The Money Woes Donald Trump Lawyer Alina Habba's Husband Has Faced

While Donald Trump's attorney, Alina Habba usually makes headlines thanks to her high-profile client, in November 2023, the attention turned to her own financial affairs. Granted, it seems as though the tax liens reportedly against her firm were misinterpreted (more on that in a sec). However, her husband's past tax issues haven't been quite as easy to dismiss.

To refresh, in November 2023, while defending Trump in his fraud case, an InTouch report noted that there were two liens against Habba's firm, Sandelands Eyet LLP, while her husband, Gregg Reuben had many more liens and warrants against him. In Habba's case, it appears the issue was slightly misconstrued. After all, per the report, the liens were filed against Sandelands Eyet LLP in 2021 and 2022 respectively. As noted on Habba's LinkedIn profile, she had stopped working there in 2020.

Reuben, on the other hand, has a fairly lengthy track record of not paying his taxes. The New York State website has a whopping 19 tax lien notices on file for him, dating from between 2015 and 2022. Over the years, Reuben has contested some of the liens, claiming that he should never have been made responsible for the liens. However, it seems as though the state of New York disagrees — at the time of writing, their website shows that none of the outstanding cases have been satisfied.

Gregg Reuben made a name for himself in the parking business and has had a pretty good track record over the years, with several parking companies to his name. However, as seen in New York State legal documents, things changed in around 2014. The docs show that Reuben grew concerned with the way his CFO was running their finances, fired him, and hired an accounting firm to look into the issues he was worried about. The firm's findings? While the CFO had filed returns, they had never been paid — and the money that should have been allocated to paying them was gone.

Soon enough, Reuben was in court for not paying those taxes. And, unfortunately for him, his reasoning that the CFO had hidden things from him didn't quite stand up in court. On the contrary, per court docs, the presiding judge pointed out that even if it wasn't his fault that the CFO had done some shady dealings, Reuben had consciously decided to not do routine checks to ensure everything was being paid.

Even with the judgment that Reuben was at fault, he appealed, on the grounds that while he'd been kept in the dark by the CFO, he had done what he could to intervene, as soon as he realized there was a problem. Even so, his appeal was denied.

A quick scroll through the New York State website's list of tax warrants against Gregg Reuben shows that while he's often listed alongside one of his companies, he's always listed as the person responsible for the account. As a 2020 Journal of Taxation article pointed out, that was a little on the ruthless side. However, Reuben's ownership had everything to do with that decision. 

Per the court documents from Reuben's appeal, he owned 99% of Alliance Parking in his personal capacity. The other 1%? Owned by Gregg Reuben Inc. Meaning, he owned the entire operation. For that reason, the Journal of Taxation article explained that he wouldn't even have qualified for the relief provisions set out in the 2018 New York Budget Bill. To have qualified for that, he would have needed to own under 50% of the company. Sure, he technically owned 1% ... but he would have needed to foot the bill based on the other 99%, anyway. In any case, the article also noted that if he had been granted relief, Reuben would still have been required to pay up part of what was owed. 

As we mentioned, at the time of this writing, Reuben has yet to settle any of the 19 warrants with his name on them. Given that he owes more than $2 million at this point, there's a chance settling up will take quite some time. TLDR: remember to double-check your taxes, peeps.