Awkward Alina Habba Moments That Made Us Cringe

Donald Trump has always been a polarizing figure. When he was a real estate mogul, many hated his acquisition of iconic New York City buildings, while others reveled in the perceived grandeur of the Trump Tower. Transitioning into politics only heightened the divide, with Trump amassing both fervent supporters and staunch critics, proving there's no middle ground when it comes to the disgraced businessman. Notably, the polarizing approach extends to the people closest to the former president, including those who work for him, subjecting them to intense public scrutiny for simply being associated with the Trump surname.

Alina Habba stands out as one of the key figures of media interest when it comes to Trump's legal team. Based in New Jersey, Habba joined Trump's legal team in 2021, serving as both an attorney and a legal spokesperson as needed. However, it appears that working for Trump means adopting his controversial behavior when doing, well, anything, and it often results in less-than-desirable outcomes for Habba.

Since stepping into the spotlight, the attorney had a number of awkward moments that made us thoroughly cringe. From contentious remarks to stealing the spotlight at trials for all the wrong reasons, Habba is no stranger to sounding like an amateur. Here are her top five most awkward moments, but brace yourself — you might experience severe second-hand embarrassment.

With the media abuzz with Donald Trump's 2024 hush-money case, Alina Habba seems to be subconsciously keen on making it a bigger spectacle than it already is. Trump was accused of falsifying business records to conceal alleged payments meant to silence his rumored mistresses, Stormy Daniels and Karen McDougal, an adult film star and a former Playboy Playmate, respectively, ahead of the 2016 presidential election.

Despite Todd Blanche and Susan Necheles serving as Trump's lawyers in the hush-money case, Habba wiggled her way into the narrative. Having previously acted as Trump's attorney, Habba took on the role of a legal spokesperson for the controversial businessman as he attempts to prove his innocence yet again. However, her performance has been less than stellar, as she seemed to imply Trump was indeed guilty in the hush-money scandal. Addressing the press outside the Manhattan courthouse on April 22, 2024, Habba said, "We're here because of something that happened when he was in the White House that wasn't even wrong. It was not wrong" (via Newsmax). She added, "You hire lawyers to solve problems; lawyers solve those problems; you pay them. That's it!"

Furthermore, given the 34 felony charges Trump is facing as of May 2024, it seems overly subjective to say his actions were not wrong. Still, Habba made sure to deliver her designated dose of cringe to the public, marking one of her most awkward episodes to date.

Another one of Alina Habba's awkward public statements about Donald Trump stirred controversy, prompting widespread concerns about his ethical conduct. Speaking about the former president on national television, whom she once described as "the most ethical American" during an appearance on Fox News, Habba subtly confirmed Trump wouldn't oppose receiving financial assistance from a foreign country to cover his $464 million civil fraud judgment.

In a March 2024 episode of "The View," co-host Joy Behar suggested that Trump would be willing to accept funds from countries such as Russia and Saudi Arabia to settle his legal expenses. The topic was later addressed during another appearance on Fox News, where Martha MacCallum, host of "The Story," asked whether there were any attempts by Trump's team to obtain funds from other countries, as Behar had implied. Rather than outright denying the suggestion, Habba gave an elaborate answer to the posed question, which notably lacked a negative response.

"Well, there's rules and regulations that are public. I can't speak about strategy; that requires certain things, and we have to follow those rules," the lawyer said, continuing on about how Trump's civil fraud judgment was unfair. MacCallum, while refraining from commenting on Habba's response, did appear puzzled. Similarly, X users echoed the sentiments of the Fox News reporter, expressing their disbelief on the platform. "She just confirmed it," read one tweet, while another pointed out, "Trump is for sale."

During the second E. Jean Carroll defamation trial in early 2024, Alina Habba served as Donald Trump's lawyer and was painfully bad at it. Carroll, a writer, had sued Trump for damaging her reputation by dismissing her sexual assault accusation from the 1990s as false. On January 17, 2024, Habba was reprimanded for several legal mishaps during the court proceedings, giving the impression that she bit off more than she could chew. Notably, Senior U.S. District Judge Lewis Kaplan had to repeatedly instruct her to sit down, which she later described as abusive behavior when speaking to the press.

Notably, when Habba and Michael Madaio, another one of Trump's attorneys, attempted to introduce previously unlogged X posts as evidence, Kaplan wasn't having it. According to Politico reporter Erica Orden, Kaplan warned Habba, "You are on the verge of spending some time in the lockup. Now, sit down," as shared on X.

Shortly after, Habba requested an adjournment for the next day's hearing due to the death of Amalija Knavs, Trump's mother-in-law, but her request was denied. Despite the judge's decision, Habba seemed reluctant to accept it and tried objecting, prompting Kaplan to once again tell her to take a seat, Orden tweeted. To make matters worse, the reporter revealed that Kaplan ultimately had to remind Habba to stand up when addressing the courtroom, as she initially did so while seated.

The E. Jean Carroll defamation case proved to be a significant challenge for Alina Habba, as the awkward moments just kept pouring in throughout the January 17 hearing. Habba, who attended Widener University Commonwealth Law School, seemed to have a hard time following essential procedural rules, specifically regarding evidence.

In an attempt to demonstrate that Carroll was already experiencing online harassment prior to Donald Trump calling her a liar, Habba referenced the infamous "pathetic ugly old hag" tweet from 2019. The only problem was that she didn't formally log it as evidence to be used in court. "Guess what? You may not read from a document that's not in evidence," Senior U.S. District Judge Lewis Kaplan warned the confused lawyer and called for a recess. "We're going to take a break now until 3:30, during which you should refresh your memory about how it is you get a document into evidence," Kaplan told Habba (via New York Post).

Less than an hour later, Trump's lawyer seemed unsure about how to conduct a proper cross-examination. According to The New Republic, Habba asked Carroll about her Substack blog's popularity, to which Carroll confirmed it was indeed making her busy. Habba then attempted to inquire about Carroll's earnings from the platform, asking whether she made "a good amount of money," resulting in Kaplan swiftly cutting her off. "What's a good amount of money? Ms. Habba, this is Evidence 101," the jurist scolded her.

Proving that not all of her cringe-worthy moments are directly related to Donald Trump, Alina Habba once set herself up for failure when she willingly disclosed whether she'd rather look good or be smart. During a conversation on the "PBD Podcast" in January 2024, the topic of her appearance came up, with co-host Adam Sosnick asking the attorney "how much of [her] being an attractive, smart woman" influenced Trump's decision to hire her over a man, which he usually tends to do. "I don't think I'd be on TV or sitting here if I didn't look the way I look. I think I caught attention; I'm very honest about that. I don't mind," Habba candidly admitted, but emphasized that she wasn't hired because of her looks.

While the honest admission could have been the end of it, she went on to say, "I'll tell you something. Somebody said to me, 'Alina, would you rather be smart or pretty?' and I said, 'Oh, easy, pretty. I can fake being smart.'" While the podcast co-hosts laughed at her remark, Habba's beauty over brains comment totally backfired on social media, where users ruthlessly criticized the lawyer.

"Witness the audacious display of shamelessness! Clearly, she's vying for a role on the trashy 'Housewives of New Jersey,'" quipped one X user, while another penned, "She's going to cost [Trump] a fortune. This is not right-wing cable news."