NEW YORK (AP) — The day she was elected New York’s attorney general, Letitia James blasted President Donald Trump as a “con man” and “carnival barker” and pledged to scrutinize his public policies and personal business dealings. As James mounted a lawsuit claiming that Trump’s business persona was built partly on lies, he returned fire, calling her “grossly incompetent” and “an evil person.”

James, a Democrat, and Trump, a Republican, have long been legal and political foes, tangling in dozens of lawsuits over the years.

On Thursday, Trump’s Justice Department indicted James on mortgage fraud charges after he vowed revenge on his enemies, escalating a feud that has persisted since she campaigned for attorney general in 2018. She has denied wrongdoing.

Here’s a look at some of James and Trump’s legal tussles:

A lawsuit accusing Trump of lying about his wealth

James sued Trump after his first term, alleging in September 2022 that he inflated his net worth by billions of dollars by misleading banks and insurers about the value of assets such as Trump Tower and the Mar-a-Lago property in Florida. She dubbed it “The art of the steal,” a twist on the title of Trump’s memoir. After a trial, a judge ordered Trump last year to pay a massive monetary penalty. An appeals court later threw out the penalty, which had grown to more than $500 million with interest, but affirmed a lower-court finding that Trump committed fraud. James is now asking the state’s highest court to reinstate the penalty, while Trump is seeking to have other non-monetary punishments lifted.

Face-to-face at a deposition, fireworks in a courtroom

Trump sparred with James at a deposition for her civil fraud lawsuit in April 2023. Answering questions for seven hours at her Manhattan office, he told her that “the whole case is crazy” and accused her staff of trying to trip him up like fictional TV lawyer Perry Mason did to witnesses. A few months later, they came face-to-face again as Trump testified at trial. Trump looked away from James and scowled as he walked past her on the way into court. On the witness stand, he accused her of pursuing him to advance her career. “She’s a political hack, and this is a disgrace that a case like this is going on,” he testified, adding that James “should be ashamed of herself.”

A leading role fighting Trump administration policies

Working with a coalition of Democratic state attorneys general, James sued Trump and his administration multiple times since he returned to the White House in January, challenging everything from cuts to funding for counterterrorism and public safety to plans to deploy National Guard troops in Oregon. Those efforts began the day after Trump took office with a lawsuit challenging his effort to overturn birthright citizenship. Other lawsuits have challenged the work of Elon Musk’s so-called Department of Government Efficiency, mass firings of federal workers and the revocation of temporary protected status for Venezuelans.

Dozens of lawsuits in Trump’s first term

During his first term, James sued the administration at least 66 times in a two-year span, challenging policies on environmental, immigration and education policy, health care and other issues. She fought his plans to include a question about immigration status on the Census, winning in the U.S. Supreme Court, and sued the U.S. Postal Service over slowdowns before the 2020 election. Other major victories during the first term included restoring what’s known as Deferred Action for Childhood Arrivals or DACA, which allows people who came to the country unlawfully as children to remain, and a ruling that barred immigration authorities from arresting people at courthouses.

Helping build a criminal case against Trump’s company

James teamed with then-Manhattan District Attorney Cyrus Vance Jr. to bring tax fraud charges against the Trump Organization and Allen Weisselberg, its chief financial officer. The company was convicted in 2022 of helping its executives dodge taxes on extravagant perks such as Manhattan apartments and luxury cars. James assigned two lawyers to work with Vance’s office after uncovering evidence of potential criminal wrongdoing. James was not involved when Trump was prosecuted last year by Alvin Bragg, the current District Attorney, and convicted of falsifying business records.

Closing down Trump’s charity over misspending

In 2019, James finalized an agreement brokered by her predecessor dissolving his charitable foundation and forcing him to pay $2 million to various nonprofits as a fine for misspending funds to further his political and business interests. The Trump Foundation’s $1.7 million in remaining funds were also given away. Trump acknowledged in a court filing that he allowed campaign staff to coordinate with the charity for a veterans fundraiser before the 2016 Iowa caucuses. He also admitted to arranging for it to pay $10,000 for a 6-foot (1.8-meter) portrait of him and the spending of $11,525 in foundation funds on sports memorabilia and Champagne at a charity gala.

Trump fights back, but judges reject his lawsuits

Trump sued James in 2021 in an attempt to block her from investigating him and his businesses. After a federal judge in New York quickly threw out the case, Trump sued her again in Florida. A judge there refused to block the probe, writing in December 2022: “This litigation has all the telltale signs of being both vexatious and frivolous.” Trump abandoned efforts to revive his first lawsuit against James after the Florida judge rejected a lawsuit he filed against his 2016 presidential election rival Hillary Rodham Clinton. In tossing that case, U.S. District Judge Donald M. Middlebrooks ordered Trump and one of his lawyers — Alina Habba, currently acting U.S. attorney in New Jersey — to pay nearly $1 million for filing frivolous lawsuits for political purposes, which the judge said amounted to a “pattern of abuse of the courts.”

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Izaguirre reported from Albany, New York.