Rudy Giuliani, a former New York City mayor and lawyer to Donald Trump, has been held in contempt of court for failing to pay damages as part of a defamation lawsuit.
A judge found that Giuliani defamed two Georgia election workers over false claims they tampered with votes during the 2020 presidential election. He was ordered to pay $148m (£116m).
The first transfer of $11m was originally scheduled to take place in October, as a down payment to poll workers Ruby Freeman and her daughter Wandrea Moss.
Giuliani argued that he had largely complied with the judgement, but a New York City judge ruled Monday that he "wilfully violated an unambiguous order of the court".
Lawyers for the women have said they have received only a fraction of the assets.
Freeman and Moss filed a lawsuit against Giuliani in 2021, accusing him of destroying their reputations and arguing that his statements led to a torrent of abuse.
The long-time ally of President-elect Donald Trump had made repeated false claims that a surveillance video of the pair showed evidence of ballot tampering. He claimed they were passing USB drives back and forth, when in fact they were passing a box of mints.
He later conceded he made defamatory statements, and a jury ordered him to pay $73m in compensation and $75m as punishment.
Giuliani filed for bankruptcy shortly after the decision, but the case was dismissed, leaving Trump's former lawyer without protection from creditors.
A judge later ordered him to turn over his Manhattan apartment, more than two dozen watches, a jersey signed by former New York Yankees centre fielder Joe DiMaggio, and other valuables to the two Georgia election workers as part of the defamation penalty.
During a two-day hearing, Giuliani said the whereabouts of some of the items, such as the DiMaggio jersey, are unknown.
US District Judge Lewis Liman said he would decide on punishment at a later date.
Giuliani faces a further court hearing over whether his Yankees World Series rings and his Florida home should be handed over to help pay his debt to the election workers.
He has also been indicted in Georgia and Arizona on criminal charges related to attempts to overthrow the result of the 2020 election.
Giuliani, a Republican, was first elected mayor of New York City in 1993 and was in charge at the time of the 2001 attacks on the World Trade Center. In 2008 he ran for president and later became a Trump advisor.
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