Billionaire Michael Cherney took a hit to both his wallet and his reputation on Friday, when a state court judge in Manhattan ruled that the businessman owes a half-billion dollars to longtime foe Alexander Gliklad. Siding with lawyers at Winston & Strawn, the judge ruled that Cherney conjured a flimsy defense and dragged his feet during discovery.

In a short but punchy decision, New York Supreme Court justice Melvin Schweitzer agreed with Gliklad that a promissory note entitles him to a $270 million payment from Cherney—an amount that’s now swelled to about $503 million with interest. Cherney claimed that there were errors in the execution of the promissory note, which was signed in Russian in a hotel room in Vienna following a boozy evening a decade ago, and that the note was supposed to state that Cherney’s the one entitled to payment.

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