Table of Contents
- Former President Donald Trump hired a low-profile lawyer to represent some of his most personal cases.
- Alina Habba is defending him in sexual assault cases and suing the NY AG leading the Trump Org. probe.
- Experts say Habba hitching herself to Trump carries great reputational risks.
On Thursday, Donald Trump had an important court hearing. New York Attorney General Letitia James subpoenaed the former president for her civil investigation of the Trump Organization’s finances. Trump didn’t want to sit for a deposition and asked his lawyers to fight it.
New York State Supreme Court Judge Arthur Engoron brought all the parties together in a
conference to hear everyone’s positions. In his corner, Trump had someone who was far from the national radar: a 36-year-old lawyer named Alina Habba.
At times, Habba treated the court hearing like a Fox News appearance, inquiring why the New York state Attorney General’s office would not investigate Hillary Clinton instead of Trump. Engoron’s law clerk told her several times to stop interrupting him.
In the end, Engoron ordered Trump, Donald Trump Jr, and Ivanka Trump to sit for depositions within 21 days. Habba’s arguments didn’t work.
Since first hiring Habba in September, Trump has sicced her on his most personal court cases, ones like the initial showdown she just lost. In addition to defending her against two sexual assault lawsuits, she also filed a lawsuit against the New York Times and the ex-president’s niece, Mary Trump, over leaking his tax documents.
She’s also handling Trump’s most audacious lawsuit yet: an attempt to stop Tish’s investigation outright.
That case is a long shot, experts told Insider. It also comes with the devil’s bargain job of being Trump’s latest go-to lawyer, a position that has led some of her predecessors into situations that could be almost impossible to navigate ethically. Consider, for example, when Trump tried without success to get his Don McGahn to fire Robert Mueller and the White House counsel then ended up becoming a star witness in the special counsel’s final report.
“The easiest way to get a high profile is to represent Donald Trump,” said Randy Zelin, a New York-based criminal attorney and Cornell Law School professor. “Now, is it worth it?”
Take it from someone who knows. For years, Michael Cohen served as an executive for the Trump Organization and personal attorney for Trump, acting as his go-to fixer for legal problems. In 2016, his work on behalf of Trump — paying a hush-money payment to Stormy Daniels — led to a criminal conviction and disbarment.
“For Donald, the only option is victory at any cost,” Cohen told Insider. “This even includes having counsel act in ways detrimental to their reputation and career.”
“If she falls down the garbage chute I did,” he said. “I predict a very bad ending.”
Habba did not respond to requests for comment for this story.
Habba represented another businessman suing media companies before Trump hired her
Habba attended Widener University Commonwealth Law School in Delaware between 2007 and 2011 according to her LinkedIn profile. McGahn, the former Trump White House counsel, graduated from the same law school in the 1990s, as did former associate White House counsel Jim Schultz. Then-Sen. Joe Biden also taught at the institution’s sister law school, Widener University Delaware Law School, from 1991 until 2008, overlapping with Habba’s attendance.
After graduating from law school, according to her LinkedIn profile, Habba spent several years at small law firms before founding her own, Habba Madaio & Associates LLP, in 2020. With her partner Michael Madaio, the firm focuses mostly on helping businesses with miscellaneous legal issues. She had also, at one point, been the general counsel of a parking garage company, according to the Washington Post.
Before representing Trump, Habba’s biggest brush with fame was in July, representing “Real Housewives of New Jersey” star Siggy Flicker. Flicker claimed she was banned from Facebook after wishing Melania Trump a happy birthday. Habba wrote a letter to Facebook on her behalf, which the social media company appeared to ignore. Habba never actually filed a lawsuit over the scuffle, and it faded away.
Court records show that Habba has been involved in a handful of dramatic cases. Among the highlights is a class action lawsuit representing several students at the University of Bridgeport, in Connecticut. The students, according to the lawsuit, were charged thousands of dollars in fees for on-campus services even as classes were held online because of the coronavirus pandemic. In another case, she’s representing a New Jersey man who sued a nursing home, alleging it didn’t properly care for his uncle as COVID-19 cases surged. Both cases remain pending.
In July, Habba filed a lawsuit in federal court in New Jersey on behalf of Caesar DePaco, a Portuguese businessman who runs a vitamin supplement company with a “thin blue line” flag on its website, against Cofina, a Portuguese media organization.
The lawsuit says a magazine that Cofina owned defamed DePaco when it published a story alleging he is the “main financier” of Chega, a far-right political party in the country, and “engages in criminal activity and illegal forms of intimidation to collect debts” — all of which DePaco denies. Cofina moved to dismiss the lawsuit, telling the judge that DePaco didn’t have the jurisdiction to sue the company because it is based in Portugal and not New Jersey.
Despite Trump’s frequent complaints about “fake news,” he has sued media companies only three times during his presidency. In all of those cases, he was represented by Charles Harder, the defamation attorney famous for taking down Gawker in 2016.
In September, Habba filed her first lawsuit on behalf of Trump. In New York state court, she sued the New York Times and Mary Trump, his niece, who had leaked boxes of his tax documents to the publication. The lawsuit alleged Mary Trump violated a confidentiality agreement she signed in 2001 when she handed over those tax documents and claimed Times journalists “aided and abetted” that violation.
“The defendants engaged in an insidious plot to obtain confidential and highly-sensitive records which they exploited for their own benefit and utilized as a means of falsely legitimizing their publicized works,” Habba wrote in the lawsuit.
Mary Trump, filed a motion to dismiss the lawsuit in December, claiming the 2001 settlement was designed to swindle her out of money that was rightfully hers (she filed a separate lawsuit against Donald Trump in 2020).
Habba helped wrap up one of Trump’s longest-standing legal problems
It’s not clear how Habba and Trump first met.
