The critique of the president by Whitaker, a former U.S. attorney who rose to prominence over the past four years as the head of a conservative nonprofit group, has often come in unguarded moments, and sometimes late into on-air discussions. “Sometimes I wonder if anybody has the president’s ear or if he just kind of watches news accounts and responds to, which is a little dangerous,” Whitaker said in June 2017 on a radio show.

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As a media commentator, Whitaker criticized the special counsel’s investigation into Russian interference in the 2016 presidential election. He also lauded Trump, saying he has put the country on the right path, and praised Trump’s media savvy and penchant for keeping his opponents off-balance.

But a Washington Post review of his body of candid and disapproving comments stand out in an administration that demands strict loyalty, with televised Cabinet meetings in which aides take turns glorifying Trump. Whitaker’s assessments were more cutting than anything uttered publicly by Jeff Sessions, the former attorney general whom Trump chased from the job after repeatedly criticizing Sessions for recusing himself from oversight of the special-counsel investigation.

Whitaker, who now holds veto power over some major decisions by special counsel Robert S. Mueller III, declined to comment through a Justice Department spokesman. Trump emerged on Thursday as a major subject of interest in the investigation.

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A person close to Whitaker said the comments show he is more than a mere Trump loyalist. “Matt Whitaker was a conservative legal commentator who called balls and strikes and answered questions about the news of the day,” said the person, who spoke on the condition of anonymity because the person was not authorized to comment on the record. “There are numerous statements and actions by Matt that demonstrate his appreciation and respect for the president’s leadership.”

Whitaker left his job at the nonprofit Foundation for Accountability and Civic Trust (FACT) in the fall of 2017 to take a job as Sessions’s chief of staff.

Six months earlier, Whitaker raised the possibility that Trump might make things up “whole cloth” to suit his political needs of the day, including fabrications that complicate the work of the nation’s top law enforcement officials.

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“I don’t know if it was to throw everybody off the trail or what. But it was a little outlandish, to say the least,” Whitaker said in a radio interview after Trump accused former president Barack Obama of ordering surveillance on his presidential campaign.

“Terrible!” Trump tweeted on March 4, 2017. “Just found out that Obama had my ‘wires tapped’ in Trump Tower just before the victory. Nothing found. This is McCarthyism!”

Two days later, when asked to explain Trump’s claim, Whitaker struggled in an interview aired on WLS, a conservative-talk-radio station in Chicago.

“President Trump will just sort of say these things that puts Comey and others in the law enforcement community and the intelligence community on their heels kind of trying to respond to these, you know, claims whether they’re true or not,” Whitaker said.

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Speaking on the same topic for the radio audience of WIOD in Miami later that day, Whitaker went further, suggesting Trump may have fabricated the idea: “There’s only one of two answers. One is that the new president discovered this information as he assume[d] the position of president or he’s completely made it up whole cloth.”

The White House days later clarified that it concluded that Trump had been caught up in routine surveillance of foreign officials who may have had conversations with the candidate. The Justice Department over the next several months repeatedly rebutted the notion that the Obama White House had ordered surveillance of the Trump campaign.

Whitaker’s criticism of Trump in the White House stretches back to the president’s first week in office. As head of FACT, Whitaker at the time questioned Trump’s sincerity in floating the idea of resurrecting waterboarding and other interrogation tactics.

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“That’s kind of his nature as president: I think he’s going to say bold statements and then see how the people react,” Whitaker said on Chicago’s “Big” John Howell show on WLS. “He’s very adept at adjusting if necessary and suggesting that what he said yesterday is not what he believes today.”

Whitaker was perhaps most critical five months later when, as Trump fired Comey, the president asserted that the FBI director told him he was not under investigation.

In four radio interviews over two days, Whitaker repeatedly blasted Trump’s public letter to Comey as “self-serving.”

“That whole sentence about, you know, ‘We’ve talked three times and you’ve told me I’m not under investigation,’ I mean for a president to include that in a letter of termination is — just I’ve never seen anything like that,” Whitaker told WHO radio in Des Moines. “It’s so self-serving.”

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A day later, Whitaker was still going on “The Steve Gruber Show” on WJIM in Lansing, Mich.: “It was gratuitous. . . . It can’t be confirmed. And so I think in the classic, you know, President Trump fashion, it becomes a fact. He’s very effective at these kind of — you know, these statements that either can’t be verified or you know sort of fly under any way of confirmation,” Whitaker said. “History is going to continue to move forward and I guess, you know, reveal whether these statements are true or false.”

More often, Whitaker defended Trump, especially in appearances on television. But a little over a month before he was named as Sessions’s chief of staff, in September 2017, Whitaker critiqued the president’s response to the clash of white supremacists and counterprotesters in Charlottesville. He described Trump’s comments after the incident as “woefully inadequate” and said that the president could have done more to condemn racist views.

“If white supremacists and alt-right groups are part of his base, he needs to reject that,” he said in a CNN panel discussion.

Eighteen months before he took charge of the Justice Department, Whitaker mused about what a hot seat that could be.

“You have a president that you know is sometimes a little unpredictable, to be generous, and it’s — I don’t know if Jeff Sessions feels comfortable where he’s sitting right now, and he may wish he was back in the Senate.”