President Trump is asking the federal government for billions of dollars in damages, putting his own Justice Department on the spot and creating an unprecedented ethical morass.

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.”

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.'”