In 1985, Tad's beloved grandmother Kate dies. He later finds out that Bob is lying about his condition, leading to Hillary and Bob's divorce. She and Tad marry in 1986. Hillary discovers con artist Wade Matthews (Christopher Holder) has evil intentions toward her stepmother, Phoebe, and that Tad knows but is keeping it secret under threat of blackmail. Between the stress of this revelation and Hillary's focus on law school, Tad succumbs to the attentions of a lounge singer, who is revealed to be Adam Chandler's estranged daughter, Skye Chandler (Antoinette Byron, then Robin Christopher) despite desperate attempts to gain Hillary's forgiveness after she finds out about Tad's infidelity, she ends their marriage. A broken-hearted Tad leaves Pine Valley in 1986 to make a fresh start.