Red Flags In Trump & Alina Habba's Relationship We Can't Ignore

There are plenty of weird things about Alina Habba's relationship with her boss, President Donald Trump, but certain aspects of their relationship dynamic present some pretty glaring red flags. For instance, Habba went from being Trump's personal attorney to one of his White House counselors to finally getting assigned the job of New Jersey's interim district attorney. But the thing is, Habba liked it in the White House, she didn't want to leave, and the outspoken lawyer told her boss exactly that (Trump ultimately convinced her that the lofty new position was just what she needed). Habba's new appointment begs the question as to why the president didn't offer her a more permanent role, though. 

She has declined to address this on multiple occasions, which hints that the tea is piping hot behind the scenes. While speaking to Real America's Voice, in March 2025, Habba admitted outright that she didn't even want the job. "I was so happy here [at the White House], and it was surprising," she said of the offer (via the Daily Beast). "I spoke to the president, and I just asked a lot of questions. It was his idea. He's like, 'I think you should do this' [...] And I said, I don't want to leave the White House. It makes me sad."

Unsurprisingly, though, Trump's former personal attorney eventually caved in to his demands. But whether that's really how things went down is debatable in itself. We can't help but wonder whether Trump publicly announced Habba's new role on Truth Social before she even formally accepted his offer, to force her hand. After all, that's how the art of the deal works in Trumpland, no?

When taking into account all the time, effort, and sacrifice Alina Habba has put into her relationship with Donald Trump, she should at least have had the option of saying no to a job she didn't want. But nobody promised it would be easy to keep the commander-in-chief happy, and sometimes sacrifices must be made. Habba made the ultimate sacrifice when she agreed to join the Trump White House for his second term, leaving her family behind to relocate to Washington, D.C. 

The new interim district attorney, who has been dubbed Trump's worst lawyer on multiple occasions, confirmed to the Daily Mail that her family fully supported her. "The decision to go to the White House was really a tough one, because I want to make sure that I had a purpose that would serve the country and Trump well," Habba admitted. While leaving her family behind was challenging, the attorney's husband, two kids, and step-son refused to hold her back: "They said, 'Mommy, you have to go. This is what you've been fighting for.' So, you know, my children are excited for me and that made the decision a lot easier."

Having gone to the trouble of moving to Washington only to be unceremoniously shipped back to New Jersey is probably not the thanks Habba was expecting from the president. But then again, Trump is a man who's known for doing unexpected things. His former personal attorney previously referred to the president as her "friend" in a teary speech at the 2024 Republican National Convention, before praising his "character, his kindness, and his commitment to saving this great country," (via The Independent). Only time will tell whether Habba continues to feel this way.

Friends don't let friends get fined $1 million. Unless you're Donald Trump, that is. Alina Habba had to dish out some cold, hard cash in 2023 after helping the president file a lawsuit against Hillary Clinton and some of her associates. U.S. District Judge Donald M. Middlebrooks decried them as "frivolous lawsuits" per NPR, and sanctioned the duo. Habba and Trump accused Clinton and her team of trying to undermine their 2016 presidential campaign by alleging that the president had allowed Russian interference to help secure his win, among other things. "He [Trump] is the mastermind of strategic abuse of the judicial process," Middlebrooks wrote in his order. 

He also noted how poorly executed the filing from Trump's team (aka Habba) was, deeming it unprofessional. "The Amended Complaint is a hodgepodge of disconnected, often immaterial events, followed by an implausible conclusion. This is a deliberate attempt to harass; to tell a story without regard to fact," Middlebrooks asserted (via Politico). Sadly, this was hardly Habba's first rodeo when it came to suffering a financial loss thanks to Trump's antics. The duo was previously fined $50,000 for bringing a lawsuit against Charles Dolan, who volunteered for Clinton's campaign. 

Middlebrooks sanctioned Trump and Habba in 2022, calling their suit against him a "two-hundred page political manifesto," (via CNN). Dolan had reportedly already told Habba and Trump that they had their facts wrong (they didn't even get his home address right), and Middlebrooks pointed out in his order that "the pleadings in this case contained factual allegations that were either knowingly false or made in reckless disregard for the truth." It's a wonder Habba continued working for Trump after all this drama, especially since these cases negatively affected her professional reputation.

Before Alina Habba left her family behind to work in the Trump White House, she was already spending most of her time by her boss's side. The controversial lawyer was busy making the rounds on the 2024 presidential campaign trail (Melania Trump, meanwhile, was nowhere to be seen) and after Donald Trump emerged as the victor on November 5, Habba wasn't home celebrating with her family — she was at Mar-a-Lago with him. In fact, there was rampant speculation at the time that Habba was more eager to join Trump in the White House than Melania.

Speaking to the Daily Mail after Donald announced that Habba would serve as a special counselor to the president, the attorney clarified that, while she was honored to land the job, she'd already been doing it for a long time in an unofficial capacity. "I've effectively been counselor to the president for the last three and a half years," Habba proudly confirmed. "I started as his attorney, and as time went on, I became something else. I became a spokesperson, then I became his general counsel to his PAC, and then I became a senior adviser to the campaign." 

As such, the staunch Trump loyalist reasoned, "So, for me, the road that I've been on is a natural progression to where I'm going." It seems Habba has been spending more time with Donald than her family for quite some time now. Perhaps sending her back to her home state to serve as the interim district attorney is the most friend-like thing her boss has done since they started collaborating. However, whether they will remain thick as thieves now that Habba no longer walks the hallowed White House halls remains to be seen.