As a teenager, Zachary was friend with Amelia Blake and Heather Barnes. At one point, Amelia stopped spending time with them, since she had joined the Circle, and he and Heather began to wonder why. On the night of the mysterious Boatyard Fire, Heather followed Amelia and returned left in a catatonic state, for which Zachary blamed the Circle. Amelia then departed town and Zachary remained the next years traveling as a fisherman and only coming back occasionally.
While in town, Zachary heard about Amelia's death and that her daughter Cassie had moved with her grandmother. He threatened her for being a witch like her mother but was stopped by Diana and left. In the Circle's lair , he scared Faye and there realised they had bound their Circle. Then, he confronted Charles about letting the children form a new Circle, knowing what had happened the last time and the two had a fight in which Zachary had the upper-hand. Instead of killing him, he left to kill one of the younger witches to destroy their bond. At the school dance, he chased and attacked Cassie, but the other members appeared and together created a small storm that knocked him out. When he woke up, he found himself at the back of Charles' car, where he and Dawn warned him that if he ever as much as look at their children again, he would suffer a fate worse than Heather's. To have an advantage on him .Dawn marked Zachary with her blood, therefore being able to sense if he would come back to Chance Harbor.