After 18 years working for WFLD-TV, Wolf was terminated in February 2006. The reasons for his firing were never made entirely clear, but local media provided two explanations. One was that Wolf's contract was too rich for the station. The other reason involved a pair of incidents that had occurred over the previous six months. The first incident, in September 2005, involved WFLD suspending Wolf for three days after an awkward on-air appearance involving then-WGCI-FM radio personality "Crazy Howard" McGee, who apparently while appearing on WFLD had made a crude, below-the-waist gesture. Wolf turned around and denigrated the gesture during his sports segment, leading to an off-camera incident with a producer. The second incident, at the Chicago Auto Show in February 2006, involving a taped off-beat segment (which never aired) involving Wolf interviewing a man standing outside of the Auto Show in front of his own car. Wolf apparently asked if he could "key" the car, and the man dared him to do so. When Wolf did so, the man became enraged.