The days before the arrest of Jessie Bains, he learned that Kathy was doing drugs getting them at school. Meanwhile he became an alcoholic which brought his marriage on the rocks and his wife was ready to leave him.
Cobb backed up Sonny during the arrest of Jason Taselli.
Later that day, Kathy fell in a coma. Sonny came to the Blue Room to tell him that Donald Colby who sold drugs to her school was arrested but Cobb felt it was too late. Soon after she died.
Taking it really hard, Jack was given an extended family leave and was supported with his brother and requested no visitors. Learning this, Sonny called him and expressed his condolences.