She has never donated to him or any other politicians, according to a search of Federal Elections Commission records.
Her firm, however, is based just an eight-minute drive from the Trump National Golf Club in Bedminster, New Jersey. Trump lived at the private club in the summer of 2021 and often golfed there during his presidency. According to Axios, Habba “got to know” Trump by visiting the club.
Habba publicly staked her claim in Trump’s legal world on September 3. Court records show that, on that day, she swapped in for attorney Marc Kasowitz in a case filed by Summer Zervos. Kasowitz has been one of Trump’s longest-serving lawyers, handling personal issues for him since before his presidency and working on politically charged cases for him in 2017.
Zervos, in 2017, filed a defamation lawsuit against the then-president in New York state court, claiming he sexually assaulted her twice and then defamed her when he called her a liar.
Habba, in a hearing a month after she joined the case, was aggressive. She reiterated Trump’s arguments that the case had no merit, and threatened to file an anti-SLAPP motion, which would allow him to potentially recoup legal costs if he won the case.
Michael Rand, a law clerk overseeing the hearing, was unimpressed. He said that both Trump and Zervos needed to sit for depositions by Christmas.
Just weeks later, on November 12, Zervos dropped the case. The court filing says that each party would “bear his or her own costs.” Zervos’s attorneys said she “accepted no compensation” and “stands by the allegations in her complaint.”
While Zervos was still free to continue publicly calling the former president a rapist, Habba still succeeded in cleaning up a legal headache. Her success may have given Trump a reason to assign her to another case: E. Jean Carroll.
In 2019, the columnist publicly accused him of sexually assaulting her in the mid-1990s. Like Zervos, she sued him in September of 2020, after he called her a liar and insulted her appearance.
Habba joined on November 22, also replacing Kasowitz. She once again went on the offense. In a lengthy counterclaim filed on January 11, she said Carroll lied about Trump in order to boost sales for her book released in 2019.
She also threatened to sue the Pulitzer Board for prizes it didn’t award
In November, Habba threatened to file a lawsuit against the Pulitzer Prize Board. She demanded it retract the 2018 Pulitzer Prize for National Reporting given to the Washington Post and New York Times for their stories about Russia’s interference in the 2016 election and how Trump fired FBI director James Comey.
The letter to the board came after Special Counsel John Durham accused Igor Danchenko, a Russian national, of lying when he provided information for what later became known as the Steele Dossier. The document played a role in a wiretap application for a foreign policy advisor for Trump’s 2016 campaign who had ties to Russia as part of a larger FBI investigation into Russia’s election interference.
The New York Times didn’t correct any of its stories in the wake of the admission, and there’s no evidence any of its stories relied solely on Danchenko’s claims. Habba’s letter does not identify any such stories.
The Washington Post corrected two stories following Durham’s indictment. Neither of them are among the articles that were awarded a Pulitzer Prize. Habba’s letter also refers to complaints about CNN’s coverage of the Steele Dossier, which was not even a finalist for the prize.
Bud Kliment, the administrator of the prizes, told Insider that the Pulitzer Board has a “standing process for reviewing questions about past awards.” He did not respond to additional questions about whether Habba or another representative for Trump had triggered the process.
Habba has not yet filed a lawsuit against the Pulitzer Board. Zelin told Insider that having “one client,” as Habba does with Trump, can put an attorney in situations that risk their credibility.
“Your reputation, and as the old saying goes — it takes a lifetime to build a reputation in about 10 seconds to destroy it,” Zelin said.
Her biggest gamble yet is a challenge to New York Attorney General Letitia James
To stop New York Attorney General Letitia James’s subpoena of Trump, Habba filed a lawsuit in federal court on December 20 asking for an injunction that would freeze the investigation entirely. She argued the investigation was an abuse of power, since James, as a candidate for attorney general and governor, had bragged about suing Trump.
Habba also took her argument to right-wing media. In an interview with Sean Hannity on Fox News in January, she said James was running a “fishing expedition” and that real estate valuations are “incredibly subjective.”
With Engoron’s ruling on Thursday that Trump had to comply with the subpoena by mid-March, it’s unlikely the federal judge in Habba’s case will issue a ruling in time. And Zelin said it had little merit in the first place.
“What Trump wants us to do is he wants us to talk about everything else but the 800-pound gorilla in the room,” Zelin said. “Which is, did you lie about the value of properties? Did you deceive lenders? Did you deceive insurance companies? Did you deceive the IRS?”
If Habba chose to work for Trump in order to advance her reputation, Zelin said, then she is playing a dangerous game.
She may be able to command higher fees in the future, he said. But while big legal names like Kasowitz, Harder, and Rudy Giuliani have established track records, Habba runs the risk of making it impossible to disconnect from the former president.
“You become radioactive. You become typecast,” he said. “You just can never play any other role.”
One lawyer who faced off against Habba in a now-completed case, and who spoke on the condition of anonymity because they were not authorized to discuss it, said they found Habba to be “perfectly competent.” But having a client like Trump presents risks, the lawyer said.
“In the legal profession, your reputation is everything, your credibility is everything,” the lawyer said. “But once you go down the path of being so connected with one person, who may not want you to uphold those standards, you can end up in really difficult spots.”
The worst-case scenario may be if, one day, Habba has to stand up to Trump.
Whether it’s Michael Cohen, former Attorney General Jeff Sessions, Senate Minority Leader Mitch McConnell, or former Vice President Michael Pence, Trump has sought to ruin the reputations of people who refused to do his bidding.
“Hitching your wagon to Donald J. Trump is not a wise move for a young and aspiring attorney,” Cohen said. “Unfortunately for Ms. Habba, the matters to which she is representing Donald on have highly skilled counsel that she will need to wrangle with.”
“I don’t see her achieving success in these matters,” he added.