Trump's Worst Lawyer Has Had Some Serious Financial Troubles

Alina Habba might have the MAGA look down pat, but she could be in danger of running out of the money required to keep it up. It turns out that Habba and her husband, Gregg Reuben, are in dire straits financially. At least, they were in 2023, when In Touch Weekly revealed that the couple collectively owed more than $1 million in liens and warrants. This sum was made up of some money Habba's firm owed in tax liens alongside additional debt from her husband's LLCs. If you were wondering how bad this is, well, it's pretty serious. According to real estate and bankruptcy expert Jeremy Wallace, "A lien is filed in a way that is attached to anything you own [and can be] real estate or personal property. Theoretically, they can come and raid your house and take your Rolexes." Donald Trump's former lawyer better hold on tight to that overpriced engagement ring of hers (which notably also got Habba's husband involved in a messy legal battle). 

It's entirely possible that the couple has managed to better their financial situation in the time since, but when taking into account that Habba got fined about $1 million by a Florida judge in 2023 along with her beloved boss for what was deemed a "completely frivolous" lawsuit against Hillary Clinton and other key political players, per NPR, it's unlikely. Even more so when one takes into account the legal trouble that the controversial attorney found herself in after she overplayed her hand as New Jersey's interim district attorney, when Habba infamously had Mayor Ras Baraka arrested outside a U.S. Immigration and Customs Enforcement detention facility in May 2025. Baraka retaliated by suing Habba for malicious prosecution, demanding that she pay for the damage caused to his reputation. 

There have been several red flags in Alina Habba and Donald Trump's relationship that we can't ignore. Likewise, there were also some pretty glaring signs that the president was trying to distance himself from his former attorney when he, quite frankly, demoted Habba from her high-profile job as a presidential counsellor to New Jersey's interim district attorney. Note the term "interim." It's not clear why Trump didn't make it a permanent appointment, though. Perhaps he wanted to make it easier to oust Habba from her position once he no longer deems her worthy of his cause. 

It's no secret that the real estate mogul is allergic to poor people (Habba is still far from destitute, obviously). In 2017, Trump made a controversial statement while attempting to defend his wealthy cabinet members. "I love all people, rich or poor. But in those particular positions, I just don't want a poor person," he reasoned (via CNBC). It seems this continues to hold true today. Moreover, while she was making an appearance on "Real America's Voice," Habba admitted that she didn't want the district attorney job in the first place. 

"I was so happy here [at the White House], and it was surprising," the lawyer confessed (via the Daily Beast), later adding, "And I said [to the president], I don't want to leave the White House. It makes me sad." She remains hurt since it doesn't seem like Trump is planning to bring her back to the White House any time soon. Perhaps the president is finally paying attention to all the times Habba has been called out for being Trump's worst lawyer.