The involvement of a person like Olson, who now represents conspiracy theorist and MyPillow CEO Mike Lindell, underscores how the system that would normally insulate a president from rogue actors operating outside of official channels had broken down within weeks after the 2020 election.
That left Trump in direct contact with people who promoted conspiracy theories or questionable legal ideas, telling him not only what he wanted to hear but also that they — not the public servants advising him — were the only ones he could trust.
"In our long conversation earlier this week, I could hear the shameful and dismissive attitude of the lawyer from White House Counsel's Office toward you personally — but more importantly toward the Office of the President of the United States itself," Olson wrote to Trump. "This is unacceptable."
It was not immediately clear how Olson, who practices law in Washington, DC, and Virginia, arrived in Trump's orbit. Olson previously worked with Republican super political action committees and promoted a conspiracy theory that Vice President Kamala Harris is not eligible to be vice president, falsely claiming she is not a natural-born US citizen. He and his firm have long represented Gun Owners of America, an advocacy group.
According to his website, which displays a photograph of him shaking hands with President Richard Nixon, Olson was a White House intern in 1971.
His 2020 memo was written 10 days after one of the most dramatic meetings ever held in the Trump White House, during which three of the president's White House advisers vied — at one point almost physically — with outside actors to influence Trump. In that meeting, on December 18, lawyer Sidney Powell and Michael Flynn, the former national security adviser, pushed for Trump to seize voting machines and appoint Powell special counsel to investigate wild and groundless claims of voter fraud, even as White House lawyers fought back.
But the document suggests that even after his aides had won that skirmish in the Oval Office, Trump continued to seek extreme legal advice that ran counter to the recommendations of the Justice Department and the counsel's office.
And the memo indicates that Trump was acting on the outside advice. At one point, it refers to the president urging Olson to contact the acting attorney general about having the Justice Department lend its credibility to Trump's legal efforts to invalidate the election results.
A person familiar with the work of the House committee investigating the Jan. 6 attack on the Capitol said the committee was aware that Olson was in contact with Trump and that it was exploring Olson's role in pushing forward plans to overturn the 2020 election.
Olson did not respond to requests for comment.
A spokesperson for Trump did not respond to a request for comment about the former president's relationship with Olson.
According to his memo, Olson was discussing with Trump the notion that the Justice Department would intercede with the Supreme Court to reverse his electoral defeat.
The court had declined to hear a case that allies of Trump in Texas had brought challenging the election results in Pennsylvania, saying the plaintiffs lacked standing.
Olson told Trump that he believed the Justice Department "will do nothing except continue to run out the clock."
"While time to act was short when we spoke on Christmas Day, time is about to run out," he wrote.
It was unclear which White House lawyer Olson described as dismissive in his memo. At the time, the White House counsel, Pat Cipollone; Patrick Philbin, his deputy; and another lawyer who did not work for the counsel's office, Eric Herschmann, were working in tandem to push back on some of the more outlandish ideas being recommended. Cipollone and Herschmann had taken lead roles during the December 18 White House meeting in countering Powell and Flynn.
"The feeling I had was that not just was he not offering you any options, but that he was there to make certain you did not consider any," Olson wrote, referring to the unnamed White House lawyer. "But you do have options."
Among those whom Olson mentioned as speaking to Trump about the Justice Department getting involved was Mark Martin, the former chief justice of the North Carolina Supreme Court. White House officials believed at the time that Martin was brought in through Mark Meadows, the White House chief of staff.
Olson urged Trump to hire another lawyer, Kurt Olsen, who had worked on the Texas case.
"As I emailed Molly Saturday morning," Olson wrote, referring to Trump's assistant, "we began acting on your question about our team revising the complaint filed by Texas into what could be the first draft of a complaint filed by the United States. The lawyers with whom I have been working took on that task, and we now have a draft that could be presented to you to review, and by you to Mr. Rosen to edit, improve and file."
In his memo, Olson recounted that during their discussions, he had told Trump that he had followed the president's suggestion to call Rosen a few hours earlier requesting that the acting attorney general file a lawsuit to try to block Joe Biden's Electoral College victory.
Trump, based on Olson's memo, was aware that Rosen was slow-walking his request. The suit was never filed; Rosen testified last month before the January 6 committee that doing so was out of the bounds of the law.
A spokesperson for Rosen said that he did not recall speaking with Olson but that it was accurate that the acting attorney general was against filing any lawsuits to interfere with the election results.
At the time of the memo, Trump had decamped to Mar-a-Lago, but Olson encouraged him to return to Washington to fight the election results from his perch in the White House. Trump did so shortly thereafter, working through the holidays on challenging the election results.
"I do not believe you can do what is required to be done from Florida," Olson wrote to the president. "And, it would send a message about your commitment to the task, to leave Mar-a-Lago to take charge at the White House. I urge you to return as soon as it can be arranged."
Olson also encouraged Trump to fire or reassign Rosen should he not go along with the plans to use the Justice Department to challenge the election in court, though Olson acknowledged such action would draw negative news coverage.
"This step will likely bring on a thousand stories making an analogy to 'Saturday Night Massacre' in 1973 when President Nixon ordered AG Elliot Richardson to fire Archibald Cox as a special counsel investigating Watergate," he wrote.
Olson also urged changes at the White House Counsel's Office. He wrote that a new White House counsel should take steps to ensure a "fair election count," though he conceded that would be seen by the news media as "martial law."
After Trump left office, Olson joined the legal team of Lindell, who has promoted a series of conspiracy theories about the election and has been sued for defamation by a former employee of Dominion Voting Systems. Lindell, who crashed the Oval Office in the final days of the presidency hoping that Trump would still take action related to the election, was adamant that Trump would be reinstated as president in 2021, something that was not possible.
Lindell sued the January 6 committee, seeking to block the panel's subpoena to Verizon for his call logs. The suit, which Olson filed along with other lawyers, argued that Lindell's communications about his objections to the 2020 election were protected speech, in part because they were tied to his religious beliefs.
This article originally appeared in The New York Times.
Written by: Maggie Haberman and Luke Broadwater
Photographs by: Roger Kisby
© 2022 THE NEW YORK TIMES