Everything We Know About Donald Trump's Attorney, Alina Habba

The following article includes references to racial slurs.

When former president Donald Trump decided to sue three reporters The New York Times and his niece Mary L. Trump over a 2018 story on his tax returns, he didn't turn to a big-name media lawyer. Instead, he chose the Bedminster, New Jersey-based attorney Alina Habba, founder and managing partner of Habba Madiao & Associates. Habba appears to be a virtual unknown in media law; instead, her law firm lists business and commercial litigation, insurance defense, real state, entertainment structure, and civil litigation as its main practice areas. 

According to The Washington Post, Habba's experience includes working as general counsel for a parking garage firm and representing Siggy Flicker, a cast member of the "Real Housewives of New Jersey." The suit was filed against Facebook, which is said to have disabled Flicker's account after she posted a photo of Melania Trump to greet the former first lady on her birthday (via Habba Madaio).

Here's what else we know about this enigmatic esquire who has continued to represent Trump in civil cases.

As Donald Trump's lawyer, Alina Habba's job is to represent him in court. However, the New Jersey native has also been known to support Trump's political aspirations — especially in the public sphere. This is evident on Habba's Instagram, where she has been known to pillar the "Make American Great Again" (MAGA) campaign. In October 2023, she shared a photograph of herself posing with a Republican rapper. The caption of her photo read "[Lil Pump] is all in on Trump. #MAGA LFG." She later followed this post up with a picture of herself with Trump, captioned: "Our country is in shambles. Are you awake yet?"

Habba's support of the MAGA campaign is not all talk — the lawyer has quite literally put her money where her mouth is. As reported by the Mirror, disclosure documents show that Habba's law firm, Habba Law, has donated over $1 million to Trump's political action committee, or PACs.

In addition to these financial commitments, Habba has made her politics known by becoming a senior advisor for the MAGA, Inc. PAC that raises money for Trump's campaigns. In this capacity, she has served as a spokesperson for the fundraising organization, even appearing on Newsmax to discuss advertising strategy. Another MAGA, Inc. representative told Bloomberg, "Alina Habba is an extremely talented individual who has become an important adviser to President Trump" (via Washington Examiner). According to the rep, Trump consults her on "legal matters [and] political issues."

Over the years, Donald Trump has stirred up quite a bit of controversy — something that his lawyer, Alina Habba, is also familiar with. In 2022, Habba's former legal assistant, Nasyia Drayton, filed a lawsuit, accusing the Jersey-based attorney of using racist and sexist language in the workplace. The civil suit alleged that Habba would sing inappropriate music in the office, particularly "explicit, highly sexualized" songs and raps containing the n-word. Drayton claimed that the alleged use of this language made her feel "humiliated, embarrassed, and uncomfortable" throughout the workday.

In addition to these claims, Drayton said that Habba made racially disparaging comments toward the Attorney General of the state of New York, Letitia James. According to Drayton's lawsuit, Habba once screamed "I hate that Black b***h!" after her legal argument was rejected in the New York Court of Appeals. The documents claim Drayton "was appalled about the racist remarks made about the Attorney General, Letitia James, and felt astonished that her supervisor, Defendant Alina Habba, felt comfortable and entitled to make such comments in the workplace, in her presence."

Although this suit did not go to court, The Daily Beast reported that Drayton and Habba were able to reach a settlement. Recordings of Habba's alleged comments apparently played a key role in negotiations. Drayton's lawyer, Jacqueline L. Tillmann, told the outlet that a "resolution" had been reached.

Nasyia Drayton's lawsuit was not the only time that Alina Habba has faced legal issues. As reported by NPR, Habba was fined in 2023 after filing a lawsuit in what U.S. District Judge Donald M. Middlebrooks described as "bad faith." The lawsuit — which Habba filed on behalf of her client, Donald Trump — named several of the former president's political foes as defendants. Hillary Clinton and former FBI Director James Comey were among two named in the lawsuit.

After examining the suit, Middlebrooks determined that it had no grounds. In a strongly worded filing, the judge condemned both Trump and Habba for ever having brought the suit forward, writing, "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 ruled that the issues with the lawsuit included "glaring structural deficiencies" and "characterizations of events [that] are implausible."

As such, Middlebrooks stated that Trump and Habba had only filed the lawsuit in revenge and were thus abusing the justice system. Thus, he ruled that Trump and Habba would have to pay approximately $938,000 to the people named as defendants in the case.

Alina Habba has generated controversy due to some choice words uttered outside of the courtroom. This became especially evident during Donald Trump's 2023 civil fraud trial. The case, which was brought forward by New York Attorney General Letitia James, alleges that Trump intentionally inflated the value of his assets by $2.2 billion.

During a lunch break after a long morning in court, Habba gave a press conference in which she launched a series of highly personalized attacks not only against James but also against the presiding judge, Arthur Engoron. As transcribed by CNN, Habba said of James, "She said this morning that the numbers [in Trump's financial statements] don't lie, and they won't lie in this case. Well, Ms. James, I have a message for you — the numbers didn't lie when you ran for governor, and that's why you dropped out." James ran for governor of New York in 2021.

