Of all the ways President Trump has pushed the boundaries of executive power, one stands out to lawyers and watchdogs.
The president wants the government he leads to pay him billions of dollars.
Trump has filed multiple claims arguing he's been hurt by Justice Department investigations and the leak of his tax returns years ago. Now it's up to his own political appointees to determine whether to settle with their boss — and for how much taxpayer money.
"There is a glaring conflict of interest with Trump being on both sides of the claim," said Edward Whelan, a former lawyer at the Justice Department and a political conservative who once clerked for the late Justice Antonin Scalia. "It is outrageous that he and those answering to him would be deciding how the government responds to these extravagant claims."
Unfinished business
For Trump, filing lawsuits, including those that are frivolous or where he has little chance of success, has long been standard operating procedure, a way of communicating displeasure. A White House official, speaking on background because he was not authorized to speak on the record, said these claims amount to unfinished business for the president.
It's clear they have been weighing on his mind. In December, Trump was in North Carolina nearing the end of a speech about the economy when out of nowhere, he started talking about the FBI search of his Florida resort in 2022.
"I had these animals trying to attack me at Mar-a-Lago," he said. "They went into my wife's closet."
Federal agents seized classified documents from a bathroom, a ballroom and an office, part of a sprawling and court-approved investigation into unlawful retention of government secrets and alleged obstruction of justice.
The president viewed that search as an attack, part of an ongoing weaponization of the government against him personally. So, he filed a claim with the Department of Justice, seeking $230 million over the Florida operation and an earlier probe into his campaign's ties to Russia.
"And they do say that, you know, it's never been a case like this," the president said at a rally this December, taking on the animated voice of a newscaster. "'Donald Trump sues the United States of America. Donald Trump becomes president. And now Donald Trump has to settle the suit.'"
Trump was out of office when the administrative claims were first filed. The Russia investigation ended with no charges against Trump. Then, after he won the 2024 election, the Justice Department abandoned its appeal of the classified documents case against him in Florida. And now Trump finds himself on both sides of the dispute.
"But isn't that a strange position to be in," the president said at the rally. "I've gotta make a deal. I negotiate with myself."
"An order of magnitude greater"
There's a process in place at the Justice Department for people who say they've been harmed by the federal government.
In the normal course of business, those claims get evaluated by career lawyers. They rarely involve high profile criminal investigations like Trump's.
"Some of them are run of the mill, right?" said Rupa Bhattacharyya, a former Justice Department lawyer who evaluated these kinds of allegations. "Postal vehicles get into traffic accidents, VA doctors have malpractice claims brought against them, people slip and fall in federal buildings."
Even in the most serious cases, like ones that involved injuries to people cleaning up after the terrorist attack on Sept. 11, 2001, Bhattacharyya said the payouts almost never amounted to more than $10 million.
Trump wants a lot more than that — 23 times more — for the Justice Department investigations against him.
"Two hundred thirty million dollars would be an order of magnitude greater than any administrative settlement the department has ever agreed to in a Federal Tort Claims Act case," said Bhattacharyya.
Typically, the Justice Department would fight claims in court and defend the work of its career prosecutors and FBI agents. And in this case, they would have strong legal defenses. After all, a federal judge approved the search of Trump's Mar-a-Lago property — finding probable cause.
Given how much money is at stake, people at the top of the Justice Department would make the final call. And that adds another complication.
Attorney General Pam Bondi and Todd Blanche, her deputy, both used to work as Trump's personal attorneys. The third-in-command at Justice, Stanley Woodward, represented Trump's valet, who was charged as an alleged co-conspirator in the Mar-a-Lago case.
"The fear that many have is that the Department of Justice will simply fold and ask Donald Trump the individual how much money Donald Trump's administration should funnel to him," said Whelan, the former DOJ lawyer.
In a recent interview with NBC's Tom Llamas, Trump didn't do anything to bat down the suggestion that he would be the final decider. "Well, what I would do, tell them to pay me but I'll give 100% of the money to charity," the president said.
A $10 billion lawsuit
But Trump wasn't just upset about those old Justice Department investigations. He had more scores to settle. Last month he filed another claim against the federal government, a $10 billion lawsuit over the 2019 leak of his tax returns by a contractor for the Internal Revenue Service.
Experts in tax law say that case has some big flaws. For one thing, the statute of limitations seems to have expired. What's more, the leak took place during Trump's first term in office, so the president is suing the government for actions that occurred when he was in charge. The contractor is currently serving prison time for the leak.
Congressional Democrats pressed top administration officials about the IRS case in recent weeks. Treasury Secretary Scott Bessent told lawmakers it was an issue for the Justice Department, which is defending the Treasury and IRS in the case.
In a separate hearing, Attorney General Bondi didn't shine any additional light, telling a senator she would not discuss pending litigation.
A Justice Department spokesperson told NPR: "In any circumstance, all officials at the Department of Justice follow the guidance of career ethics officials."
Last summer, Bondi fired the top in-house ethics lawyer at the Justice Department, after he said he raised questions about gifts and tickets to her.
Taxpayer-funded settlement
Whelan, the conservative lawyer, said one solution is to pause the IRS case until Trump is no longer president.
If the Justice Department eventually approves a settlement, the money would come from something called the judgment fund, a taxpayer funded pot of money.
Bhattacharyya said that means "the American people are on the hook for these claims if liability is assessed against the government."
A spokesman for Trump's private legal team said in a statement, "The IRS wrongly allowed a rogue, politically-motivated employee to leak private and confidential information about President Trump, his family, and the Trump Organization to the New York Times, ProPublica and other left-wing news outlets, which was then illegally released to millions of people. President Trump continues to hold those who wrong America and Americans accountable."
Pressed during a recent press gaggle on Air Force One on whether it is fair to ask the American people to pay out such a large settlement, Trump dismissed any concern, insisting that anything he wins would go to charity.
"They give money to charity anyway," Trump said. "They give $40 billion a year to charity, our government."
It's unclear where Trump pulled that number. The White House did not respond to questions about it or which charities would get the money.
But at a time when Americans say their top concern is the cost of living and making ends meet, the idea of the president receiving a massive windfall from the government he leads may not sit well with voters — even if it is donated to charity.
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