Alina Habba's Relationship With Trump Just Keeps Getting Weirder

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Donald Trump is renowned for his fickle friendships and broken bonds. Sometimes, it seems like he gets through friends faster than a can of hairspray. But Donald's relationship with his attorney, Alina Habba, has proven enduring, at least so far. Still, it's far from your regular client-attorney arrangement.

Habba and Trump spend an inordinate amount of time together, so much so that gossip of an affair sparked when she first arrived on the scene. X, formerly Twitter, roasted Habba as a Melania Trump wannabe, and rumors spread of a feud between the two. However, there are plenty of signs that Habba and Melania are actually closer than we think — adding to the strangeness of her bond with The Donald.

They've become so close that speculation swirled she was in line to be his administration's press secretary. A strange appointment, even by Trump standards. Habba shot the conjecture down, though. "While I am flattered by the support and speculation, the role of Press Secretary is not a role I am considering," she shared on X. "Although I love screaming from a podium, I will be better served in other capacities." Well, job change or no job change, Trump and Habba's relationship is still weird, and it just keeps getting weirder.

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Alina Habba seems to look more and more like Melania Trump by the day. She's added extensions, layers, and honey-blonde highlights to her sleeker and straighter hair. Habba's eyebrows are darker, thicker, and less arched, and her wardrobe is more tailored, simple, and monochrome. The transformation hasn't gone unnoticed, with some speculating that Habba is morphing into Melania with the hope of becoming the fourth Mrs. Trump.

"I don't know if Habba is trying to look like Melania or if it's accidental...but, it is interesting to see the similarities. It's like watching someone's subconscious desires play out in real time. The hair, the outfits.... it's like she's channeling Melania without even realizing it," a commenter posted on X. Conjecture was further fueled by a photo of Trump and Habba on his private jet.

"Is Habba the Melanie stand-in we saw the last 6 years? Cadespite consistently losingn't imagine Melanie would like this picture very much. Will Habba be wife #4?" a speculator asked. "Honestly, it's a toss-up. Either she studied Melania's look like it was part of the bar exam, or Trump just has a "must resemble my wife'" hiring policy. Coincidence? I think not! Lol," another chimed in.

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Donald Trump is vocal about his disdain for people he perceives as failures. According to The Atlantic, he disparaged soldiers who died in combat and attempted to have disabled veterans banned from military parades. "Why should I go to that cemetery? It's filled with losers," a source claimed Trump said before canceling a 2018 scheduled visit to a US military cemetery near Paris, France.

He's all about the victories, no matter the cost. "We will have so much winning that, believe me, you may get bored with the winning," Trump vowed in September 2016. He's so obsessed with not losing that he even insists he won the 2020 election despite overwhelming evidence to the contrary. So, it's weird that he retains the legal services of Alina Habba, given she represented him in the E. Jean Carroll defamation case that resulted in an $83 million loss. She was also part of the team that lost Trump's New York fraud trial, landing him with a $454 million civil judgment.

However, Habba remains integral to Trump's trusted circle of attorneys. She acted as his legal advisor and spoke on his behalf during his New York hush money trial. "I plan, for the next six weeks, to truly just be spitting the truth and giving people facts they may not be hearing while he's in court," she announced on "The Benny Show" in April 2024 while somehow maintaining a straight face.

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Alina Habba works on Donald Trump's civil cases, so her legal expertise wasn't required during his New York Stormy Daniels hush money criminal trial. Still, that didn't stop her from being in the courtroom — and outside the courtroom — ranting on behalf of Trump at every opportunity.

"What I have seen is an absolute demise of American judicial system.....I can't believe what I've seen for the past two days in that courtroom," Habba told Fox News' Sean Hannity on the day of Stormy Daniels' cross-examination. "They did not care; they went ahead and put salacious information that was frankly false. We know that from words that were said prior to this trial. And now we're sitting here scratching our heads, wondering where taxpayer dollars are going."

Sadly for Habba, her defense was as unsuccessful as her Trump-trial track record. Still, at least this time, she didn't risk landing behind bars herself. Following a particularly heated exchange during the E. Jean Carroll defamation trial in January 2024, Habba was threatened with jail time if she didn't tone things down. Habba took objection to U.S. District Court Judge Lewis Kaplan's ruling that copies of X messages that hadn't previously been included in evidence couldn't be presented in court, and she angrily argued over him as he spoke. "You are on the verge of spending some time in the lockup. Now, sit down," Kaplan ordered her, The Hill reported.

Given the amount of time Alina Habba spends with Donald Trump, it's little surprise that the couple sparked rumors of an affair. The attorney appears to have become a Melania Trump stand-in and is regularly photographed by his side. In addition to Melania being MIA, Habba's husband, Gregg Reuben, is also usually nowhere to be seen, making for an unusual spousal situation.

Little is known about Reuben. Unlike his high-profile wife, he prefers to stay out of the limelight, sitting back and allowing Habba to bask in the media glow. However, Reuben has a personal travel blog describing himself as "a highly successful entrepreneur who lives and works in New York City." Well, that sounds familiar.

"Reuben is the proud owner of CenterPark, a parking management company that is committed to providing eco-friendly parking options across the tri-state area," he writes of his career, sharing that he knew from a young age that the world of parking management was his calling in life. Still, it's not all work and no play for Reuben. He's also passionate about traveling and loves to give back to the community. The businessman sits on the board of The Lost Tribe Esport, "an organization that works to bring Jewish youth together through gaming."

It isn't just Alina Habba who's been welcomed into Donald Trump's inner sanctum with open arms. Her friends have also come along for the ride — specifically, her BFF Siggy Flicker. The former "Real Housewives of New Jersey" star has become a frequent flier at Mar-a-Lago and is often snapped enjoying a few rounds on the golf course.

Habba and Flicker were by Trump's side on the night of his presidential election victory. Christian country artist Natasha Owens posted a clip of the two women serenading The Donald to her song "Trump Won." In the video, they're seen singing and dancing excitedly in their chairs as Trump taps on the table in time with the music.

The MAGA loyalists went wild with appreciation. "Such smart, beautiful women he surrounds himself with!... let's make America great again!" one wrote in the MailOnline comments section. "Man, Conservative women are so much prettier than the purple haired angry liberal women," another claimed. "Our President, Donald J. Trump surrounds himself with beautiful women. Just look at his glamour's wife, Melania," a third gushed.