In the same press conference, Habba also shared some controversial criticisms of Engoron, at one point calling him "unhinged," Newsweek reported. As she told a crowd of journalists, "Let me be very clear: I don't tolerate that in my life. I'm not going to tolerate it here. And, you know what, you shouldn't either." She went on to insinuate that the judge's decision was "undemocratic."

Although some members of Donald Trump's base supported the way that Alina Habba spoke about Judge Arthur Engoron, legal experts provided a different take. The reason for this is that, at one point in her lunch break press conference, Habba specifically complained about the way that Engoron had told her to sit down during the trail. "I was told to sit down today. I was yelled at. And, I have had a judge, who is unhinged, slamming a table," she told reporters. At another point in her speech, Habba described "courtrooms where attorneys are gagged. Where attorneys are not allowed to say what they need to say to protect their client's interests." These comments seemed directed specifically at Engoron.

According to some legal experts, however, it is fairly normal for judges to tell attorneys to sit in certain circumstances. As attorney and occasional television personality, Bradley P. Moss, wrote on X, formerly known as Twitter, "I have had the current Attorney General and a current Supreme Court justice, at the time serving in their respective positions on the DC Circuit, chastise me in two different proceedings." He then added, "Get over it." Katie Phang, who works as a legal analyst for MSNBC, expressed a similar sentiment in another X post, tweeting, "Spoken like a lawyer who: (1) doesn't try cases and (2) doesn't know how to act in front of a judge."

Although Alina Habba is best known as Donald Trump's attorney, she also has a busy personal life. The lawyer has two children, Chloe and Luke, who take a prominent spot on her social media. She also has a dog, Fritz, which Habba said she bought for her daughter out of "mom guilt." Photos of Habba and her kids show them engaging in various activities, ranging from golfing to boating to traveling through airports on various vacations. 

In addition to spending time with her children, Habba enjoys the company of her husband Gregg Reuben, a Harvard Business School graduate and CEO and founder of Centerpark. The couple married in 2020. Habba was previously married to a fellow attorney, Matthew T. Eyet. Like Habba, Eyet also founded a law firm. Eyet Law, based in New Brunswick, New Jersey, opened in 2019, although Eyet practices in Pennsylvania and New York in addition to New Jersey.

On top of being Donald Trump's legal advisor and political supporter, Alina Habba appears to have a personal friendship with the former president. As revealed by her Instagram, Habba spends a good deal of time with Trump, oftentimes in the company of her children. In one video Habba shared on Instagram, she is seen standing beside her daughter Chloe as the young girl sticks her hand out for Trump to sign. "Aw," Habba gushed before shouting, "You can never shower again!" A photo shared in the same post reveals Trump's message to the child, "I love you! D."

This was not the only time that Trump has spent time with one of Habba's kids. In a separate Instagram post, the lawyer shared photographs of her son Luke sitting next to the politician on his private plane. The post's caption reads, "Grateful for these epic memories with the G.O.A.T. ... on Trump Force One." Habba's kids have also been featured together in an advertisement for "Letters to Trump," which, according to 45Books, is the former president's "second official book" since leaving office.

Beyond this connection, Habba and Trump have been spotted at many of the same social events. On the lawyer's 39th birthday, she was photographed with the politician in front of her birthday cake. She has also been described as a frequent visitor at Trump's Mar-a-Lago and a member of his golf club in Bedminster, New Jersey. 

Over the years, many women in high-profile positions have complained that people pay attention primarily to their appearances — and it looks like that could be true for Alina Habba. Since the beginning of Trump's 2023 civil fraud trial, the lawyer has been compared to Melania Trump. Users of X, formerly known as Twitter. have gone so far as to roast Alina over her resemblance to the former first lady. As one user tweeted, "Can someone please tell [me] why the so-called Attorney Alina Habba makes sure she looks like Melania Trump every day?" Another retweeted a photo of the attorney with the caption, "Looks like the next Melania to me."

Fascinatingly, though, Habba is not the only member of Donald Trump's team who has been compared to Melania in the past. In fact, there was once an instance in which Fox News actually misidentified the former president's assistant, Margo Martin, as his wife. As reported by Newsweek, the trouble started when Fox News anchor John Roberts spotted the long-haired Martin as she waited patiently for Trump's arraignment in Miami. He mistakenly identified the aide as Melania, before later apologizing. "With a day like today, with so many comings and goings, it's easy, from a distance, to mistake two people," the journalist said.

Between working as a lawyer and parenting her children, Alina Habba seems to have her hands full. However, the high-profile attorney does appear to have time for at least one hobby — shooting. And, from what she has said in interviews, Habba feels that this is an important right.

For an appearance on "The Benny Show" in 2023, Habba showed up wearing a necklace with a pistol charm, which she paired with an American flag-themed t-shirt. When asked about her choice of jewelry, Habba responded, "Oh, I am a gun lover. Are you surprised? I do own guns. I do shoot" (via Raw Story). She went on to add, "God and guns. I've got God and guns. That's it."

Later on in the interview, Habba established her feeling that the rights outlined in the Second Amendment are important. "You know, people keep asking me the same questions. CNN and whatever I go on, they think they're going to get me in a corner with, you know, your client [Donald Trump] said 'protest.' Absolutely. That's another right. That's another right in this country. Just like guns. Just like God. It's a right. Don't mess with our rights."