You’ve likely seen her on every major news network, the sharp-tongued attorney standing ten toes deep in the middle of a political firestorm. Alina Habba has become a household name, but while the cameras are fixed on her courtroom drama, there’s a much quieter, high-stakes game being played by the man standing just off-camera. That’s her husband, Gregg Reuben.
He isn't just "the husband." Reuben is a heavyweight in a world most of us only think about when we’re frustrated and looking for a spot in Manhattan: the parking industry. But their relationship isn't just about business and legal briefs. It’s a story of a whirlwind 2020 marriage, a massive blended family, and some eye-popping financial headlines that have people whispering from Bedminster to Mar-a-Lago.
Who is Gregg Reuben?
Basically, if you’ve parked a car in New York City lately, there’s a decent chance you’ve handed money to one of Gregg Reuben’s companies. He’s the CEO of Centerpark, a firm that doesn’t just manage garages; it repositions them as high-value real estate assets.
Reuben is a Harvard Business School grad who’s been in the game since the early 90s. We’re talking over 25 years of experience. He started out with a company called Autofair America in Los Angeles, then bounced through executive roles at giants like ABM Industries and LAZ Parking. By the time he founded Centerpark in 2017, he was already a veteran. Honestly, the guy turned parking into a science, even winning a "Best Business Strategy" award at Harvard for his model.
The Whirlwind Romance of 2020
The timing of their relationship has always raised a few eyebrows. Alina Habba was previously married to another attorney, Matthew Eyet. They divorced in late 2019. Then, 2020 hit. While the rest of the world was figuring out Zoom, Habba and Reuben were tying the knot in a private ceremony.
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Some internet sleuths pointed to an Instagram post Habba shared in 2022, showing a massive bouquet for their first-date anniversary. If you do the math—which people on Twitter love to do—the dates seem to overlap with her previous separation. Regardless of the timeline, they’ve built a tight-knit unit. It’s a "yours, mine, and ours" situation. Reuben has a son, Parker, from a previous relationship, and Habba has two children, Chloe and Luke. Together, they call them their "three nuggets."
The $100 Million Ambition Meets Tax Liens
Here is where it gets a little messy. Professionally, Reuben is on fire. Centerpark recently secured a reported $100 million investment to expand across New York. He’s obsessed with "gateway cities"—those economic anchors like NYC that never sleep.
But then there’s the debt. In late 2023, reports surfaced that the couple was facing significant tax trouble. We’re talking over $1 million in combined tax liens. Most of that weight actually sits on Reuben’s side of the ledger, stemming from business liens and unpaid warrants dating back to 2016. It’s a strange contrast: a man managing $100 million in assets while the IRS is knocking on the door.
Why the Congestion Pricing Fight Matters
Lately, the connection between Gregg Reuben and Alina Habba has moved from the gossip columns to the political sphere. Habba has been a vocal opponent of New York’s congestion pricing plan.
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Why does that matter?
- Direct Conflict: Centerpark owns nearly 30 garages in Manhattan.
- The Zone: A huge chunk of those garages are located right inside the proposed congestion zone.
- The Logic: If fewer people drive into the city because of the toll, fewer people pay Reuben for a parking spot.
Critics have been quick to point out that Habba’s "policy" stance looks a lot like a family business defense. Ethical watchdogs have had a field day with it, especially since Habba once served as general counsel for Centerpark itself.
The Diamond Ring Lawsuit
If the tax liens weren't enough drama, there’s the engagement ring. Reuben actually sued a Manhattan jeweler, Allurez, back in 2021. He claimed he paid $93,000 for a seven-carat diamond ring that was later appraised at just $15,000.
Imagine trying to surprise your powerhouse lawyer girlfriend and finding out you got scammed on the rock. He sued for the full price plus $500,000 in damages. It’s just one more example of how their private life constantly mirrors the high-stakes litigation Habba handles for her most famous client.
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What Most People Get Wrong
People tend to see Gregg Reuben as just a background character in the Trump legal saga. That’s a mistake. He’s a tactical businessman who understands urban infrastructure better than most. He’s also deeply involved in the Jewish community, serving on the boards of the Henry Kaufmann Campgrounds and Lost Tribe Esports.
The reality is that their lives are deeply intertwined with the New York power structure. They aren't just a lawyer and a businessman; they are a modern power couple navigating the intersection of real estate, law, and national politics.
Actionable Insights for Following the Story
If you're trying to keep up with the moving pieces of the Gregg Reuben and Alina Habba dynamic, keep your eyes on these three areas:
- Court Filings: Watch the resolution of the tax liens. If Reuben’s business expansion continues, these debts should, in theory, be cleared. If they aren't, it signals deeper cash flow issues.
- Congestion Pricing Rulings: As the White House and NYC battle over tolls, look for Habba’s influence. Her husband’s business depends on those cars staying on the road.
- Real Estate Acquisitions: Centerpark is currently in "buy" mode. Watch for them to acquire smaller, family-owned garages in the tri-state area. This is how Reuben is building his "gateway city" empire.
The story isn't just about who they are today, but how they’ve positioned themselves for a very loud future in the public eye.