Alina Habba's Most Awkward Media Moments To Date

When Alina Habba was noticeably absent from the courtroom at the start of Donald Trump's "hush money" trial in Manhattan on April 22, 2024, rumors swirled that there had been a falling out between the two. But never fear; Trump and his glamorous attorney, Habba, are still very much a team, just not for any of his four criminal cases. That's not Habba's field of expertise. "Obviously, you know, being a type A person, I wish I was a criminal attorney, but I'm not," Habba told "The Benny Show" on April 16. "But the great news is that then I can do this and let everybody know what is actually happening."

Habba's commitment to "doing this" means releasing what she considers bombshell information from inside the courtroom. Habba's vow to spin the trial proceedings is a mixed blessing for Trump's criminal team, given her record of media moments that are beyond awkward.

Habba and Trump have a lot in common. She angers quickly and isn't afraid to vent at what she perceives as miscarriages of justice. Habba likes to flaunt her hefty Trump paychecks and live a wildly lavish lifestyle even for a high-flying attorney. She also has yet to meet a camera she doesn't like, seemingly adoring any media coverage, and she's a social media whiz with over 304,000 Instagram followers as of May 2024. So, why are so many of Habba's media moments so unbearably awkward? Let's take a look back.

Donald Trump has raised eyebrows for blowing over $40 million of campaign funds from a super PAC to cover his legal fees. It's a questionable use of the donations that Alina Habba dutifully defended. She went on Charlie Kirk's Real America's Voice show in August 2023 to present an explanation for Trump pilfering his campaign coffers, which resulted in one of Habba's more awkward media moments.

As of April 2024, Trump was staring at an estimated $86 million in legal fees. It's an overwhelming amount, even for a self-professed billionaire. However, the Save America PAC is apparently 100% behind Trump and his cronies using the funds for their various legal charges including the classified documents case out of Florida. PAC spokesperson Steven Cheung told The Washington Post that covering the legal fees will "protect these innocent people from financial ruin and prevent their lives from being completely destroyed."

Habba's justification to Kirk was even more outlandish. She insisted (via MeidasTouch) that the use of the funds was legal and that "when you support the president, you support getting him into office," rather than jail, presumably. Habba also argued that Trump is being unfairly targeted by his detractors, and that there's nothing wrong about using donors' funds to bankroll his personal expenses. Habba urged the public to examine the cost of the DOJ's meritless attack against Trump instead. However, she didn't encourage anybody to scrutinize how much of that $40 million has been paid to her. Nothing to see here! Move along now!

Alina Habba is a pro at awkward media moments. Still, her fury-fueled attack against Letitia James, the attorney general in Donald Trump's NYC civil fraud trial, was unhinged even by her standards. In a statement outside the courthouse on November 6, 2023, Habba claimed it was clear that James had a vendetta against Trump. "[She] had predetermined my client had committed fraud even before we walked into this courtroom," Habba charged (via Forbes), perhaps not realizing that an attorney general presumes they have enough evidence to prove a defendant's guilt before charging them with an alleged crime. Habba also complained, without a hint of irony, that James just wanted "to make a name for herself."

The heated press conference was a fitting end to an explosive trial. Later that same day, Habba told Newsmax that Judge Arthur Engoron was out of line for slamming the table in frustration during Trump's rambling testimony and ordering Habba to sit down. Habba took things even further by accusing Engoron of silencing Trump because "he was giving tremendously accurate and good testimony." Later in the interview, Habba resumed her attack on Letitia James by labeling the attorney general as a radical left-wing partisan. Habba also insulted James by saying she's "just not that bright."

In February 2024, Alina Habba was back on her MAGA mouthpiece of choice, Newsmax, which resulted in another cringe-worthy media moment. This time, Habba ranted about Judge Lewis Kaplan, the federal adjudicator overseeing Donald Trump's defamation trial. Spoiler alert: Trump lost and was ordered to pay $83.3 million to E Jean Carroll for calling her a liar over her claim that he sexually assaulted her in 1996.

"Our Legal System is out of control and being used as a Political Weapon. They have taken away all First Amendment Rights. THIS IS NOT AMERICA!" Trump ranted on Truth Social (via Twitter), blaming everything on a "Biden-directed witch hunt" against him and the GOP.

