Alina Habba's Impossible Job

Alina Habba is facing a difficult job as Donald Trump's attorney, acting on his behalf in a number of high-profile cases.

Habba—appointed the general legal counsel for Trump's Save America political action committee in July last year—has represented the former president in a defamation trial brought by former Elle columnist E. Jean Carroll this week.

A number of the attorney's exchanges with Judge Lewis Kaplan have raised eyebrows among legal experts and commentators.

Former U.S. attorney Joyce Vance said in a Substack post that Habba could be "in over her head."

Some highlighted a clash with Judge Kaplan in which the latter told Habba to "sit down," to which she replied by saying she does not like "to be spoken to in that way."

Others have said Habba's job is made harder in a number of ways, and federal attorney Colleen Kerwick said female lawyers are being held to a higher standard in the public eye.

"I'd rather herald her meteoric growth as an attorney than nitpick at her opportunities for further growth as an attorney and counselor at law," she told Newsweek.

Trump himself has previously described his legal spokesperson as a "warrior" and "great lawyer."

Regardless, Habba's prominence in the Trump legal train—the former president faces civil cases and 91 charges spread across four criminal indictments—could mean she faces another problem, fatigue.

Former Department of Justice (DOJ) litigator Gene Rossi told Newsweek that the high-profile nature of Trump's legal woes could mean Habba has to battle tiredness, a "key enemy" for attorneys when the spotlight is on them

"For 34 years, I have had my share of high-profile jury trials, as a prosecutor and the last six years as a defense counsel," Rossi said. "Fatigue is a key enemy. Big trials are marathons and you need to pace yourself."

She has also been involved in other major cases including Trump's civil fraud trial in which he and his conglomerate were found to have exaggerated the value of his assets, deceiving lenders in the process.

Habba was on Trump's team when a sexual assault case brought by Summer Zervos, a former contestant on The Apprentice, was dropped in 2021.

Rossi added that Trump was an "impossible client" to work with and Vance argued that "good lawyers" won't go near the 45th president because he is "toxic."

Fair or not, Trump has had a high turnover of lawyers, but it is not clear if this has anything to do with the former president or is a legal tactic.

Rossi added: "With respect to Ms. Habba, she has an impossible client, with whom she has to work. Plus, her every move is being analyzed and ridiculed. Add to this Perfect Storm of a disaster is that she does not appear to have a comfort level with the rules of evidence or how to handle a demanding jurist. Other than that, she is doing a wonderful job."

Kaplan denied a number of pre-trial requests from Trump's lawyers. In response, Habba was recorded saying, "I don't know how to try this case, Your Honor."

Habba also faced criticism when legal experts questioned if she had violated a gag order.

Kaplan issued an order that said Trump could not discuss: DNA; funding for litigation; Carroll's previous romantic relationships and sexual experiences; Carrol's choice of counsel and "suggesting or implying" that Trump did not sexually abuse her.

Kaplan wrote that Trump cannot say that Carroll lied about being sexually assaulted and that he did not make statements in 2019 "with actual malice."

On Wednesday, Kaplan threatened to remove Trump from the court after he spoke loudly while Carroll was on the witness stand.

The case brought by Carroll is to determine the damages owed to her after a jury found Trump had defamed and sexually assaulted her.

Trump has denied sexually assaulting her at a Bergdorf Goodman department store in the 1990s in New York. He says he "never met, saw, or touched" Carroll.