Fennimore Winchester is the sheriff for Conklin County, Missouri where his mother is also the local judge J. T. Winchester. After Superintendent Chalmers accidentally crashed Agnes Skinner's Buick, Winchester suddenly appeared, and detained them until the trial. After the judge gave Skinner her car, which was dented by a telephone pole, Skinner was apparently driving in the county that Fennimore presides over, and was caught with the dent. Skinner was most likely arrested for the damages, even though he was seen at the convention in Cincinnati.