‘Brains’ Behind Trump Election Scheme Lying Low in Puerto Rico

Aug 18, 2023
1:06 PM

Rioters loyal to President Donald Trump rally at the U.S. Capitol in Washington, January 6, 2021. (AP Photo/Jose Luis Magana, File)

SAN JUAN — A lawyer accused of crafting former President Donald Trump’s fake elector strategy to overturn the results of the 2020 election, has kept a “low profile” since the attack on the U.S. Capitol on January 6, 2021, having moved to Puerto Rico last year, according to the Washington Post.

Kenneth J. Chesebro, a 62-year-old Harvard-trained appellate lawyer, is one of eight lawyers indicted in Georgia on Monday for allegedly conspiring to overturn the results of the 2020 election. A memo from Trump’s legal team published by the New York Times shows that Chesebro was a key part of the scheme involving fake electors.

In the memo, dated December 6, 2020, Chesebro called on Republican electors in six swing states won by Joe Biden in the 2020 election to cast ballots for Trump and then send them to Washington for the January 6 congressional certification.

The fake elector strategy relied on Trump forcing lawmakers, media and members of the public to “focus on the substantive evidence of illegal election and counting activities in the six contested states,” Chesebro wrote in the memo. Former Vice President Mike Pence would then delay the vote count or block confirmation of the election, which Pence ultimately refused to do.

John Eastman, another lawyer indicted in Georgia, is often credited with being the mastermind of the scheme to halt certification of the Electoral College. However, it was Chesebro who first proposed the idea in a November 18 memo, as reported by Forbes. Chesebro admitted he was “not necessarily advising” the strategy be used and that there were “many reasons” why it might not work.

Chesebro, Eastman and Trump are among the 19 people charged for their alleged role in attempting to overturn the former president’s electoral defeat in 2020. Chesebro faces seven felony charges, including conspiracy to file false documents and commit forgery, as well as racketeering charges.

Eastman faces nine felony charges, while Trump faces 13.

Chesebro was also present at the January 6 attack, according to CNN, though there is no indication that he ever entered the Capitol Building. When previously questioned about his whereabouts during the first week of January 2021 by the January 6th Committee, Chesebro invoked his Fifth Amendment right against self-incrimination.

Laurence Tribe, Chesebro’s former mentor, describes him as the “brains” of the fake elector scheme. “Even though we used to be friends, I really think he should never again be allowed to practice law,” Tribe told Air Mail.

Chesebro has not been charged in the separate federal case brought against Trump, but he has been identified as “co-conspirator 5.” Prosecutors said he designed “a corrupt plan to subvert the federal government function by stopping Biden electors’ votes from being counted and certified.”

Eastman has been identified as “co-conspirator 2” in the federal indictment.

Once a registered Democrat, Chesebro changed his party registration to unaffiliated in 2016, when he also began working with Eastman, affiliated with the right-wing Claremont Institute. He later acted as counsel for Sens. Mike Lee (R-UT) and Ted Cruz (R-TX) in 2018.

Chesebro won several million dollars after betting big in crypto in 2017, which helped spark his conservative turn, Air Mail reported.

In 2020, Chesebro donated the $2,800 maximum to Trump’s presidential campaign and later gave the same amount to Ohio Sen. J.D. Vance (R).

Chesebro moved to Puerto Rico in 2022 while working for Napoli Shkolnik, a New York personal injury firm that has represented victims of the September 11 terrorist attacks as well as victims of the Flint water crisis. Several partners at the firm live in Puerto Rico, COO Gloria Werle told the Washington Post.

Chesebro told House investigators in 2022 that Hurricane Fiona, a Category 1 storm that caused “catastrophic” effects to Puerto Rico and $2.5 billion in damages, delayed the transfer of documents to the January 6th Committee.

Both lawyers handling a case against him in Wisconsin told a judge they had trouble locating Chesebro. Even the House committee has had difficulty finding him, a confidential source told the Washington Post.

Latino Rebels reached out to Chesebro but he did not respond to our request for comment.

According to documents updated in May of this year, Chesebro was not a grantee of Act 60, a tax exemption meant to bring businesses and high-earning individuals to Puerto Rico in exchange for paying little-to-no income taxes.


Carlos Edill Berríos Polanco is the Caribbean correspondent for Latino Rebels, based in San Juan, Puerto Rico. Twitter: @Vaquero2XL