Kurt Olsen Helped Trump Fight His 2020 Defeat. Trump Is Talking to Him Again.

Kurt Olsen Helped Trump Fight His 2020 Defeat. Trump Is Talking to Him Again.

Mr. Olsen, a lawyer, has spoken to the former president multiple times in recent weeks. He’s insisted it’s important to make legal demands concerning voting-machine data before Election Day.

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By Maggie HabermanJonathan Swan and Nick Corasaniti

A lawyer who tried to help Donald J. Trump overturn his 2020 presidential election loss has been in direct contact with Mr. Trump once again as his allies start to lay the groundwork for challenging this year’s election results in key battleground states, according to two people with knowledge of their discussions.

The lawyer, Kurt Olsen, has spoken to Mr. Trump multiple times in recent weeks, the people said. In 2021, Mr. Olsen spoke to Mr. Trump several times by phone on the day of the Jan. 6 attack on the Capitol by a pro-Trump mob, and a federal judge later imposed sanctions on him for filing baseless claims about the midterm elections in Arizona in 2022.

Mr. Olsen has insisted to Mr. Trump that it’s important to make legal demands before Election Day related to the preservation of data from voting machines in Arizona, Wisconsin and Georgia, according to one of the people with knowledge of the discussions.

The former president is said to have been generally encouraging of Mr. Olsen. Others in Mr. Trump’s orbit view the continuing demands by lawyers like Mr. Olsen about the voting machines as potentially detrimental to any valid legal efforts Republicans might file should there be contested elections in the battleground states. Those Republicans believe judges will view such demands as frivolous.

Mr. Olsen did not immediately respond to multiple requests for comment. A Trump campaign spokesman did not respond to an email seeking comment.

In late 2020, Mr. Olsen, a lawyer based in Washington, D.C., got to know Mr. Trump as the former president listened to almost anyone offering to help him stay in power. Back then, Mr. Olsen was a little-known lawyer with a history of defending companies in product liability cases. He had joined the Texas attorney general’s failed effort to persuade the Supreme Court to stop four battleground states from certifying Joseph R. Biden Jr.’s victory over Mr. Trump.

When that case failed, Mr. Olsen helped draft a civil complaint based on the Texas lawsuit. He tried to bring the complaint in front of the acting U.S. attorney general, Jeffrey A. Rosen. At one point, Mr. Olsen wrote that “the President directed me to meet with AG Rosen today to discuss a similar action to be brought by the United States,” according to emails obtained by the House Oversight Committee.

Unable to reach Mr. Rosen, Mr. Olsen drove to the attorney general’s office “in the hopes of meeting” with him face-to-face. When officials from the Department of Justice initially reviewed the complaint, they found it to be flawed and noted that it did not seem “viable,” according to documents from the House committee that investigated Jan. 6.

Mr. Olsen was not deterred. Two years after the Jan. 6 riot, Mr. Olsen represented Kari Lake, the former news anchor and outspoken Trump ally, in her unsuccessful legal battle to reverse her loss to Katie Hobbs in the 2022 Arizona governor’s race. Ms. Lake is now the Republican Senate candidate in Arizona.

Even in Mr. Trump’s world, Mr. Olsen is viewed as something of a fringe figure. But Mr. Trump has shown little interest in verifying claims or even reviewing them in detail. His approach to election litigation has been the legal equivalent of throwing spaghetti at the wall, believing it is better to try even the least supported and most provocative legal theories.

As Election Day grows closer, Mr. Trump has been directly in touch with activists who are sympathetic to his claims of election fraud in a handful of the key battleground states, according to a person with knowledge of the discussions.

One of his persistent questions is whether his lawyers are doing a good enough job of “stopping the steal,” according to people with knowledge of the private conversations. Mr. Trump has told his advisers repeatedly they don’t need to worry about turning out voters. He has told them that he will take care of drawing people to the polls, and that what they need to focus on instead is “stopping Democrats from cheating.”

Mr. Trump’s claims about the 2020 election are baseless, and his lawyers have failed decisively in their efforts to prove his claims in court.

At Mr. Trump’s behest, the Republican National Committee has transformed from what has historically been a voter mobilization operation to a so-called election integrity enterprise. Mr. Trump selected the new R.N.C. chairman, Michael Whatley, because he was convinced that Mr. Whatley had prevented Democrats from cheating in 2020 in Mr. Whatley’s home state of North Carolina, which Mr. Trump narrowly won.

As a result of his 2020 efforts, some of Mr. Trump’s election lawyers have been indicted or had sanctions levied against them, including Rudolph Giuliani, Boris Epshteyn, Jenna Ellis, Sidney Powell and John C. Eastman, among others.

In 2023, Arizona’s Supreme Court imposed sanctions on Mr. Olsen for making an “unequivocally false” representation in his effort to help Ms. Lake overturn the results of the governor’s race. More recently, Mr. Olsen has threatened officials in Maricopa County, Ariz., with legal action unless the county accedes to his demands for specifics about passwords and logs associated with the voting machines.

That effort has been met with a lengthy dismissal by Maricopa County officials, who described the theories that the machines were improperly secured and maintained as baseless.

On Sept. 19, as the 2024 general election was in full swing, Mr. Olsen sent a letter to the Maricopa County attorney that he described as a “Pre-Litigation Demand Letter Regarding Maricopa County’s Non-Compliance With Arizona Election Law.”

The letter, addressed to Rachel Mitchell, the county attorney, and obtained by The New York Times, made sweeping claims that the county was violating Arizona election law and that its voting machines, run by Dominion Voting Systems, were not adequately secured. At issue were encryption keys and passwords for accessing the voter data. Last year, Dominion won a nearly $800 million settlement from Fox News for the network’s promotion of lies that the voting machines had corrupted the 2020 election results in favor of Mr. Biden.

Another attorney based in Arizona, Dennis Wilenchik, sent a similar document to Maricopa County officials on behalf of the county Republican committee on Sept. 28, building on the theories described in Mr. Olsen’s letter. A lawyer at Mr. Wilenchik’s firm sent emails in late 2020 supporting the use of “fake” slates of electors, a scheme for which multiple campaign officials and lawyers were ultimately indicted.

On Oct. 3, Ms. Mitchell sent a 22-page response to Mr. Wilenchik, pointing out that Mr. Olsen had previously had sanctions levied against him for pursuing frivolous lawsuits and leveling false allegations.

Mr. Wilenchik did not respond to a request for comment.

Ms. Mitchell’s letter explained how Mr. Olsen and his election technology “experts” had misunderstood the security systems involved in the Dominion voting machines.

Alain Delaquérière contributed research.