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.

Ever since she was hired by Donald Trump, Alina Habba never seemed fazed about his reputation as a womanizer. And while any rumors that the relationship between Alina Habba and Trump is more than professional remain unsubstantiated, the lawyer makes no bones that her looks certainly helped in landing her famous client. "I don't think I would be on TV or sitting here if I didn't look the way I look," she said on the PBD Podcast. "Somebody said to me, 'Alina would you rather be smart or pretty?' and I said, 'Oh easy, pretty. I can fake being smart.'" She also highlighted her physical features politically by posting a meme from a fan comparing the lawyer to controversial songstress Taylor Swift, a prime target of the far right. The meme displayed photos of the two women, captioned with "Who thinks this country needs a lot more women like Alina Habba, and a lot less like Taylor Swift?" per Meidas Touch Network. 

Trump acknowledged her beauty as well, while praising her legal skills when speaking at a Young Republican gala in New York in 2023. He noted that he was impressed by how Habba would boldly tackle the media when his other lawyers refused. "Alina, she says 'I'll do it, sir, I'll do it,' and she goes and she makes the news every night," he said, per Forbes. "She makes the news every night, screaming at these maniacs."

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.

Besides taking on litigation cases for Donald Trump, she also had a hand in trying to make a problem affecting one of his resorts go away. In 2021, Alice Bianco, an employee at Donald Trump's golf resort in New Jersey, stated that a manager had made sexual advances toward her, even telling her to comply to protect her job. A colleague sent a letter to a Trump's higher-up complaining about how Bianco was treated, which was when Habba entered the picture. Habba approached Bianco, and under the guise of friendship and concern for the employee, urged Bianco to drop the legal counsel she hired. She also persuaded Bianco to sign a non-disclosure agreement, saying it was for her protection.

Realizing she was tricked, Bianco sued the club for violating the New Jersey Law Against Discrimination and wanted to refer Habba and her firm to the Office of Attorney Ethics for ethics violations in 2023. Bianco said via her lawyer, per CNN, "I didn't know my rights. I didn't know Alina wasn't supposed to discuss a case with me without my lawyer. I didn't know New Jersey had banned non-disclosure agreements for victims of sexual harassment. All I knew was that the person claiming to be my friend and advisor threw me in the trash as soon as she pressured me into silence." Responding, Habba said, per Politico, "I always conduct myself ethically and acted no differently in this circumstance."

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.

After getting nailed for a $1-million sanction for trying to sue Hillary Clinton, a case that was thrown out of court in January 2023, Alina Habba gleefully aired that dirty laundry at a conservative convention in Phoenix later that year. "What do you think happened?" she asked an eager crowd at America Fest, per Salon. "Nobody's heard of the case, right? It's 'cause it's gone. I never met the judge. I never walked into the courtroom." Presumably to coax the crowd into believing the legal system was biased against the right, she noted that the case, in which Trump accused Clinton of orchestrating a Russian conspiracy to undermine his otherwise victorious electoral run, involved some 50 leftist lawyers stumping for the Democrat candidate. "It got dismissed, and me and President Trump got sanctioned a million dollars for going against crooked Hillary," she added. "You didn't know that, did you? Fake news, folks. They won't report it."

Legal experts, like University of California — Berkeley professor Orin Kerr, were bewildered over why Habba sought praise for her behavior. "As far as I can tell, she's claiming that the lawsuit was totally meritorious, and therefore the sanction for bringing a frivolous suit is itself a newsworthy event that reveals the corruption inherent in the system," Kerr said on social media. "This is very strange, added national security attorney Mark S. Zaid on X (formerly Twitter). "Apparently she wants publicity about how unethical a lawyer she is."

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.

In a civil fraud trial levied against Donald Trump by New York Attorney General Letitia James in 2023, Alina Habba frequently locked horns with Judge Arthur Engoron in nearly every courtroom proceeding. A lot was riding on this trial for Trump, who stood to surrender at least $250 million in sanctions if he lost. At one point she stood firm with colleague Christopher Kise, who objected to Judge Arthur Engoron's frequent whispering and note-passing with his law clerk, Allison Greenfield. "I have the same, frankly, issues with the person sitting on the bench, and I've made that clear on the record," said Habba, per ABC News.

When Engoron hinted that some misogyny might be at play among the Trump team's objections to the clerk's actions, Habba declared that the fact that she was a woman would kibosh such an assertion. Engoron responded angrily, per HuffPost, "I have an absolute, unfettered right to get advice from my principal law clerk." But the magistrate wasn't done. Having already placed a gag order on Trump for social media comments threatening his staff, Engoron extended it to include Habba and the rest of the legal team. "The First Amendment right of defendants and their attorneys to comment on my staff is far and away outweighed by the need to protect them from threats and physical harm," indicated the judge, per CNBC. Trump had already been fined $15,000 for violating the order.

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."

After Donald Trump was found liable for the sexual abuse and defamation of writer E. Jean Carroll in 2023, court reconvened in January. This time, Carroll was suing Trump for other instances where he defamed her, and the former president's lawyer, Alina Habba, planned to argue that the writer personally benefited from his verbal attacks. It didn't go well, especially during the second day. Judge Lewis Kaplan reprimanded her 14 times that day, lecturing her on basic legal procedures. Amusingly, at one point while Habba was cross-examining Carroll, the writer's counsel objected, prompting Kaplan to ask why. "I don't know what she's talking about," replied Carroll's lawyer, per Business Insider. "Neither do I," noted Kaplan.

But things got a bit stranger when Kaplan turned down Habba's request to postpone proceedings so that Trump could attend his mother-in-law's funeral in Europe. After Kaplan reminded Habba that Trump could be represented by legal counsel in his absence, Habba admitted, per Newsweek, "I don't know how to try this case, Your Honor." Legal experts quickly jumped on that admission and other gaffes, including Habba's failure to stand when addressing the court. "These are pretty basic things most lawyers kinda know," said former prosecutor Ron Filipkowski on X (formerly Twitter). "From my perspective, I would regret having her represent him," said Tim Parlatore, a former Trump attorney, on CNN. "I do think that in both of these trials, he was essentially undefended. And I think that it could have turned out differently."

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.

Donald Trump and his lawyer, Alina Habba, were understandably crushed on January 26 when the jury awarded $83.3 million to E. Jean Carroll, who successfully sued the former president for defamation. Adding insult to injury was that Carroll initially sought $10 million in damages before the trial started. But Habba wasn't done. The following week, she notified the case's presiding judge, Lewis Kaplan, about a New York Post story claiming that he had previously mentored Carroll's lawyer, Roberta Kaplan (no relation), when they were at the same law firm in the 1990s, hinting that such a relationship had a bearing on the trial's outcome. In response, Roberta Kaplan said the two had never connected since it was a large firm and both were at different levels of legal practice. "While Ms. Habba ends her letter by characterizing this as a 'troubling matter,' wrote Kaplan, per The Hill, "what is actually troubling is both the substance and timing of her false accusations of impropriety by on the part of E. Jean Carroll's counsel or the Court."  After Kaplan threatened sanctions, Habba withdrew the matter.

Not surprisingly, Trump plans to appeal the ruling. On Truth Social, he posted that he was interviewing lawyers, suggesting it was unlikely Habba would be part of the team. "Any lawyer who takes a TRUMP CASE is either "CRAZY," or a TRUE AMERICAN PATRIOT," he wrote, per Newsweek. "I will make my decision soon!"