Being Trump’s Lawyer Is Dangerous. Here’s Why.

The list of Donald Trump lawyers now facing their own legal difficulties is long and growing.
Donald Trump greets Rudy Giuliani at the clubhouse at Trump National Golf Club Bedminster in Bedminster Township, N.J. on Sunday, Nov. 20, 2016.

Former President Donald Trump has a lawyer problem. And that’s a risky place to be for a guy facing multiple criminal investigations. 

Recent courtroom maneuvers by Trump’s attorneys in the spiraling Mar-a-Lago investigation have been so erratic they’ve prompted public mockery from the legal community at large.


Trump’s team has filed inexplicably late motions, raised incoherent arguments, made bumbling technical errors, and prompted one judge to ask, in writing, what they were talking about. Two Trump lawyers are now widely believed to have inadvertently made themselves witnesses in the investigation, if not targets, by handing the Department of Justice written assurance that they couldn’t find any more documents marked classified at Trump’s country club shortly before an FBI search found dozens.

“Their legal briefs aren’t even well-written,” said Nick Ackerman, a former member of the prosecution team in the Watergate scandal of the 1970s. “They’re contradictory. They’re a joke. There was one paper I had to read five or six times just to figure out what they were saying. It was really that bad.”


Yet perhaps there should be little mystery why Trump has struggled to add heavy-hitters to his legal lineup: His attorneys have a long history of catching legal problems of their own. 

Trump’s previous lawyers have racked up such an impressive run of their own criminal investigations and charges, and even billion-dollar lawsuits, that legal circles have begun to wisecrack that Trump’s MAGA motto really stands for “Make Attorneys Get Attorneys.” 

The trouble faced by the attorneys defending Trump’s interests in the Mar-a-Lago scandal is only the latest chapter in a saga stretching back years. 

It’s worth remembering this epic series of legal jams at a moment when Trump is perhaps more in need of good professional legal advice than at any other time in his tumultuous career. A federal grand jury is probing Trump’s handling of sensitive government documents, and an aggressive prosecutor in Atlanta, GA, is zeroing in on Trump and his allies’ attempts to flip his 2020 election defeat in the peach state into a win. 

With Trump’s future in the balance, here’s a non-exhaustive list of the mind-boggling trouble his attorneys have already stepped in. 

Evan Corcoran and Christina Bobb

In August, the Department of Justice detailed in a court filing how two Trump attorneys, Evan Corcoran and Christina Bobb, may have misinformed government attorneys about whether, and where, sensitive government documents were being held at Trump’s Mar-a-Lago club. 

While it’s far from certain that they will be charged, the pair will likely have to answer questions about what happened, lawyers said. 


Since that revelation, Bobb has kept her distance from the legal battle with the Department of Justice. She recently retained a lawyer, the New York Times has reported, a person familiar with the situation

Corcoran has continued adding his name to legal briefs, but hasn’t piped up during the hearings. 

One recent unconfirmed report, however, suggests they may soon have some hard choices to make. 

The Department of Justice may soon put both of them in front of a grand jury to field inquiries about their activities and interactions with Trump, David Rohde, executive editor for the New Yorker, claimed on MSNBC on Sunday morning, citing unnamed sources.

“I think they're gonna put them before the grand jury, Corcoran and Bobb, and get them to answer questions under oath,” Rohde said. “They will either implicate Donald Trump, saying ‘Donald Trump told me all the classified documents have been turned over,’ when they had not. And if they lie, they will have implicated themselves in a crime.”


Rohde said: “These prosecutors are very good at this. The FBI is very good at it. And they're going to try to flip witnesses. The key thing that you are talking about is the jeopardy that his lawyers in the Mar-a-Lago case face.”

Michael Cohen

Michael Cohen was the OG Trump ultra-loyalist lawyer who ended up with criminal problems for his efforts. 

Cohen served for years as Trump’s private attorney before pleading guilty to criminal charges in 2018 and receiving a three-year sentence for tax evasion and other crimes. After his ordeal, Cohen said he thinks Bobb and Corcoran should step away from Trump as quickly as they can. 

“The smartest thing Corcoran and Bobb could do at this time would be to distance themselves from Trump,” Cohen told VICE News. “The longer they remain associated to the former president, the more they will become entrenched in his lies and illegalities.” 

Cohen has long insisted that any Trump underling who expects protection or loyalty doesn’t appreciate how quickly Trump could turn on them. Trump will throw them under the bus if he believes that will save himself, Cohen predicted. 

“Donald will do what he always does: apply blame to them,” Cohen said.


