Rudy Giuliani, a longtime associate of former President Donald Trump, has filed for bankruptcy just days after he was ordered to pay $148m (£116m) in a defamation case.
He was ordered to pay the sum after a judge found he defamed two Georgia election workers over false claims they tampered with votes in 2020.
The filing shows he owes millions of dollars in legal fees and unpaid taxes.
A spokesman said the move should "be a surprise to no-one".
In a statement, the spokesman for Mr Giuliani, Ted Goodman, said "no person could have reasonably believed that [Mr Giuliani] would be able to pay such a high punitive amount".
He added that Thursday's bankruptcy filing in New York would give Mr Giuliani the "opportunity and time to pursue an appeal, while providing transparency for his finances under the supervision of the bankruptcy court".
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