Wolf also worked full-time as a lawyer for the Chicago law firm Holstein, Mack and Klein from 1982 until 1987. He decided to leave the law in 1987 to focus full-time on broadcasting. "When I was an attorney on the radio, that was crazy," he told the Chicago Tribune in 1991. "Trying to explain to a judge that you need a recess to do a sportscast...the two jobs didn't dovetail at all. It was difficult to do both jobs well. So when the TV opportunity opened up, I just seized it."