On December 1, 2008, Sizemore was sent to jail after a Multnomah County judge found him in contempt of court for the fourth time in his long-running legal battle with two Oregon teachers unions. Multnomah County Circuit Judge Janice R. Wilson ordered Sizemore, who was not an officer of the corporation, jailed until he signed and filed federal and state tax forms that charitable organizations are required to complete to maintain their tax-exempt status. He was released the next day on December 2, 2008.
