By 1896, Josie Bassett was heavily involved in a relationship with Elzy Lay, Cassidy's closest friend. Josie had also become involved with Cassidy shortly after his release from an 18-month prison sentence, during which time Ann was involved with Ben Kilpatrick. When Elzy Lay began a relationship with a woman named Maude Davis, Josie became involved with Will "News" Carver, and Ann returned to her involvement with Cassidy. Through their relationships with the outlaws, and in exchange for their supplying the outlaws with beef and fresh horses from their ranch, the two sisters were in a position to get assistance from Cassidy and his gang in dealing with certain cattlemen who were pressing them to sell.