Kenneth Chesebro

Kenneth John Chesebro (born June 5, 1961 is an American attorney known as the architect of the Trump fake electors plot that conspired to overturn the 2020 U.S. presidential election.

On August 14, 2023, Chesebro was indicted along with eighteen others in the Georgia election racketeering prosecution. On October 20, he pleaded guilty to one felony count of conspiracy to commit filing false documents. As part of his plea bargain, Chesebro accepted five years of probation, $5,000 in restitution, 100 hours of community service, and agreed to testify against Donald Trump and the remaining defendants.

Early life and education
Kenneth Chesebro was born in 1961 and raised in Wisconsin Rapids, about 100 miles north of Madison, Wisconsin. His father was a music teacher and his mother was a speech therapist.

Chesebro earned a Bachelor of Science from Northwestern University in 1983. He earned a Juris Doctor from Harvard Law School in the class of 1986 that included Supreme Court Justice Elena Kagan and Jeffrey Toobin. During law school, Chesebro, Kagan, and Ron Klain were research assistants for Harvard Law School professor Laurence Tribe.

Legal career
After law school, Chesebro clerked for Judge Gerhard Gesell in Washington, D.C. Gesell was known as a liberal jurist who presided over high-profile cases including the Nixon administration's case involving the Pentagon papers, where he ruled in favor of the Washington Post.

In 1987, Chesebro opened his own law firm in Cambridge, Massachusetts. For at least the next 13 years he continued to do occasional work with Laurence Tribe, including working on Bush v. Gore in support of Vice President Gore. In 2023, Tribe said that Chesebro was "obviously bright and seemingly decent." Tribe also stated that "even though we used to be friends, I really think he should never again be allowed to practice law."

Starting in 2016, Chesebro's legal work began to support conservative causes and prominent Republicans. That year, along with John Eastman, he filed an amicus brief with the Supreme Court in a case involving citizenship of residents of American Samoa. In 2018, he represented Republican politicians, including Ted Cruz and Mike Lee, in a Utah voting rights case.

Political affiliation
Until 2016, Chesebro was a registered Democrat. He changed his registration in Massachusetts to unaffiliated. A few years later he moved to New York where he also registered as unaffiliated.

Chesebro skewered the "Reagan Administration ideologues and their colleagues in Congress" in a 1993 article in the American University Law Review. Later in the 1990s, he donated to Bill Clinton. In 2000 Chesebro donated to John Kerry's senate campaign. In 2004, he was an enthusiastic fan of Barack Obama, after Obama's convention speech that year. He also donated to Wisconsin Democratic Senator Russ Feingold.

In 2016, Chesebro began supporting Republicans, with contributions to J. D. Vance, Ron Johnson, and others. Senator Johnson had arrived in the Senate after defeating Feingold in Chesebro's native state of Wisconsin. In 2020, Chesebro donated $2,800 to the Trump campaign.

Chesebro has donated more than $50,000 to Republicans.

Legal work related to the 2020 presidential election
Working as an outside advisor, Chesebro wrote three memos to Jim Troupis, a former Wisconsin judge and a lawyer with the Trump campaign. The first memo is dated November 18, the second is dated December 6, and the third is dated December 9, 2020. The three memos outlined a plan to give the 2020 election to Donald Trump.

Focused on challenging the Wisconsin vote, Chesebro argued in the November 18 memo that "the Presidential election timetable affords ample time for judicial proceedings." He asserted that January 6 was the only deadline that mattered for settling a state's electoral votes and used the 1960 Hawaii election as an example of a competing slate of electors.

The New York Times first revealed the November 18 and December 9, 2020, memos on February 2, 2022. The December 6, 2020, memo was not made public until Trump's federal indictment in the 2020 election interference case on August 1, 2023. The Times called the December 6 memo "a missing piece in the public record of how Mr. Trump’s allies developed their strategy" to overturn the election.

The strategy was to have Trump-Pence electors in six allegedly contested states submit alternate slates of electors in hopes that Pence would count them. The December 6 memo expanded Chesebro's scope beyond Wisconsin into a national strategy. In it Chesebro said he believed the strategy was "constitutionally defensible" but acknowledged that the Supreme Court might rule against it and said he was "not necessarily advising" it. Nevertheless, the memo was written with a sense of urgency to act. The main topic of the December 6 memo was "Important That All Trump-Pence Electors Vote on December 14." Chesebro concluded the memo saying "Given the possible upside of having the Trump-Pence electors meet to vote on December 14, it seems advisable for the campaign to seriously consider this course of action and, if adopted, to carefully plan related messaging."

Chesebro's objectives were to focus the public's attention on alleged "electoral abuses by the Democrats" and to "buy the Trump campaign more time to win litigation that would deprive Biden of electoral votes and/or add to Trump's column".

The memos ultimately inspired the scheme in seven states, though Vice President Mike Pence did not accept the Trump-Pence electors and refused to participate in the scheme. Laurence Tribe, Chesebro's former mentor, would later join an ethics complaint filed with the New York Bar regarding the December 6 memo. In an article for Just Security, Tribe complained: "Chesebro completely misused part of the latest edition of my constitutional law treatise."

On December 13, 2020, Chesebro emailed Rudy Giuliani and others with a proposal for Pence to recuse himself from certifying the election results. He argued that a vice president who has just run for re-election has a conflict of interest, and he suggested that instead Chuck Grassley or another senior senate Republican should assume the role of certification. In this proposed strategy, when the senator opened the Arizona envelopes and found two conflicting elector slates, he would halt the certification and suggest that Arizona's Republican-controlled state legislature appoint electors instead. Grassley told Roll Call on January 5 that "We don't expect [Pence] to be there", though Grassley's office quickly walked back the statement and claimed that neither he nor his staff had been aware of the proposal. On March 28, 2022, Judge David O. Carter, after considering Chesebro's email during a court case, ruled: "President Trump's team transformed a legal interpretation of the Electoral Count Act into a day-by-day plan of action. The draft memo pushed a strategy that knowingly violated the Electoral Count Act".