In an interview with Newsmax's Eric Bolling (via The David Pakman Show) Habba continued Trump's assault on the legal system. She railed against Judge Kaplan for threatening to throw her in jail. "You know, we have a judge who's trying to throw a civil attorney, threatening me, that he's going to put me in the clink," Habba said. "Because I objected to his ruling on an evidentiary issue." According to Habba, she merely failed to enter a PowerPoint slide into evidence, but there was more to the story. Per Newsweek, ahead of the evidentiary issue, Kaplan and Habba had already engaged in a heated altercation over a Newsmax clip where Trump disparaged Carroll. On top of that, Kaplan was also furious that Habba and her client had arrived late to court for the closing arguments.

Alina Habba continued her awkward media streak during a March 2024 appearance on "Jesse Watters Primetime." Habba was on the show to discuss the Supreme Court's unanimous ruling regarding Donald Trump remaining on the Colorado ballot. However, the interview kicked off on a bizarre note and didn't improve from then.

Watters asked Habba if she planned to send former MSNBC anchor Keith Olbermann a pair of Trump's gold sneakers. "Yes, I am, and I'm going to put them in a case so he can look at them forever," Habba replied. "Look at eBay and see how they're selling for $450,000." (Per Newsweek, that purchase has yet to be verified.) Watters claimed he couldn't understand why anybody was shocked the sneakers would sell for so much. "Everybody knew it was going to happen," he insisted. Habba then steered the discussion away from sneaker talk and moved on to the memes of women shedding "liberal tears" after Trump won the 2016 election. Habba argued there was a similar reaction to the SCOTUS ruling that kept Trump on the Colorado ballot.

"Imagine crying because the Constitution is standing strong, and we're not going to turn into Cuba," Habba said. "That's Trump Derangement Syndrome 101, right there. Because the Constitution was upheld today," she continued, claiming the SCOTUS ruling proved the U.S. wasn't a "third world country" or a banana republic. "MSNBC, CNN, and 'The View' all threw tantrums [over the ruling]," Habba claimed before launching into a campaign speech. "It's about America first, it's not about Trump, It's about us."

There have been whispers in Washington D.C., and the halls of Mar-a-Lago, that if Donald Trump secures a win in November 2024, Alina Habba will have a prominent role in his administration. It's a rumor that seemed increasingly likely, given Habba's announcement (via The Independent) that she will be "spitting the truth" for Trump as an official spokesperson and telling "people facts they may not be hearing in court." Whether they'll be fact-facts or alternative-facts remains to be seen.

As a demonstration of the "facts" that Habba will bring to the table, she accused the judge in Trump's hush money trial of having a personal vendetta against the former president. "Once again, Sean, we have a judge who has clear ambitions and political motivations," Habba told Sean Hannity on May 6, 2024. She claimed Judge Juan Merchan told the court that he was willing to throw Trump into jail and referred to him as "possibly the next president." Habba said she was stunned by that remark even though Merchan was correctly stating a potential outcome of the 2024 election. Instead, she painted the remark as an admission that Merchan thinks Trump will win and is conspiring against him.

Habba also went on to claim that Judge Merchan threatened to incarcerate Trump for speech that Habba claimed was not her client's fault. According to Habba, Trump had merely shared provocative social media posts about the trial created by his MAGA supporters. For the record, that sharing was a direct violation of the gag order, and it was not the first time Trump had defied the order either. It was the 10th time, according to CNN. Despite the numerous infractions, the former president was only penalized with fines in an effort to dissuade him from future violations that could result in jail time.

Alina Habba finally scored a win for Donald Trump when the estimated $464 million bail bond for his civil fraud case was reduced to $175 million. Don Hankey, a billionaire buddy of Trump's, shared the good news with NBC News, saying he was willing to pay a much higher amount than the state finally agreed upon. "We are extremely pleased with the ruling issued by the Appellate Division," Habba said in a written statement. "This monumental holding reigns [sic] in Judge Engoron's verdict, which is an affront to all Americans."

Habba must also have been pleased by the good news. She had been on a losing streak since starting work with Trump in September 2021. Habba's multiple awkward media moments, outspokenness, willingness to engage in heated debates, and unwavering support of Trump have made her a controversial figure and a target for mockery.

In fairness, Habba doesn't do herself any favors. During a January 2024 interview on the PBD podcast, Habba confessed that she always puts looks over brains any day of the week. "I don't think I'd be on TV or sitting here if I didn't look the way I look," she shared. "It doesn't hurt to be good-looking." Habba also admitted she can "fake" being smart but usually doesn't need to. "People think that President Trump hired me because I'm good-looking. That is absolutely not the case," she insisted.