At an unknown point prior to or after the attack on the Mary Ann 20 years previous, the Sea Hag discovered Professor Cringly and enslaved him for her own nefarious purposes, imprisoning him on Plunder Island, where she would subject him to many horrors. Eventually, fortune would smile kindly upon the fearful professor as he was able to escape his imprisonment and eventually came to meet Bill Barnacle at sea, who would help him make his way to the port town of Sweethaven in hopes that Cringly would tell him the location of Plunder Island, where countless treasures were hidden.
Shortly after arriving to port with Bill Barnacle, Cringly grew tremendously paranoid after Barnacle left him for a brief moment to see his old friend Popeye. Fearing that the Sea Hag would get him now that he was alone, Cringly became desperate and to avoid her wrath, he purposely got himself arrested by throwing a brick through a window. He would then reunite with Bill in jail, since Bill and Popeye had been arrested for roughhousing at Mike's Place another night. The trio then broke out of jail with sheer brute force and made their way to Popeye's newly acquired restaurant to plan out their trip to Plunder Island, while Wimpy took care of the terrified Cringly in hopes to calm the Professor's nerves with a gentle story. However, Cringly's terror proved too strong and he eventually ran up to the roof in fear, only for his fears to become well-founded as he realized it was the night of the Red Moon, an omen caused by the Sea Hag's cursed ship, the Black Barnacle, and could only mean that the Sea Hag was most definitely in town. Wimpy however convinced him to come down and tried to get him to sleep, but his efforts were put to a quick stop as he saw a towering monstrous creature looming behind him, who easily subdued Wimpy and whisked the horrified Cringly away into the night and dragged him into the sea, to later awaken in the brig of the Black Barnacle and be reunited with his evil former mistress, the Sea Hag.