Caulfield was the Sheriff in Fredericksburg, Virginia. In 1980, Caulfield was investigating the disappearances and murders of several teenage girls in the area. When the killings suddenly stopped in December 1980, he became depressed and started drinking, until he was eventually asked to retire.
In 2007, the murders resume, with the same M.O. as the ones 20 years earlier. The BAU ask who had been previously in charge of the investigation, and Caulfield is brought in to assist them. During this time, Caulfield and Agent Rossi share their similar cases of longtime unsolved murders. They begin asking if anyone had died or moved away around the time the murders stopped, and he tells them of Robert Wilkinson. They go to his old house, where they find his widow, Mary. They enter Robert's barn and see the somewhat fresh blood on the ax and chopping block. They ask Mary where her son is, and she directs them to Chrissy Wilkinson. While the BAU find the abducted girls up in the mountain, Caulfield and the others search for Charlie. After Chrissy shoots Charlie, Caulfield is both happy and sad that he finds out who was responsible, but 27 years late. He asks Rossi how long ago the Galen murders occurred, and Rossi tells him 21 years had passed. He then replies, "Don't let it get to 22."