Updated Jan 21, 2022 - Politics & Policy

Scoop: Trump’s friends worry legal pick for N.Y. case lacks experience

Illustration of President Trump with a giant gavel over his head

Photo illustration: Sarah Grillo/Axios. Photo: Brandon Bell/Getty Images

Close associates and advisers to Donald Trump tell Axios they're concerned by his decision to use a relatively inexperienced New Jersey attorney, Alina Habba, in his high-stakes legal fight against New York Attorney General Letitia James.

Why it matters: A former president typically has access to the country's most prestigious experts, including lawyers. Trump has turned to the former general counsel for a parking garage company, who works from a small law office near his Bedminster, N.J., country club.

What they're saying: "He has some lawyers that are very sophisticated with years of experience litigating, and he has now fallen prey to inexperienced lawyers who are just telling him what he wants to hear," said one source close to the former president.

Like others, the source requested anonymity to discuss sensitive matters.

  • "It's disconcerting to everyone around him who actually care about him," the source said.
  • A second source, who's close to the Trump legal team, told Axios: "There are real concerns about having a state court tort lawyer come in to represent Donald Trump, not understanding the nuances and issues that surround a former president."

Habba responded in a statement to Axios: "It is a sad day when the press finds the need to belittle someone who has elected not to work at a 'white shoe' firm but has rather opted to build and manage her own law firm."

  • "If you believe former President Donald Trump has fallen prey and is being victimized by someone such as myself, then you do not understand Donald Trump, the Trump Organization or his family very well."
  • Eric Trump, a son of the former president and executive vice president of the Trump Organization, also defended Habba.
  • In a statement to Axios, he described her as "an incredibly competent attorney" who has "our utmost trust and confidence and has the fortitude to take on some of the most politically corrupt and unethical institutions in this country."

The details: Habba, 37, began representing Trump last year. She frequents Bedminster, which is how she and the former president got to know each other, according to a source familiar with the club's membership.

  • Over the past six months, Habba has represented Trump in a lawsuit against his niece Mary Trump and The New York Times.
  • She's also represented him against defamation claims from two women who allege Trump sexually assaulted them.

Between the lines: Habba has taken on jobs that Trump advisers say might be rejected out of hand by most high-profile attorneys.

  • Trump routinely pushes his lawyers to file lawsuits many legal experts find frivolous. But lawyers who bring frivolous claims risk problems for themselves, including being sanctioned by courts or losing credibility with judges whom they might encounter for other cases.
  • High-profile lawyers tend to care deeply about whether they win in court — or at least whether they can win in court. Trump, on the other hand, routinely issues threats and files lawsuits that seem designed for publicity rather than legal success.
  • He seeks out lawyers who'll accede to this approach, an adviser to the former president told Axios.

On Nov. 15, for example, Habba sent a "demand letter" to the interim administrator of The Pulitzer Prizes.

The big picture: On Dec. 20, Habba took another legal action on Trump's behalf — filing a lawsuit against James, the New York attorney general.

Habba tried to stop her civil investigation into his business and block James from participating in a separate criminal investigation.

  • Habba then launched a media barrage, publicly attacking James as too biased against Trump to do her job. (James has a history of calling Trump an "illegitimate president," and saying she looked forward to suing him when she became attorney general.)
  • In appearances on the pro-Trump TV network Newsmax, Habba described James as a "sick person," "unhinged" and "incredibly obsessed" with Trump. She also suggested the state's top law enforcement officer may soon have "a bunny boiling in a pot."
  • James appeared undeterred. On Tuesday, she filed a motion "to compel Donald J. Trump, Donald Trump Jr. and Ivanka Trump to appear for sworn testimony as part of the office's ongoing civil investigation into the Trump Organization's financial dealings."

Yes, but: One of Washington's top white-collar lawyers, William Burck, said Habba's lawsuit to block James' investigation was "a huge stretch."

He said it had little hope of success because courts are loath to interfere with investigations by prosecutors.

  • Still, Burck said, James' unusually aggressive public statements about Trump could later create problems in court, if he's charged as a result of the criminal investigation of Trump in which James is also participating.
  • "This is why prosecutors avoid bad-mouthing potential defendants in public before they are charged," Burck said, "because it undermines their right to a fair trial and pollutes the jury.
  • "Prosecutors are supposed to be above politics and just about the facts. When they sound more like politicians, they can get in real trouble with judges."
  • A James spokesperson said in a statement: "Every investigation that Attorney General James pursues is guided solely by the facts, and she follows those facts wherever they lead. The facts outlined in the court papers filed this week speak for themselves."

Don't forget: When Trump doesn't like what he's hearing from the more experienced attorneys in his orbit, he often disparages them to their faces.

He also turns to other lawyers who'll tell him what he wants to hear and be willing to perform for him on his favored cable outlets: Fox, OAN and Newsmax.

  • That's been true whether they've been his former White House counsels or outside attorneys, according to sources who've witnessed these exchanges between Trump and his attorneys.
  • This trend reached its zenith during the final days of Trump's presidency, as he sought to overturn the 2020 election.
  • He rejected the advice of his White House and campaign lawyers and turned to Rudy Giuliani, Sidney Powell and Jenna Ellis.
  • They all failed repeatedly in their legal efforts and spouted baseless conspiracy theories. Giuliani and Powell now face their own legal action as a result of some claims.
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