A Timeline Of Donald Trump And Letitia James’ Heated Court Battles

Former President Donald Trump and New York Attorney General Letitia James have been locked in a series of fierce legal showdowns for years. Their ongoing feud—rooted in investigations, lawsuits, and accusations of political retribution—reached a new level on October 9, 2025, when federal prosecutors indicted Letitia James on charges of fraud and false statements.


Federal Indictment of Letitia James

According to The New York Times, the indictment, filed in the Eastern District of Virginia, alleges that James misrepresented her intent to use a Norfolk, Virginia home as a secondary residence. Prosecutors claim she actually intended to rent it as an investment property, allegedly securing a $19,000 financial advantage through favorable mortgage terms.

The indictment came just weeks after former FBI Director James Comey faced charges under similar circumstances, intensifying fears about Trump’s influence over the justice system and what critics call a pattern of political retribution.

James, however, denied any wrongdoing, calling the charges “baseless” and politically motivated.

“This is nothing more than the president’s weaponization of our justice system,” James said in a statement. “He’s forcing federal agencies to act as his personal enforcers because I held him accountable as New York’s Attorney General.”


Trump vs. Letitia James: A Legal History

The Trump–James rivalry has unfolded through several major lawsuits and court rulings. Here’s a look at their legal timeline.


November 2019: The Trump Foundation Case

In June 2018, Letitia James filed a lawsuit against the Donald J. Trump Foundation, alleging that Trump and his children misused charitable funds for personal and political gain. The lawsuit claimed that Trump diverted Foundation money to support his 2016 presidential campaign, including a $2.8 million fundraiser disguised as a charitable event.

In 2019, the case ended in a settlement requiring Trump to admit to misusing funds and placing restrictions on future charity activities. His children—Donald Jr., Ivanka, and Eric Trump—were ordered to complete nonprofit governance training, and the Foundation was officially dissolved.


December 2021: Trump Sues Letitia James

Before James could file her landmark civil fraud case, Donald Trump preemptively sued Letitia James, accusing her of political bias and violating due process. Trump’s lawsuit sought to block her investigation into his business practices.

He claimed that James’s probe into the Trump Organization’s asset valuations was unconstitutional and politically motivated. Court documents highlighted James’s public criticism of Trump and her 2018 campaign statements about “having [her] eyes on Trump Tower.”

The lawsuit was dismissed in May 2022 by a federal judge, allowing James’s investigation to proceed.


September 2022: The Civil Fraud Lawsuit

In 2022, James filed a civil fraud lawsuit against Donald Trump, three of his adult children, and top Trump Organization executives. The lawsuit alleged a decade-long scheme to inflate asset values in order to secure loans, reduce taxes, and mislead insurers—a scheme totaling $250 million in fraud.

James sought to ban the Trumps from executive positions in New York-based companies and impose heavy financial penalties. The lawsuit became one of the most consequential legal challenges of Trump’s career.


February 2024: The Landmark Judgment

In 2024, Letitia James secured a major victory when a New York court ruled against Trump, ordering him, his companies, and his sons to pay over $450 million in penalties. The ruling also barred Trump from holding executive roles or seeking loans from New York banks for three years.

This decision marked a significant legal and political blow to the former president.


August 2025: The Appeals Court Reversal

In August 2025, a New York appellate court overturned the civil fraud judgment, waiving the $450 million fine but upholding restrictions preventing Trump and his sons from leading companies in New York.

The five-judge panel described the original penalty as “excessive” but agreed that some level of accountability was appropriate.


April 2025: James Defends Her Record

Earlier in April 2025, Letitia James highlighted her office’s ongoing efforts to challenge Trump administration policies she described as “dangerous and illegal.” She reported joining 15 lawsuits and submitting 22 amicus briefs alongside other Democratic attorneys general, addressing issues like citizenship rights, worker protections, and voting access.

“We stopped some of their most unconstitutional policies dead in their tracks,” James said. “If this administration keeps bulldozing the Constitution, they’ll find all of us standing in the way.”


Conclusion: An Ongoing Legal Feud

The conflict between Donald Trump and Letitia James continues to shape national headlines. What began as a series of lawsuits has evolved into a full-blown political and legal war—testing the limits of American democracy, judicial independence, and political accountability.

 

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