The U.S. House select committee on the January 6 attack concluded that Chesebro had sent the December 13 memo "upon request from Trump Campaign official Boris Epshteyn." Further: Chesebro laid out a “‘President of the Senate’ strategy,” arguing that the “President of the Senate” (“he, and he alone”) is charged with “making judgments about what to do if there are conflicting votes.” Chesebro argued that when the joint session met on January 6th, the President of the Senate should not count Arizona’s electoral college votes for former Vice President Biden, “[b]ecause there are two slates of votes.” Of course, there were not two legitimate “slates of votes” from Arizona. There were the official electors, certified by the State, and a group of fake electors convened by the Trump campaign. Chesebro’s memo set President Trump’s pressure campaign on a course to target the Vice President on January 6. Judge Carter found that the “draft memo pushed a strategy that knowingly violated the Electoral Count Act” and “is both intimately related to and clearly advanced the plan to obstruct the Joint Session of Congress on January 6, 2021.” That plan was also advanced by John Eastman. On December 23, 2020, Trump campaign attorney John Eastman emailed Boris Epshteyn an attachment called "PRIVILEGED AND CONFIDENTIAL — Dec. 23 memo on Jan. 6 scenario." Eastman commented: "I'm fine with all of Ken [Chesebro]'s edits."

On December 30, 2020, Chesebro emailed Eastman and others, saying he planned to stay at the Trump International Hotel in Washington, DC from January 3–8. The next day, Chesebro emailed Eastman and others, suggesting that U.S. Supreme Court Justice Clarence Thomas might be willing to rule that the Georgia count was in "doubt", and that such a ruling might be "good enough" for Pence and Congress to delay their consideration of Georgia's electors on January 6.

On January 6, 2021, the day of the attack on the Capitol, Chesebro was on the Capitol grounds following Alex Jones. It is not known why Chesebro was there, or whether he entered the Capitol building that day.

Chesebro told Talking Points Memo in a June 2022 interview that his actions for the Trump campaign were "what lawyers do."

In February 2024, CNN reported that Chesebro had concealed a secret Twitter account, BadgerPundit, from Michigan prosecutors. Under the account, Chesebro promoted a far more aggressive strategy to overturn the election than he had let on in his Michigan interview.

U.S. House investigation
On March 1, 2022, Chesebro was subpoenaed by the United States House Select Committee on the January 6 Attack. He fought the subpoena but testified on October 26. When asked where he was the first week of January 2021 and specifically on January 6, Chesebro invoked his Fifth Amendment right to remain silent. This committee concluded that he was the chief architect of the fake electors scheme used by Trump and his allies in an attempt to stay in power after losing the 2020 presidential election.

Georgia prosecution
In July 2022, he was subpoenaed by a grand jury in relation to the 2020 Georgia election investigation.

On August 14, 2023, Chesebro was indicted along with 18 other people in the prosecution related to the 2020 election in Georgia. He exercised his right to demand a speedy trial, and his trial was set for October 23, 2023. On September 1, he pleaded not guilty to seven criminal charges, including a violation of Georgia's RICO act and conspiracy to commit forgery, in the Georgia election subversion case, and he also waived his right to an arraignment hearing.

On September 21, his lawyers asked for five pieces of communication — including an email mentioned in the indictment as having been sent by Chesebro to Eastman on January 4, 2021 — to be excluded from evidence. They argued that the documents were protected by attorney-client privilege. On October 10, Fulton County District Attorney Fani Willis argued that attorney-client privilege should not apply because the documents did not advise Trump on litigation but rather gave him a political strategy to use in Congress to interrupt the transfer of power to Biden. In this argument, she echoed prior rulings of U.S. District Judge David Carter.

On October 20, as jury selection began for his speedy trial, Chesebro took a last-minute plea deal, including a single felony count of conspiracy to file false documents. He was sentenced to five years of probation and to pay $5000 in restitution.

Wisconsin prosecution
On June 4, 2024, Chesebro was indicted along with two others in the Wisconsin prosecution of fake electors. He was charged with a single count of conspiracy to utter forged official documents as legitimate.

Role in federal prosecution of 2020 election
On August 1, 2023, Trump was indicted in the federal prosecution for his attempts to overturn the 2020 election. Chesebro has been identified as Co-Conspirator 5.

Involvement in Arizona prosecution
Chesebro was interviewed by Arizona Attorney General Kris Mayes during her investigation into the fake electors plot. Prosecutors questioned Chesebro about a meeting he had with Trump in the Oval Office in December 2020; Chesebro told them he had explained to Trump how his alternate electors could help them to win Arizona. During the Arizona prosecution of fake electors in 2024, Chesebro was referred to in the indictment as unindicted co-conspirator 4.

Career after January 6, 2021
Napoli Shkolnik, a New York-based personal injury firm, hired Chesebro in October 2022 to lead their Law and Motions Department. He moved from New York to Puerto Rico, where other attorneys for the firm live. He was released by the firm after being criminally charged for his part in the attempt to overturn the 2020 election.

Personal life
In 1994, Chesebro married Emily Stevens, a physician. They divorced in 2016.

Chesebro was an early bitcoin investor, netting several million dollars from a 2014 investment. Some former colleagues suggest this newfound wealth triggered his dramatic life-style change; he began to travel extensively, bought houses, divorced, and started donating to Republicans.