The former head of a prominent New York City real estate broker must finally pay the government millions in taxes he dodged starting more than a decade ago.

A bankruptcy judge ordered Jeff Winick to pay roughly $9M to the Internal Revenue Service for income tax he failed to pay between 2012 and 2016, Bloomberg Law first reported.

Winick, the founder and longtime CEO of retail specialist Winick Realty Group, filed for bankruptcy in 2020, claiming roughly $10M in liabilities and $500K in assets. The IRS sued him later that year, claiming he had fraudulently transferred assets to his family and business partners and lived a lavish lifestyle while evading income taxes.

Winick lost more than $12M from gambling in the years leading up to his bankruptcy, which he claimed was "non-volitional" spending due to a gambling addiction.

U.S. Bankruptcy Judge Philip Bentley didn't buy that, pointing to other years Winick gambled and still paid taxes, as well as his luxury lifestyle: paying $180K in annual rent for a Southampton vacation home, dozens of international trips, and shopping sprees for his ex-wife, ex-girlfriend and daughter.

The former retail mogul took home millions in commissions but instructed his company's accountants to only withhold taxes from his salary. He also transferred shares in his businesses and properties he owned to his daughter for no consideration, which the IRS pointed to as a likely tax dodge.

In his 46-page ruling, Bentley wrote that Winick's tax filing year after year was “an outright fabrication.” Winick did pay nearly $2M in taxes between 2014 and 2020 — “a significant achievement,” Bentley wrote.

Winick argued during the case that he planned to pay the taxes if he got a big win at the casino or had a big year in business, but that never happened.

“A hope of this sort is little different from that of many Ponzi artists and other fraudsters who rationalize their wrongs by telling themselves they will one day repay their victims,” the judge wrote. “Such hopes are no excuse for fraud—and in this case, any hopes and good intentions Winick may have had are no excuse for his repeated and willful choice to gamble with the government’s money and then flout the tax laws and lie to the IRS to prevent it from taking steps to collect his back taxes.”

A year after the bankruptcy filing, Winick's majority stake in his business was auctioned off to company insiders. The company rebranded last year as RTL, with Steven Baker, one of the company's owners, named as CEO, CoStar reported.