When Kerryn Phelps first spoke to Australian Story in 1998 she was a celebrity TV doctor with no public political aspirations. Twenty years later she defied the odds to pull off the upset political victory of the year, winning former Prime Minister Malcolm Turnbull’s blue-ribbon Sydney seat of Wentworth as an independent following his departure from politics. But making history is nothing new for Kerryn Phelps and wife Jackie Stricker-Phelps. Dr Phelps was the first female leader of the Australian Medical Association and is a long-term community health educator and same-sex marriage advocate. We join Kerryn Phelps and her family and friends behind the scenes to learn about the extraordinary personal events leading to her new career in Canberra and ask: can she win Wentworth a second time when next year’s federal election comes around?