Jack bought half the "Spectator" to keep them from running a story about him. He attempted to blackmail co-partner Diana Colville into selling her other half. Originally she refused, but he later got his hands on it. The "Spectator" is where Jack met college student Jennifer Horton. She was trying to help a homeless pregnant girl named Sally, and the two pretended to be married to give the baby a home. Their fantasy love turned into a real thing, but the return of Jennifer's childhood sweetheart, Emilio, put a wedge between them. When Melissa returned to town, she tried to push Jennifer and Emilio together, believing Jack had not changed his ways. Jack allowed this to happen believing he was unworthy of Jennifer all the while his actions spoke for him as he kept throwing monkey wrenches into Jennifer and Emilio's 'relationship'. Going so far as to kidnap Jennifer on her wedding day to Emilio.