Embarrassing Alina Habba Moments That Prove Why She's Trump's 'Worst Lawyer'

It's no secret that Donald Trump has a long history of surrounding himself with some of the worst lawyers money can buy. From Rudy Giuliani, who got disbarred in July 2024, to Lindsey Halligan, who was tapped to be the United States Attorney for the Eastern District of Virginia until a judge deemed her appointment was legally invalid, Trump has worked with a cadre of embarrassing attorneys. However, it's Alina Habba who has repeatedly distinguished herself as Trump's very worst attorney time and again, in some spectacularly strange ways.

Habba has proven just how ineffective she is as a legal professional, both when it comes to her skills as a lawyer and when it comes to her talent for putting her foot in her mouth in front of an audience. Whether it's her mistake-laden lawsuit filings or her amateurish legal battle against Hillary Clinton that ended up costing her and Trump nearly $1 million, Habba doesn't seem to have a good grip on the nuances of the actual legal process. She hasn't shown a ton of good judgment when it comes to public appearances either — just look at her decision to dance in a bedazzled jean jacket at Trump's Madison Square Garden rally.

Even Trump's former lawyers seem to dislike Habba. In January 2024, when Habba failed to successfully defend Trump in a defamation lawsuit filed by E. Jean Carroll, Trump's ex-attorney Ty Cobb slammed Habba on CNN for trying to win the case using mafia-like intimidation tactics, regardless of their legality. Even then, Habba still couldn't keep Trump from having to pay Carroll $83 million – and that's still not one of the most embarrassing examples of exactly how Habba is Trump's worst lawyer, hands down.

Getting publicly removed from office by a panel of federal judges definitely feels like an embarrassing career milestone. However, Alina Habba doesn't need a legal showdown or a panel of experts to humiliate her in public — she can do that all by herself. This is exactly what happened in March 2026 while she was speaking with anchor Ed Henry during a Newsmax appearance. Habba — who began serving as a senior advisor to Attorney General Pam Bondi in December 2025 — was railing against Kamala Harris speaking out against Trump at the funeral of civil rights icon Jesse Jackson. The only problem is, Habba got a key detail wrong in her rant. See if you can spot the error: "I think if you look at polls, Kamala Harris' comments of desperation at Reggie Jackson's funeral, and she didn't even know him. You know, if you look at this, they're reaching so far," Habba exclaimed.

Alina Habba condemns Kamala Harris's remarks at Reggie Jackson's funeral. (It was Jesse Jackson). pic.twitter.com/5kCpn5qtkB

— Ron Filipkowski (@RonFilipkowski) March 10, 2026

If you didn't catch the mistake, Reggie Jackson is a retired baseball Hall-of-Famer who was 79 years old and very much alive at the time of Habba's interview, and not the legendary civil rights leader Jesse Jackson, an outspoken critic of Trump, who died in February 2026 at the age of 84. Although considering how many of Habba's different court filings were absolutely riddled with errors, perhaps it should be no surprise that she didn't get Jackson's name exactly right.

For months, Alina Habba served as the interim United States Attorney for New Jersey, an important legal role that made her responsible for enforcing and overseeing the litigation of federal cases. The position was a temporary one that technically expired, which would have required Habba to get confirmed by the Senate if she wanted to maintain the role. Trump, however, allegedly decided to take questionable steps that would allow her to stay in the position without going through the confirmation process, and the courts quickly caught on to the scheme.

In December 2025, the 3rd U.S. Circuit Court of Appeals came to the decision to uphold a previous lower court ruling that disqualified Habba from being the U.S. Attorney for New Jersey. Despite her protestations, the panel of three wrote (via AP News) that Habba should in fact be barred from the job, and that her being in that position was an example of how the Trump administration "has been frustrated by some of the legal and political barriers to getting its appointees in place," so they decided to just skirt the law.

Habba's disqualification has also had some wider-ranging effects. After she was forced to leave the position, Attorney General Pam Bondi replaced her with three lawyers who were meant to split the workload between them. In March 2026, CBS News reported that the same federal judge who initially disqualified Habba ruled that hiring three people for the same role was against the Constitutional Appointments Clause, leading to even more drama and conflict.

People will often try to recontextualize their losses as victories. Alina Habba, however, made headlines when she decided to just brag about an embarrassing loss as if it were a good thing to a crowd of supporters. The often-ridiculed lawyer took the stage at the Turning Point USA conference in Phoenix, Arizona, in December 2023, and boasted about her efforts to file lawsuits on behalf of Donald Trump against Hillary Clinton, former FBI director James Comey, and the Democratic National Committee, among others. The thing is, Habba's lawsuits were all thrown out, and the judge in the case even sanctioned her and Trump to the tune of nearly $938,000.

In Habba's mind, however, this proved just how good a lawyer she is! She clearly tried to express this while addressing the crowd, bragging about how tenacious she was in her legal battle against Clinton. "It got assigned to a Clinton-appointed judge. And what do you think happened? Nobody's heard of the case, right? Because it's gone. I never met the judge. I never walked into the courtroom," Habba said, as seen in a clip posted to X, inexplicably gloating at what she suggested was some sort of political conspiracy. "One month, it got dismissed, and me and President Trump got sanctioned a million dollars for going against crooked Hillary. ... But guess what? We paid that million, and we're going to keep on fighting."

Trump's lawsuit was dismissed in September 2022, and the presiding judge sanctioned Trump and Habba the following January. The judge wrote (per Newsweek) that Trump and Habba's "legal theories were frivolous" and the sanction was imposed because of Trump's history (and perhaps passion for) "misusing the courts to serve political purposes."

There's always something cringey about politicians dancing to music — just look at the many, many examples of Donald Trump's painfully awkward dancing moments. It turns out this also applies to lawyers who try to look cool, like when Alina Habba came out to address the crowd at Trump's political rally at Madison Square Garden in New York City in October 2024. Rocking one of her many, many super tacky outfits — a sequined jacket with "MAGA" emblazoned across it — Habba decided to show off her hip and stylish moves as she walked along the platform to the podium on the main stage.

Hilariously, Habba's intro song was wonderfully ironic, just adding to the general vibe of surreal, tone-deaf awkwardness. Habba — who, you'll remember, failed to successfully defend Trump against E. Jean Carroll's $83 million defamation lawsuit — came out to DJ Khaled's "All I Do Is Win," without a single ounce of self-awareness. She grooved across the walkway as her sequined jacket shimmered in the bright lights of the famous venue before she got to the podium.

normal lawyer things pic.twitter.com/tS7Jq61loz

— Aaron Rupar (@atrupar) October 27, 2024

The awkwardness didn't stop there, of course. Habba then proudly laid out the jacket on the lectern in front of her, showcasing the deeply unflattering and gaudy accessory, before explaining why exactly she did so. "I put my MAGA jacket to trigger Hillary Clinton," Habba said, as if Clinton was actually watching. It's impressive Habba could afford such a glittery jacket, what with the hundreds of thousands of dollars she had to fork out for Clinton's legal fees the year before.