Josie and Ann were good looking young women, and both had a wild side. By 1893, Ann Bassett was involved romantically with Butch Cassidy, and Josie was involved with Elzy Lay, Cassidy's closest friend. When Cassidy was sent to prison for 18 months, starting in 1894, Ann became involved in a relationship with Ben Kilpatrick. By the time Cassidy was released, Will "News" Carver had become involved with Josie, who ended their relationship when Carver became involved with female outlaw Laura Bullion. Josie in turn became involved with Cassidy until Cassidy again became involved with Ann.