The Most Dangerous Job for Lawyers Is Being on Trump’s Legal Team

Ryan Teague Beckwith
5 min readOct 26, 2023
  • Strategies from civil lawsuits may not fly in criminal cases
  • Five lawyers are unindicted co-conspirators in latest charges
Creative Commons-licensed photo by NCinDC

By Ryan Teague Beckwith
Bloomberg News, Aug. 5, 2023

Donald Trump is learning the hard way that the bare-knuckles tactics he used in civil cases as a businessman can backfire dramatically in a criminal courtroom.

Over decades in business, Trump fought through at least 3,500 lawsuits by making sweeping claims and using his personal wealth to outlast the other side, treating court cases as publicity efforts and his attorneys as “fixers” whose job was to use the law to get what he wanted.

But now he’s in criminal courts, where the same aggressive demands he’s made on civil lawyers aren’t faring as well — especially for his attorneys and the dozens of lawyers in other states who worked unsuccessfully to overturn the election on his behalf.

“That doesn’t work in a criminal setting where he’s not driving things,” said Michael Teter, a Washington lawyer working on state ethics complaints against some of the attorneys who challenged the election results.

Five of Trump’s own former lawyers were identified by people familiar with the case as the unnamed unindicted co-conspirators in the 78-count criminal charging document that special counsel Jack Smith released Tuesday, all pertaining to roles that went well beyond advising Trump on his legal options.

None of them has been charged with a crime.

Despite the legal jeopardy hanging over him, Trump remains the runaway favorite among Republican primary voters for the 2024 nomination and national polls looking ahead to the general election put him in a dead heat with President Joe Biden.

Trump continued to confuse civil and criminal proceedings, referring to the three indictments in a social media post on Friday as “lawsuits.”

Trump has long had associations with controversial lawyers, including most infamously the late Roy Cohn, who advised anti-communist Senator Joe McCarthy and was later disbarred for defrauding a client. But the indictment shows how Trump’s approach to the law can drag down even lawyers with sterling resumes.

John Eastman, who Bloomberg News has identified as co-conspirator №2 in the indictment, once clerked for the US Supreme Court, worked at the white-shoe law firm Kirkland & Ellis, ran for California attorney general and taught constitutional law at Chapman University.

According to the indictment, Eastman personally lobbied the Arizona House speaker and Georgia state lawmakers to decertify Biden’s wins in those states, submitted election fraud claims he knew were false in court filings and drafted a plan to have Vice President Mike Pence throw out Biden electors in Congress, even though he acknowledged that would be against the law and would be rejected by the Supreme Court.

The indictment alleges that a senior White House adviser told Eastman that the plan would lead to “riots in the streets.” He responded, in a rough paraphrase from the indictment, that there had “previously been points in the nation’s history where violence was necessary to protect the republic.”

Even after the Jan. 6 attack on the US Capitol, in which a mob threatened to hang Pence, Eastman emailed the vice president directly at 11:44 p.m., according to the indictment, asking him to “consider one more relatively minor violation” of the law by forcing a 10-day delay in the certification.

Eastman’s defense attorney, Harvey Silverglate, told CNN on Thursday that the email was not asking Pence to break the law but instead simply putting forward “a very minority view” of how to interpret it that “very few people would agree” with.

Pence said he immediately rejected all of Eastman’s proposals as unconstitutional.

“Sadly, the president was surrounded by a group of crackpot lawyers that kept telling him what his itching ears wanted to hear,” he said Wednesday.

The other unnamed co-conspirators have been confirmed to be lawyers already facing personal and professional consequences for their efforts to challenge Trump’s 2020 election losses in key states: former New York City mayor and 2008 GOP presidential candidate Rudy Giuliani, former US Assistant Attorney General Jeff Clark, Sidney Powell and Kenneth Chesebro.

Eastman retired early as a law professor amid protests from his fellow faculty and faces disbarment proceedings in California. Giuliani already had his law license suspended in New York, faces disbarment hearings in Washington and is being sued for defamation by two election workers in Georgia whom he claimed were cheating. Clark, Powell and Chesebro also face ethics complaints.

They are not alone. Some of Trump’s other lawyers have been fined nearly $1 million, lost jobs at high-end law firms, and been sued by their former client. One went to prison and two have even testified against him — an extremely rare move. Another 60 attorneys face unresolved bar complaints over their work on the 2020 election challenges.

Some have been implicated directly in other potential crimes.

An earlier indictment charging Trump with obstruction over his alleged refusal to return classified documents he removed from the White House says that he told one of his lawyers to hide or destroy them after they were subpoenaed, while another lawyer falsely certified to the Justice Department that all the documents had been handed over.

Matthew DePerno, a Michigan lawyer who tried to overturn Trump’s 2020 loss in that state and later ran unsuccessfully for attorney general with his endorsement, was charged this week in connection to a plot to break into voting machines in a failed attempt to prove they had been hacked in the 2020 election.

Silverglate argued that Eastman was simply representing his client. But other legal experts say that being a lawyer does not mean doing everything a client asks.

Diana Florence, a former prosecutor in the Manhattan district attorney’s office, said that there are bright lines lawyers are not supposed to cross, including lying in court or actively trying to undermine the law.

“There’s a difference between defending a crime and being an accomplice,” she said.

© Bloomberg News, 2023

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Ryan Teague Beckwith

National politics reporter. Part-time journalism teacher.