Thursday's ruling by Court of Queen's Bench Justice Chris Martin is the latest legal setback for Alexander Chapman, who went public in 2010 with accusations of being sexually harassed by Justice Lori Douglas and her husband, Jack King, in 2003.
King had been Chapman's divorce lawyer. He has admitted to giving nude photos of Douglas, a fellow lawyer at the time, to Chapman in an attempt to convince him to have sex with her, but said he acted without Douglas's knowledge.
Chapman complained to King's law firm soon afterward. That led to a settlement that saw King pay Chapman $25,000 on the condition he return all photos and never publicly discuss what had happened.
Chapman has admitted to breaking that deal and has said he had to go public because he continues to be haunted by what happened.
Because he broke the confidentiality clause and spread the photos, Chapman must now repay the money he was given.
"We know that Mr. Chapman went to the media and provided to the media the very same documents (he had agreed to return)," King's lawyer, Bill Gange, told court Thursday.
Chapman will also have to pay King's legal expenses which could top $10,000, although the exact amount has yet to be determined. Neither Chapman nor his lawyer showed up for the decision.
The controversy over the nude photos, some of which show Douglas in bondage gear and performing sex acts, has led to a public inquiry. The Canadian Judicial Council is holding hearings this summer to determine whether Douglas should be removed from the bench.
Douglas has denied any wrongdoing and has said she should not be penalized for her husband's actions. The photos remain on the Internet.
Chapman has already lost other legal actions. In 2010, he filed separate lawsuits against Douglas, King and the law firm where they worked. He soon dropped the claims against the law firm and Douglas due to a lack of evidence. His lawsuit against King was dismissed when a judge ruled the matter was resolved by the 2003 settlement agreement.