He accompanied Bishop Brennan to Craggy Island Parochial House to investigate a claim that an image of Bishop Brennan had been appearing on the skirting board of the house. This was really just an excuse to get Bishop Brennan to come to the house, in order for Ted Crilly to kick him up the arse. While he was there, Jessup confused Mrs. Doyle, by his frequent use of sarcasm. Mrs. Doyle, however, learned to ignore Jessup's sarcastic comments by doing the opposite of what he said.