Rudy Giuliani

Rudy Giuliani, the former mayor of New York City, reinvented himself as Trump’s personal lawyer with wild TV appearances. That included hosting one of the most infamously weird press conferences in U.S. history at Four Seasons Total Landscaping in Philadelphia, where Giuliani gathered reporters in a parking lot to insist Trump won the 2020 election (he didn’t).  

But Giuliani’s in trouble in Georgia, where he’s been formally told he’s a criminal target in the Manhattan District Attorney’s spiraling investigation into the Trump team’s efforts to reverse Trump’s 2020 defeat. 

That means Giuliani is very likely to be charged, lawyers following the case have said. 

Giuliani licenses to practice law in New York and Washington DC were suspended last summer, largely over his attempts to help Trump reverse his 2020 election defeat. 

In August, Giuliani’s ex-wife Judith, asked a judge to consider jailing him for contempt of court if he didn’t swiftly pay $262,000 she said he owed her under the terms of their divorce settlement.


Giuliani has also been under investigation by federal prosecutors in Manhattan for months over potential foreign lobbying violations. But the New York Times reported in August that he’s unlikely to be ultimately charged in that case.   

John Eastman

John Eastman, the conservative lawyer who helped develop a strategy for Trump to cling on to power after losing the 2020 election, may also be in hot water in Georgia. 

Eastman’s own lawyers told the New York Times that he is “probably a target” in the same Georgia probe that’s now targeting Giuliani. 

Eastman appeared remotely with Giuliani at a hearing held by a Georgia State Senate panel in December 2020, where he insisted that President Joe Biden’s victory in the state should not be certified due to what he claimed were irregularities. 

Unlike Giuliani, Eastman hasn’t been officially informed that he’s a target of Fulton County District Attorney Fani Willis’ criminal probe of the Trump team’s attempts to flip the result, Eastman’s attorney, Harvey Silverglate, told the Times


Silverglate told the paper he believed Eastman hadn’t broken any laws in Georgia. 

“I don’t think my client is going to be convicted of anything,” Silverglate said. “If he is indicted, a motion to dismiss will end the case.”

Eastman appeared before a special grand jury probing potential election interference, and was advised by his attorneys to assert attorney client privilege and the constitutional right to remain silent where appropriate.”

Sidney Powell

Sidney Powell, the pro-Trump lawyer known for her failed “kraken” lawsuits, is being sued for billions by voting technology firms Smartmatic and Dominion. 

She surged to prominence in Magaworld after the 2020 election with incendiary and baseless public statements assailing the integrity of the results, and by filing a series of lawsuits in four states that she promised would “release the Kraken” and validate her claims. 

All her Kraken lawsuits were defeated

Now, the voting companies accuse Powell—along with Giuliani and conservative news networks Fox News, OAN and Newsmax—of making false claims about their roles in the 2020 election. 

Dominion filed a 124-page, $1.3 billion lawsuit against Powell in January 2021 which stated: “Powell falsely claimed that Dominion had rigged the election, that Dominion was created in Venezuela to rig elections for Hugo Chávez, and that Dominion bribed Georgia officials for a no-bid contract.”


Powell is also fighting to hold on to her law license in Texas with the state bar’s disciplinary arm, which called her election lawsuits “frivolous.” Powell has called that ethics case “baseless.” 

Pat Cippolone

Former White House counsel Pat Cippolone hasn’t been accused of any criminal wrongdoing. But he’s had to testify—a lot.

Cippolone has found himself at the center of the Congressional investigations into the Jan. 6 insurrection, where he gave damning testimony about other members of Trump’s inner circle. 

Cippolone recalled one contentious, late-night meeting in which Trump allies, including Powell and former National Security Advisor Michael Flynn, discussed seizing voting machines. 

“That’s a terrible idea for the country. That’s not how we do things in the United States. There’s no legal authority to do that,” Cippolone said. 

Chippolone also received a subpoena to testify before a federal grand jury in Washington D.C. investigating events surrounding Jan. 6 in early August. He followed up with a four-hour appearance on Sept. 2. 

Ty Cobb

Ty Cobb, who defended Trump during the Mueller investigation into Trump’s ties to Russia, isn’t in trouble. But he’s come out blasting Trump. 

It’s an extremely rare turn for an attorney to take against a former client. 

Cobb said Trump’s lies about fraud in the 2020 election should be “disqualifying” for the former president to run again. 

“The Big Lie, and the related violence, election interference and other perceived misconduct, was and is an affront to this nation and its first principles,” Cobb told NBC. “It has permanently soiled the history pages and deepened the abyss that divides our country and continues to expand due to the delusions and lack of accountability of politicians in both parties.”

Cobb continued: “It should be disqualifying for Trump and his political acolytes, and would have been at any other time in our history.”

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