In 2012, Judge Benson denied convicted felon Dewey MacKay's request to remain free pending appeal of his guilty verdict. However, Judge Benson, without objection from the Prosecution, did allow MacKay to remain free pending appeal of Benson's denial. MacKay was convicted in August, 2011 of 40 counts related to illegally prescribing pain killers. Between 2005-2009 MacKay prescribed over 3.5 million pills of opiate painkillers. During the appeal hearing, Benson said that the jury's verdict had sufficient evidence, but expressed sympathy towards MacKay and his family and stating that the 20-year mandatory minimum sentence issued by Benson was "too long'. "It's very easy to get almost teary-eyed over the health issue alone," Benson said. "This is so hard for people who love and admire and respect this man, which is many." Benson told MacKay's family that he "can't even imagine" the "nightmare" they are going through. "It must be like a black cloud," he said. He said that America's jury system is not perfect, but added that jurors in MacKay's case performed their jobs diligently. MacKay's attorney's used his failing health and large numbers of prescription drugs he takes as reasons why MacKay should stay out of prison.
