A defense lawyer for Michael Flynn on Wednesday formally demanded the disqualification of U.S. District Judge Emmet Sullivan of the District of Columbia from the former Trump national security adviser’s case, arguing that the longtime federal judge has shown himself to be “irreparably biased” against Flynn in the three years since he admitted to lying to the FBI about his communications with the Russian ambassador to the U.S.

Flynn’s lead defense lawyer, Sidney Powell, said Sullivan’s “contempt and disdain for the defense was palpable” at a hearing last week, where the Washington judge inquired about the circumstances surrounding the Justice Department’s unusual move to abandon a prosecution in which the onetime Trump adviser twice pleaded guilty.