The Shady Side Of Alina Habba

As much as the MAGA following likes to believe that Donald Trump can walk on water politically, that buoyancy hasn't served him very well in the courtroom throughout 2023 and the start of 2024. Besides facing 91 criminal charges at the time of this writing, he's also in a great deal of litigious hot water, and has placed much of the responsibility towards handling the latter in the hands of lawyer Alina Habba. As a founding partner of the Habba Madaio & Associates law firm headquartered in New Jersey, she's included on the Super Lawyers Rising Stars List, and has taken on high-profile cases that included suing a nursing home for such violations as storing 17 frozen bodies of COVID victims and successfully taking on a town council whose employee sexually assaulted several children.

Habba's star rose even further in 2021 after she was hired by Trump, whom she met when frequenting his New Jersey golf club and resort. Despite accusations that her videogenic appearance prompted the appointment, Habba said to the New York Post, " ... just because I'm pretty doesn't mean I'm not a brilliant lawyer." Although she's nowhere near as seasoned as other barristers on the Trump payroll, Habba's kept her nose relatively clean so far, unlike Michael Cohen and Rudy Guiliani, who stepped into legal guano while defending the former president. Currently, the jury's out concerning her track record with Trump, but like her employer, she's become a firebrand prone to committing some rather questionable deeds tainting her brand.

Legal eagles were understandably mystified that Donald Trump added Alina Habba to his litigator lineup in 2021. But those already working for him were more than puzzled; they frequently mocked Habba and questioned her abilities, according to a Daily Beast investigation. "'What the f** is she doing?' is probably the most common question we asked about her," said one lawyer on condition of anonymity. Said one Trump advisor to Axios, "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." 

Habba's portfolio was hardly stellar, having graduated in 2010 from Pennsylvania's Widener School of Law, which U.S. News and World Report ranked at No. 159 out of 196 law schools in the country. And since setting up her private practice, which was incorporated in 2021, she hadn't tried any high-profile cases. 

But once on board the Trump tort train, Habba hit the ground running by defending Trump against a sexual assault suit against him during his days on NBC's "The Apprentice," a case that the plaintiff eventually dropped. She also launched a suit on her employer's behalf against The New York Times for revealing tax evasion information from documents supplied to them by Trump's niece, Mary. The judge dismissed the case and forced Trump to pay nearly $400,000 in damages. Habba's track record with Trump would get even worse.

It wasn't enough for Donald Trump to dance on the bones of Hillary Clinton's dreams of presidency; victory wouldn't be complete without totally eviscerating the corpse. In September 2022, he enlisted Alina Habba to file papers against his Democrat foe on the grounds that allegedly, she, FBI officials, and the party cooked up a Russian interference plot to compromise his electoral campaign. Judge Donald Middlebrooks immediately threw the case out of court, and in January, sanctioned Trump and Habba for nearly $1 million. "Here, we are confronted with a lawsuit that should never have been filed, which was completely frivolous, both factually and legally, and which was brought in bad faith for an improper purpose," he wrote in his assessment, per NPR. He was particularly unkind to Habba. "Mr. Trump's lawyers saw no professional impediment or irony in relying upon Russian intelligence as the good faith basis for their allegation," he wrote per Politico.

Neither Trump nor Habba commented on the ruling, although The Guardian hinted that a bit of backroom bickering had taken place behind closed doors. Apparently, Trump wanted to withdraw the lawsuit after finding out that the presiding judge would be Middlebrooks, who was appointed to his position by Clinton's husband, Bill Clinton, in 1997 when he was president. Habba still wanted to press ahead anyway. After losing the case, one source claimed that Trump wanted Habba's firm to pay the entire amount.

Alina Habba might be a firebrand in the courtroom, but her office behavior was enough to turn off former legal assistant Na'Syia Drayton, who sued her boss for racial harassment and discrimination in July 2022. Drayton had an issue with Habba and law partner Michael Madaio singing along to gangsta rap with heavy emphasis on the n-word, presumably to psych themselves up before heading to court. On another occasion at a staff luncheon, she casually told Drayton, the office's sole black employee, to order chicken because "You people like fried chicken," per Above the Law. After losing a case representing Donald Trump in a civil fraud trial that could see her client give up millions in damages, Habba freaked out about New York Attorney General Letitia James, who filed the charges, once exclaiming, per Daily Beast, "I hate that black b****!"

These incidents made Drayton uncomfortable, believing that Habba was fostering a toxic work environment, which were concerns that she conveyed to her boss via email. Later that night, Drayton received an angry call from Habba, apparently not crazy about the allegations. "I am a f**king minority myself!" reportedly said Habba, who is of Iranian descent. "I'm not white. I used to be bullied because I am Arab. Everybody listens to Kanye West — and, I'm not allowed to?" she added, per Business Insider. The suit was settled out of court, and no compensation for damages was publicly revealed.

One strength Alina Habba possessed in the courtroom was her prowess at cross-examination, where she's been known to tear apart a witness with the ravenous fury of a wolverine shredding a hapless rabbit. Her claws were particularly sharp when taking on former Trump lawyer Michael Cohen, a witness during a civil fraud trial pitting Trump against New York's attorney general Letitia James. Habba struck a major artery after getting Cohen to admit that he had previously lied under oath, when the judge asked if she needed a break. "Your Honor, if it's entertaining, I'm happy to go all night," she responded, per ABC News.

But that hostile offense didn't work out for Habba while questioning E. Jean Carroll, who won a previous trial that found Trump guilty of sexually abusing and defaming her. In a follow-up Carroll civil trial, this time over the issue of other instances of defamation, Habba pushed the witness on old social media entries she felt were pertinent. Habba frequently argued with Judge Kaplan, who sustained several objections to her tactic. Habba was also rebuked by the judge when she asked Carroll if media appearances she made after her trial victory were on "left-leaning platforms," per Inner City Press on X. But Kaplan was especially upset about one cross-examination when Habba began reading from a document that had not been entered into evidence. "Now look, Ms. Habba," Kaplan said, per CNN. "We're going to do it my way in this courtroom, and that's all there is to it."

Whether Donald Trump, facing 91 criminal charges, winds up in the slammer is still up in the air. But on the civil law side, his barrister, Alina Habba, almost wound up cooling her heels in the big house. On Jan. 26, the day that the jury was to deliberate on the defamation trial involving Donald Trump and E. Jean Carroll, Habba argued with Judge Lewis Kaplan about a slide she wanted to display. The slide was a series of tweets denying a connection between Carroll's declaration of hardships of being sexually assaulted by Trump and any libelous social media comments made by the former president. Habba argued that some Carroll remarks were made before Trump's allegedly defamatory declarations, which she hoped would prove no direct link existed between the two series of posts. After Kaplan turned down Habba's proposal, since the slide wasn't previously admitted as evidence, Habba objected to the ruling, which irritated the judge. "You are on the verge of spending some time in the lockup," Kaplan angrily responded, per Salon. "Now, sit down."

Later on a cable news channel, Habba demonstrated how livid she was because of the judge's handling of the dispute. "If that is the point we are at as a country, where we literally have to suffer from this Trump Derangement syndrome, really, that it was, it was like being in an epic 'Twilight Zone,' where no rules were allowed, but for the other side." she said on Newsmax.