additional damages from Trump, expanding the scope of her second, separate 2019 lawsuit against him. “It makes a mockery of the jury verdict and our justice system if he can just keep on repeating the same defamatory statements over and over again,” Roberta Kaplan, Carroll’s attorney, said of Trump’s comments. A judge granted her request in June, and the jury in her pending defamation suit will be allowed to consider the additional penalties.

In June, Trump’s attorneys requested a retrial for the former president on the original May ruling, which was denied In July. U.S. District Judge Lewis Kaplan torched the former president’s arguments that the financial penalties were too high because the jury determined that he had assaulted, but not legally raped, Carroll.

“The definition of rape in the New York Penal Law is far narrower than the meaning of ‘rape’ in common modern parlance,” Kaplan wrote in his decision. “The finding that Ms. Carroll failed to prove that she was ‘raped’ within the meaning of the New York Penal Law does not mean that she failed to prove that Mr. Trump ‘raped’ her as many people commonly understand the word ‘rape.’ Indeed, as the evidence at trial recounted below makes clear, the jury found that Mr. Trump in fact did exactly that.”

Not one to take things lying down, Trump has appealed both rulings — but in the aftermath of his second trial was forced to post a $91.6 million bond in order to do so. Given that he continues to attack Carroll despite having already lost two defamation cases to her, the chances he’ll manage to overturn on appeal look slim. In fact, Carroll and her team have indicated she’s willing to take him to court as many times as necessary until he cuts the shit.

Election Meddling in Georgia

In the aftermath of the 2020 election, Trump attempted to undermine the results of various key swing states in order to undermine the election. Georgia was one such state.

Fulton County District Attorney Fani Willis empaneled a grand jury in May 2022 to investigate Trump and his allies’ efforts to interfere with the state’s outcome, including efforts to pressure Secretary of State Brad Raffensperger to rig the election in his favor.

“There’s nothing wrong with saying, you know, um, that you’ve recalculated,” Trump told Raffensperger during a January 2021 phone call. “I just want to find 11,780 votes, which is one more than we have. Because we won the state.”

An indictment, which could include charges against Trump, could come as soon as August. Sources told The Washington Post in June that Willis has expanded the probe into some of Trump and his allies’ activities in other states, and is considering invoking Georgia’s Racketeer Influenced and Corrupt Organization (RICO) laws to level racketeering charges against those involved.

In August, Trump and 18 of his allies were indicted in a widespread racketeering case over their alleged efforts to meddle with the state’s election. Trump himself was charged with 41 total counts, prominent figures in the Trump administration — including Rudy Giuliani, John Eastman, Mark Meadows, and Ken Chesebro — have also been charged.

Notably, Georgia prosecutors became the first among Trump’s four criminal indictments to release a mugshot — a first for a former president.

The case has moved slowly, with no set start date for a trial in view. Four defendants — including MAGA attorney Sidney Powell and coup plotter Ken Chesebro — have already pleaded guilty, while three others have split their cases from the state into federal court.

At one point, it looked like Willis’ case might fall apar. In January, Trump co-defendant Mike Roman accused Willis of engaging in an improper romantic relationship with Nathan Wade, who was hired to assist in the prosecution of the case and paid over $600,000 for his work. Roman requested that Willis be removed from the prosecution, and the case against him dismissed, on grounds that the affair presented a conflict of interest.

After a long investigation by the court into Willis and Wade’s affair, Georgia Superior Court Judge Scott McAfee ruled in March that the evidence against the pair was “legally insufficient to support a finding of an actual conflict of interest,” and that Willis could remain on the case so long as Wade stepped aside.

Corporate Fraud in New York

In Sept. 2022, New York Attorney General Letitia James brought a $250 million civil fraud case against the former president, his children, and members of the Trump Organization. James alleged that the Trump Organization made “over 200” false valuations of assets over the past decade. She also said she planned to make referrals to the IRS criminal division and the U.S. Attorney’s Office for the Southern District of New York for possible federal crimes.

In September, Judge Arthur Engoron ruled that Trump, his two adult sons, and several of his associates were liable for fraud. The ruling established that Trump had overvalued his properties and inflated his net worth over several years, thus deceiving banks, investors, and insurers. The subsequent trial, which took place between Oct. of 2023 and Jan. 2024, established that Trump owed $355 million in damages to the state and barred the former president “from serving as an officer or director of any New York corporation or other legal entity in New York for a period of three years.”

Trump planned to appeal the ruling and needed to post a $454 million bond to prevent the state from seizing his assets while he did so. James had previously told ABC News that the state would not hesitate to seize Trump’s properties as payment if necessary. Trump’s own lawyers wrote in February that the former president may have had to sell some of his real estate portfolio to cover the fines.

After being rejected by dozens of underwriters — and begging his followers for cash — Trump was granted a last-minute bail-out by a New York appeals court, which drastically reduced the amount of the bond to just $175 million.

Now that the former president has posted the bond, he’s delayed the enforcement of the ruling against him, and (at least temporarily) skirted accountability for his actions.

James also secured a conviction against a member of Trump’s inner circle. The attorney general brought a separate criminal, tax fraud case against former Trump Organization Chief Financial Officer Allen Weisselberg in May 2021. Weisselberg was ultimately sentenced to five months in prison after pleading guilty to failing to declare and pay taxes on more than $1.7 million in company benefits provided by the Trump Organization. In April, Weisselberg was sentenced to an additional five months in prison over charges of perjury relating to his testimony in the civil fraud suit.

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