This time a year ago, Dana Boente was something of a conservative darling. The veteran federal prosecutor had just stepped in to defend President Trump’s entry ban after the acting attorney general was fired over her refusal to do so. He would go on to serve, temporarily, in the country’s two top law enforcement jobs and seemed to earn Trump’s gratitude.

“Dana, I just want to thank you on behalf of the government, on behalf of our country, for leading a strong, strong effort in the courts,” Trump told Boente last February. “We really appreciate it; believe me.”

That appreciation might be dissipating, though, after Republicans revealed in a controversial memo released last week that Boente had signed a secret court application to surveil a former Trump campaign adviser. At the time, Boente was acting as the deputy attorney general in Trump’s administration, according to the memo.

Conservatives have said that surveillance application was flawed because it did not reveal that some information contained in it was funded by Hillary Clinton’s presidential campaign and the Democratic National Committee. Trump has said, “A lot of people should be ashamed of themselves, and much worse than that.”

Boente’s signature on the application could complicate Republicans’ effort to portray the surveillance as politically motivated, given his past service to the Trump administration.

“I think it sort of undercuts any suggestion that this was a politically motivated document designed by people who are against President Trump,” said Barbara McQuade, who was a U.S. attorney in the Obama administration at the same time as Boente and is now a University of Michigan law professor.

Of Boente, she said: “I think he’s largely seen as a nonpartisan, independent prosecutor . . . he dutifully follows orders. He does what he thinks he’s supposed to do.”

Boente, 64, who now works as general counsel at the FBI, is not the only high-level official to authorize surveillance of former Trump campaign operative Carter Page, nor is his signature the only mark against GOP claims about its propriety.

Deputy Attorney General Rod J. Rosenstein, who was appointed to his post by Trump, also signed an application — which contained additional information beyond that paid for by the Clinton campaign and also revealed some of its material had a political funder.

The Republican memo, produced by House Intelligence Committee Chairman Devin Nunes (R-Calif.), details what it claims are findings that “raise concerns with the legitimacy and legality of certain DOJ and FBI interactions with the Foreign Intelligence Surveillance Court” and “represent a troubling breakdown of legal processes.” Even before it was publicly released, though, the FBI had disputed it, saying in a statement the bureau had “grave concerns about material omissions of fact that fundamentally impact the memo’s accuracy.”

The FBI declined to comment for this story.

Boente’s inclusion in the memo is particularly notable because he is the only high-level Justice Department official identified who, before the document was released, had not drawn Trump’s public scorn. His move in recent weeks to the FBI was supported by Attorney General Jeff Sessions, who — like Trump — has called for leadership changes at the bureau and who said in a recent interview with the Washington Times that he “believed it was important to have a fresh start at the FBI.”

Boente’s job now is a career — rather than a political — position, meaning he cannot be removed at will by Trump. But at least one conservative website suggested in recent days that he “may have to step down” over the revelation about his signing the surveillance application.

Former Milwaukee County sheriff David A. Clarke Jr., a prominent Trump supporter who has advised a pro-Trump super PAC and was considered for an administration post, linked to that report on Twitter on Tuesday and commented, “Evidence that moving a few deck chairs around won’t fix what ails the FBI. We must FIRST find out the depth of the corruption. How far did the cancer spread? THEN start the purge. If we miss this important step, the illegal behavior will continue.”

Before Trump was elected, Boente had been working as the U.S. attorney in the Eastern District of Virginia — one of the premier federal jurisdictions in the country, known for its handling of high-profile terrorism and public corruption cases. Prosecutors under Boente were intimately involved in the investigation into Clinton’s use of a private email server while she was secretary of state, and they recommended Clinton not face charges in the case, people familiar with the matter said.

A more than 30-year veteran of the Justice Department, Boente was appointed to the U.S. attorney’s job by Obama, and he expected he would depart eventually after Trump made his own picks for those jobs.

Instead, Boente found himself serving as the acting attorney general after Trump fired acting attorney general Sally Yates for her refusal to defend his entry ban. He held that spot until Sessions was confirmed by the Senate, then took over as the acting deputy attorney general before Rosenstein was put in place. He signed the warrant application on Page in April.

When Trump fired 46 other Obama-era holdovers from their U.S. attorney jobs in March, Boente was the one to call them and break the news. Boente, though, kept his U.S. attorney job and recently had also been working as the acting head of the National Security Division and as the U.S. attorney in the Eastern District of Virginia.

Though he was eventually asked to leave the latter post, the White House considered him for other jobs, and he was allowed to stay on until a successor was in place. In recent weeks, FBI Director Christopher A. Wray picked him to be the bureau’s general counsel, and he resigned from his post in the Eastern District of Virginia.