Caleb's mother, Becky Hilson brought him to the medical practice the day before Planksgiving in 2011 because he was experiencing a great deal of itching. However, Dr. Zoe Hart found no rash and all vital signs looking well, so gave him an antihistamine and assumed it would clear up.
Later the same day, Caleb and his mother were back, this time asking to see Dr. Breeland, and with joint pain, dizziness, coughing, and continual itchiness. Determined to decipher Caleb's symptoms, and to reach her patient quota for the billing quarter, Zoe Hart used her friends Addie Pickett and Lavon Hayes to do some reconnaissance, to be her "eyes and ears" since Brick had removed her from the exam room. When it was determined Caleb had salt residue on his body, likely from saltwater, Zoe pressures Caleb to tell the truth, that if he didn't, he would only get sicker, after which Zoe revealed he had Decompression Sickness, often reffered to as "The Bends" by professional divers, and Caleb was rushed to be treated at Mobile Presbyterian Hospital.
Caleb later confessed to stealing his older brother, Nate Hilson's diving gear and diving on his own, looking for pirate treasure from the Planksgiving legends, and he was doing it so that his parents wouldn't have to sell Nate's Hardware, his father wouldn't have to leave to look for work, and his family could stay together.