Former President Donald Trump has suffered through plenty of painful courtroom defeats during his lengthy career as one of America’s most litigious businessmen.

This time looks different. He’s now officially overdue to receive a downright brutal judicial ruling in a case that threatens to dismember his business empire, drain his cash reserves and drive him out of New York State as a businessman forever.

Manhattan Supreme Court Justice Aurthur Engoron blew through a self-imposed soft end-of-the-month deadline on Wednesday to deliver a judgment in the sweeping multi-million fraud lawsuit brought by the New York Attorney General Letitia James. Trump and his company have already been found liable, and are now just waiting to find out the size of the punishment. That decision could land at any moment, zapping Trump’s business like a thunderbolt when it does, in what could easily be the largest financial penalty of Trump’s life.

The New York Attorney General’s Office is seeking $370 million, along with a lifetime ban on Trump working in New York real estate or serving as an executive or director of a company based in the state. Judge Engoron declared Trump and his business liable for fraudulently overstating Trump’s wealth for financial gain in September. Now, the same judge bears sole responsibility for setting the penalty. A spokesperson for the court said Thursday that the ruling has been delayed until early to mid-February.

A $370 million fine would follow Trump’s $83 million defamation loss to writer E. Jean Carroll, in a lawsuit over Trump’s derisive denials of Carroll’s claim that Trump raped her in a New York department store bathroom in the 1990s.

Such mammoth judgements dwarf notable courtroom defeats Trump has faced in the past.

Trump’s company was fined only $1.6 million when it was found criminally liable in late 2022 for paying executives in off-the-books perks in what prosecutors branded an illegal scheme to minimize taxes.

When Trump settled three lawsuits brought against his Trump University real estate training program in November 2016, right after he was elected president, he paid out a total of $25 million. In that instance, the NY Attorney General’s office had accused the operation of fraud, saying the unaccredited, for-profit venture misled its customers by calling the business a “university.”