Timeline: Letitia James And Donald Trump's Heated Court Battles
A Timeline Of Donald Trump And Letitia James’ Heated Court Battles
President Donald Trump and New York Attorney General Letitia James have spent years locked in high-stakes legal battles over Trump’s business dealings, alleged fraud, and policies, but tensions escalated sharply on Oct. 9, when federal prosecutors, following weeks of pressure from Trump, finally indicted James on charges of fraud and making false statements.
According to the New York Times, the indictment, filed Thursday in the Eastern District of Virginia, alleges that James misrepresented her intent to use a Norfolk, Virginia, home as a secondary residence when she allegedly intended to rent it out as an investment property. That misrepresentation, prosecutors claim, allowed her to secure more favorable mortgage terms, saving nearly $19,000.
The charges follow the Trump-directed indictment of former FBI Director James Comey just two weeks earlier, intensifying concerns over the president’s direct involvement in the justice system and raising alarms about the erosion of long-standing democratic norms amid what critics call a campaign of political retribution.
On Thursday, James swiftly denied wrongdoing, calling the charges “baseless.”
“This is nothing more than a continuation of the president’s desperate weaponization of our justice system. He is forcing federal law enforcement agencies to do his bidding, all because I did my job as the New York State Attorney General,” she said in a statement.
“These charges are baseless, and the president’s own public statements make clear that his only goal is political retribution at any cost. The president’s actions are a grave violation of our Constitutional order and have drawn sharp criticism from members of both parties. His decision to fire a United States Attorney who refused to bring charges against me – and replace them with someone who is blindly loyal not to the law, but to the president – is antithetical to the bedrock principles of our country.”
The tension between these two public figures doesn’t appear to be letting up anytime soon. Let’s take a look back at Donald Trump and Letitia James’ contentious court history over the years.
November 2019
In June 2018, the New York Attorney General filed a lawsuit against the Donald J. Trump Foundation, alleging that its directors had failed to fulfill their fiduciary responsibilities under state charity laws. The suit detailed how Donald Trump repeatedly used the Foundation’s funds to serve his personal, business, and political interests, including unlawfully coordinating with his 2016 presidential campaign.
The lawsuit claimed that during the first half of 2016, amid the Republican primaries, Trump leveraged Foundation money raised from public donations to project an image of generosity. Just days before the Iowa caucuses, his campaign distributed $500,000 at a rally and later claimed credit for the Foundation’s full $2.8 million in grants, blurring the line between charity and campaign strategy, according to the suit.
As part of a settlement reached in 2019, Trump admitted to personally misusing Foundation funds and agreed to specific restrictions should he attempt to form another charitable organization. He also consented to ongoing oversight by the Attorney General’s office. His children—Donald Trump Jr., Ivanka Trump, and Eric Trump—were required to complete mandatory training on nonprofit governance. The agreement also designated which charities would receive the Foundation’s remaining assets as part of its formal dissolution.
December 2021
Before she officially filed her historic 2022 landmark civil fraud lawsuit, Trump and his organization sued Letitia James in federal court in 2021, trying to halt her investigation into his business dealings. In his 2021 suit, the Republican claimed political bias and due process violations.
Ironically, the lawsuit was filed two weeks after James requested that Trump sit for a Jan. 7 deposition. He argued that her investigation, focused in part on how the Trump Organization valued its assets, violated Trump’s constitutional rights and amounts to a “thinly veiled effort to publicly malign” him and his associates, according to court documents obtained by NPR.
Trump’s legal team portrayed James, a Democrat, as harboring “personal disdain” for him, citing public statements she made over the years, including her participation in “die-in” protests against him, her campaign boast of suing his administration 76 times, and tweets from 2018 declaring she had her “eyes on Trump Tower” and that Trump was “running out of time.”
September 2022
In 2022, James filed a landmark civil fraud lawsuit against Trump, three of his adult children, and senior executives of the Trump Organization, alleging that they had engaged in a years-long scheme to fraudulently inflate the value of their assets. The goal, according to the lawsuit, was to deceive lenders, insurers, and tax authorities in order to secure better loan terms, favorable insurance rates, and lower tax liabilities.
The lawsuit alleged that Trump, his companies, and his family committed nearly $250 million in fraud and called for the Trumps to be permanently barred from holding executive positions in any New York-based company.
Notably, in May of that year, federal Judge Brenda Sannes dismissed Trump’s 2021 lawsuit against James, allowing her civil investigation to continue.
February 2024
A landmark verdict for James’ civil fraud lawsuit was delivered in 2024. The New York City AG won a judgment ordering Trump, his sons, companies, and other related parties to pay more than $450 million for fraudulently inflating his net worth.
Trump was banned from serving as an officer or director of any New York company for three years. The Republican and his companies were also banned from applying for loans from any New York bank or financial institution for three years.
August 2025
Sadly, in August 2025, a New York appeals court tossed out the civil fraud judgment handed down to the president, his companies, and family. While the more than half-billion-dollar fine has been waived, the ruling still prohibits Donald Trump and his sons, Eric and Donald Jr., from holding executive roles in any company for several years, as previously reported.
A five-judge panel reviewing Trump’s appeal in August failed to reach a consensus on several key issues but unanimously agreed that the original civil penalty was “excessive.”
April 2025
In April, Letitia James highlighted the extensive legal efforts her office had taken to defend New Yorkers against what she described as “dangerous and illegal” federal policies carried out by Trump. Since Jan. 20, James revealed she had filed or joined 15 lawsuits and submitted 22 amicus briefs in collaboration with Democratic attorneys general across the country. These legal actions, she claimed, successfully halted several of the Trump administration’s most harmful initiatives. The efforts spanned a wide range of issues, including the defense of birthright citizenship, protection of federal workers, and the preservation of access to education, healthcare, and voting rights.
“We will not allow this administration to trample our Constitution, strip Americans of their fundamental rights, and dismantle critical services that millions of people rely on every day,” said Letitia James. “We stopped some of their most unconstitutional policies dead in their tracks, and we are not slowing down. If this administration continues to bulldoze the Constitution and ignore the law, they will find all of us standing in the way every single time.”
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