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".
Mr Giuliani, 79, said earlier this year that he was having financial difficulties because of his increasing legal fees and expenses.
Last week, an eight-person jury ordered him to pay $20m to Georgia poll workers Ruby Freeman and her daughter Wandrea "Shaye" Moss.
The pair said Mr Giuliani's false claim that they tampered with votes had a traumatising impact on their lives. Ms Freeman said she would "always have to be careful" because of lingering fears she might be recognised publicly.
Ms Freeman and Ms Moss were also awarded more than $16m each for emotional distress. Another payment of $75m in punitive damages was ordered to be split between them.
Addressing reporters outside the court after he was ordered to pay the sum, Mr Giuliani said: "I don't regret a damn thing."
On Wednesday, a judge ordered him to start paying the two women immediately and expressed concern he might not comply with the judgement.
It is unclear how the bankruptcy declaration will impact on the payments, but US bankruptcy law does not allow the dissolution of debts stemming from "wilful and malicious injury" inflicted on another party.
The bankruptcy filing lists nearly 20 creditors, including Ms Freeman, Ms Moss and Hunter Biden who sued him in September.
Other creditors include the Internal Revenue Service (IRS), which he owes more than $700,000 in income tax, and two voting software companies that sued him over his false claims of election fraud.
A law firm that previously represented Mr Giuliani, Davidoff Hutcher & Citron LLP, is also included. The firm sued Mr Giuliani for $1.4m in unpaid legal fees in September.
Mr Giuliani still faces an indictment in Georgia on racketeering and conspiracy charges as well as a $10m lawsuit by a former business associate over sexual harassment claims.
