Alina Habba, the outspoken former attorney for Donald Trump, is once again in the spotlight—but this time, it’s not just for her controversial comments or political affiliations. Recent reports reveal that she and her husband, businessman Gregg Reuben, are entangled in significant financial trouble, with over $1.5 million owed in tax warrants and business liens.
According to InTouch Weekly, most of their debt stems from Reuben’s unpaid tax obligations in New York, amounting to approximately $800,000, coupled with more than $770,000 in business liens. Despite a combined estimated net worth ranging between $2 to $5 million, the couple now faces scrutiny for their mounting liabilities, drawing even more attention as Habba transitions into a prominent role within Trump’s administration.
Who Is Gregg Reuben?
Gregg Reuben is not new to the business world. With degrees from UCLA and Harvard, he has had a long and diverse career in the parking management and real estate investment industries. Years before his marriage to Habba, Reuben made a name for himself by founding Centerpark, a New York City-based company focused on eco-friendly parking solutions across New York, New Jersey, and Connecticut.
Reuben’s impressive resume also includes executive leadership roles at several major firms. He served as the President of Autofair America, Inc. from 1991 to 1997 before selling the company. He later became the Vice President of Mergers and Acquisitions for ABM Industries, one of the largest parking management companies in the U.S.
His leadership journey continued with positions as Vice President and Regional Partner for LAZ Parking, CEO of Alliance Parking, and Vice President and Managing Director of SP+, another major name in the parking sector.
Despite this track record, Reuben is now making headlines for less favorable reasons—specifically, the financial weight of tax warrants and legal filings against his business operations.
Alina Habba: From Legal Spotlight to Political Arena
Alina Habba, 40, rose to national attention as a passionate and aggressive legal voice defending former President Donald Trump. She previously served as his lead attorney in several high-profile cases, which she frequently characterized as political “witch hunts.”
However, Habba recently stepped down from her legal role, reportedly to focus on “significant projects” within Trump’s camp. She has been appointed as Counselor to the President in Trump’s re-election campaign and is now tasked with a more strategic, behind-the-scenes position—though she’s still making waves in public appearances.
During a recent Fox News interview, Habba defended Trump’s controversial comments about diversity, equity, and inclusion (DEI) hires following a tragic plane crash. Responding to criticism from Illinois Governor J.B. Pritzker, who called Trump “unfit to lead during moments of crisis,” Habba said, “We cannot have sloppy, lazy, and inappropriate hires because American people are going to suffer and die.”
She doubled down, clarifying Trump’s comments by suggesting that DEI initiatives prioritize race over merit. “All he’s saying is we need the best of the best,” Habba explained. “America has the best of the best.”
Her remarks quickly sparked backlash online, with political commentators and everyday users alike criticizing the rhetoric. On Threads, journalist Aaron Rupar responded sarcastically, “She is right. Trump should not be President.”
Others joined in with equally biting commentary, highlighting the irony in Habba’s critique while defending a former administration many consider emblematic of favoritism and controversy.
The Financial Picture: A Net Worth in Question
Though the couple’s estimated combined net worth is listed between $2 to $5 million, the recent revelations surrounding their tax and legal obligations paint a murkier financial picture. Reuben’s $800,000 in unpaid New York taxes and additional liens indicate significant fiscal challenges that could threaten both their personal wealth and public credibility.
Habba and Reuben have not publicly addressed the growing financial issues. Still, their silence amid increasing media attention is raising eyebrows, especially as Habba takes on a more prominent role in Trump’s political future.
The couple’s lifestyle and financial management are now under scrutiny, and questions about their long-term solvency continue to swirl.
Personal Life and Public Fallout
Though Alina Habba has been a vocal figure in political commentary, her personal life was largely kept private until recently. Her marriage to Gregg Reuben and their growing visibility as a couple aligned with Donald Trump has added a new layer of public interest.
Reuben’s business activities and financial liabilities may not only reflect on his own credibility but may also impact Habba’s future in political consulting and legal analysis. With Habba now embedded in Trump’s campaign strategy and narrative, the stakes are higher than ever—not just for her career but for their reputation as a couple.
Conclusion
Alina Habba and Gregg Reuben’s current challenges highlight the blurred lines between public service, political ambition, and private financial responsibility. As Reuben faces legal and financial scrutiny and Habba continues to spark national debate with her unapologetic political stances, their lives remain deeply entwined with the chaos and controversy of modern political discourse.
Whether they weather the storm or face more serious consequences remains to be seen. What is clear, however, is that the spotlight on Alina Habba is no longer limited to her courtroom strategies—it now extends to her household’s financial future, her husband’s business dealings, and the complex intersection of money, politics, and influence.
